From Southie to Santa

An excerpt from the upcoming memoir of Santa Claus, “From Southie to Santa: A Life on The Christmas Run”, published by North Pole Press

Chapter 1

The Day That Changed my Life Forever

I remember the day I took the job of Santa Claus like it was yesterday. It was three weeks before Christmas, nineteen thirty-two. I had just finished my shift at Filene’s Department Store on Washington St and was rushing to join the boys at the speakeasy, The Rabbit Hole Tavern, to have a few pints and listen to the Bruins game. The missus was working a shift at the hospital until eleven, so I had enough time to unwind with the fellas and get dinner on the table when she got home.   

Though it was Christmas season there was not much cheering going on. Nineteen thirty-two was one of the worst of the Great Depression – since the crash in twenty-nine. By the end of the year, the jobless numbers were something like twenty-five per cent across the country. People were sleeping in the streets, families were lining up to get a meal, and humiliated men were taking their own lives.

Things were not as bad in Boston as in other places but finding enough regular work to pay the bills was a stretch for me and my pals. The good times rolling in the “Roaring Twenties” kept on rolling right off a cliff. If thirty-two was any indication, the thirties were promising to be a big wet blanket.

Despite the tough times all around, downtown Boston was lit up with Christmas lights. At the Downtown Crossing, the big department stores were doing their best to perk up the dingy mood, no doubt hoping people hard done by would still open their wallets for the season. By year’s end, the outlook was what the newshawks at The Globe called “cautiously optimistic.” People were putting on a brave face, though most were itching to see the back end of that crummy year.

Franklin D. Roosevelt had just whipped Herbert Hoover in the Presidential elections by promising to turn things around for working people. For a politician he seemed like a good egg who gave a lick about the fact us Regular Joes everywhere were getting the bum’s rush at every turn. Democrats were never the cat’s pajamas in conservative-minded Massachusetts, but Frankie won our hearts with vows to repeal the Eighteenth Amendment – better known as the Volstead Act that led to Prohibition.

Me and my pals could not get to the polls fast enough. We had nothing against the political types, but most of us were working stiffs without the clout or greenbacks to have the blowhards singing our tune. Frankly, we had no time for them. We were not dimwits who expected a politician to do something for nothing. In Southie, the only time a politician came knocking was with a cap in hand to collect his fix.

When me and the boys voted for Frankie it was the first time we put our trust in a politician without being paid or squeezed by the Brunos working the grift. We were tired of sneaking around to have a drink; being shafted by the mobs running the speakeasies. Prohibition was a cruel joke cooked up by the bluenoses; something that seemed like a bright idea in places chock-a-block with bogus bible-thumpers and nutty notions about what the hooch did to immigrants, blacks, and Catholics.

From somewhere in the wheat fields Mrs Grundy and her dry camp believed sicking the Feds on honest, hard-working city-folk for having a swig would clean the country up. The truth is the Prohibition gambit was a golden egg for mobs everywhere. In no time, the big cities were a mob racket where giggle-juice flowed like Niagara Falls and filled gangsters’ pockets with liquid gold. The Depression made things worse; young guys with no prospects drowned their sorrows in plonk or flocked to the only paying jobs they could find: with the crime gangs thumbing their noses at Prohibition.

I took the odd job rum-running for Frank Wallace’s Gustin Gang – not the hijacks of Charles Solomon’s or Joe Lombardo’s merch, but getting shipments of bootlegged hooch from the big rigs anchored just outside the twelve-mile limit to the Southie shore in souped-up speedboats. One of the rum-running bastards put airplane engines in his boats to give him the leg-up. Nothing the feds could put on a boat could catch one of them. My best pal Ducky was an out of work fisherman who lent his family’s boat and his sea-faring abilities to the cause. Me and Kicks, my other best buddy, were his trusted hands on-deck.  

For us, a vote for Roosevelt was a vote for an honest drink at a fair price. If we were going to be sitting on our thumbs, we might as well be able to get smashed with our pals without being tossed in the can. We were also tired of getting clipped for the bathtub gin at the drinking holes the mobs were running. Legalizing alcohol would make our scratch go further and nix, once and for all, the chances of going cross-eyed or rotting out our guts from the hinky moonshine some of the lower-end juice-joints were serving.

Despite the hard times, I had a roof over my head and three squares a day. This was mostly thanks to the wife who had a full-time job as a nurse. The whole arrangement made me feel more tied to my old lady’s apron strings than I already was to begin with. My Jane was the best filly a fella could nab; let alone a dirt-eating Southie grub like me. I was bug-eyed the moment I saw Jane Putnam, and she had her hooks in me the second we met.

The only snag in our fairy tale was the fact Jane was a top-shelf, Protestant gal who came into the world cushy from the get-go; in the gilded lilies of Beacon Hill. Meanwhile, I was a fatherless, Irish Catholic grub who fell off a turnip truck and rolled into a Southie alley. Our love affair was a real-life Montague and Capulet sort of thing. Jane’s father, who I called O’Putnam, hated my Mick guts with every ounce of his Protestant-blue blood. The feeling was mutual.

That said, the tea-totalling WASP prick loved his Lady Jane to the moon. He opened his wallet to see her smile, even if he was convinced the no-good fink who handcuffed her might blow it on whatever the high-hats on the Hill figured us dew-dropping Southies did for kicks. Having to hitch a ride on O’Putnam’s jack was a knock to my pride. Every dollar of his sat in my pocket like a lead brick. Jane’s ma liked to joke how me and the pesky bastard were shackled at the hips: both of us would eat our own crud to see our girl-Friday smile.

The part-time gig at Filine’s Specialty Store just before Christmas was a lucky break. I could buy Jane something nice for Christmas without having to hustle with the gangsters. More satisfying was to look O’Putnam in his peepers after dishing about what a no-good bum I was and tell him he could keep his daisy paws in his pockets. 

I just had to keep away from the gambling tables Mickey The Screw was running. Gambling, and the false promise of easy money, was one of my weaknesses. Mickey was one of Frank Wallace’s underbosses who ran various retail enterprises in Southie while Wallace was busy rum-running and ripping off the Jews and Italians.

Frankly, the jobs with Wallace’s bootlegging boys were getting risky for a guy like me. I grew up in Southie with the crews, but my mojo came from using my noggin, not doing street gigs. My Ma used to say if I was born and raised on the other side of town I could have been a Harvard guy, except I had no interest burying my nose in a bunch of dusty books. I was anxious to get my papers and do some hands-on work for good money.

When the legit jobs dried up, I tagged-along with the Gustin crews when they needed extra hands to load and unload the rum-runners, that’s all. I kept my head down and my nose clean for a quick, easy buck, but I had career plans besides being a big-shot gang-banger. Unfortunately for me, The Depression had other plans.

Wallace was starting to get daring with his rip off hijinx, snatching truckloads of Solomon’s and Lombardo’s bootlegged hooch right on their turf. It was like he was rubbing their noses in it. His guys would dress up like coppers – buzzers and all – and make like they were pinching the loads, then hop in the trucks and high-tail it back to Southie with the liquid loot.

It was a greaseball move nobody expected the Italians would put up with. We were all looking over our shoulders for the donkeys from the North and West sides we were convinced would be coming to Southie looking to crack some skulls. Frankly, the beefs between the goons were none of my beeswax, but I felt implicated because of those rum-running jobs.

Unlike the Jews and Italians, who had connections to good-quality, legit booze in Canada and Europe, Wallace could not get his mitts on his own supply. The Irishmen in on the bootlegging racket were not rubbing shoulders with the street rats in Boston. Guys like Joe Kennedy, Danny Walsh, and Bill Dwyer of “The Combine” were high-level booze dealers.

Everyone in Southie alive at the time knew the skinny: Kennedy was neck deep into bootlegging. I never understood why he made such a stink about his hand in the racket. We loved the old dog for it. It’s obvious the Combine probably saw the Gustin Gang the same as everyone else: like a bunch of dirty, Irish pugs.  

Wallace had to settle for the mangiest part of the bootlegging racket: rum-running from Smuggler’s Alley to the Southie shore and supplying the speakeasies. That, and running dives that had to pay a middleman for their guzzle and serve their customers dolled-up bathtub gin to make a good margin. It made Wallace stark raving mad to not have a piece of the real action. Heisting and fencing were his specialty before Prohibition, so it was a no-brainer he would rely on his old tricks to butter his bread. 

Just before Christmas in thirty-one, the Italians had the biscuit with Wallace filching their merchandise right under their noses. It’s not like they could run to the cops to have someone tossed in the hoosegow – Wallace had most of the coppers in his pocket anyway. For all the bank jobs and such he did in the twenties, he barely saw the inside of a cage. His pals in the precincts fixed things up for him.

The Italians knew the skinny: they had to settle their beef with Wallace gangster style. They could invite the Gustin guys over for some noodle juice and bumping gums – maybe insult each other’s mothers, sisters, and molls for a little satisfaction – until they sealed a deal with a shit-eating grin and an icy handshake. Or, they could drop a dime to their button men and get the cemeteries clearing out spaces for the Chicago overcoats coming their way.

A few days before Christmas in thirty-one, Joe Lombardo asked Wallace and his top-dogs Dodo Walsh and Tim Coffey for a jib-jab to one of his North End storefronts. Wallace was wise to JL’s scheme, so he and his guys stuffed their floggers with pistols fixing to punctuate their arguments with lead. It was a gutsy gambit, but also half-baked to think he could ambush a guy known for making ghosts of his enemies.

Wallace and Walsh did not stand a chance. They were filled with daylight by the Italians laying in wait. By some miracle Coffey dodged the flying bullets, but he saw the light that day – it was shining over the North Side. It was curtains for the Gustin Gang and benvenuti to the Sicilians. Not until the Winter Hill Gang came along in the sixties would any of the rackets in Boston be topped by an Irishman.

With the Gustin Gang in the history books, the crews in Southie were still Irish, but the guys pulling the strings were Italians from the North – guys as far away from Southie as Vatican City. Me and my pals never had a beef with the Sicilians. They were our Catholic kin in a city where the Protestant stuffed-shirts closed ranks to keep riff-raff like us out of their business rackets. They were working class immigrants, just like the Irish in Charleston, Roxbury, and Southie. The Irish and Italians may not have spoken the same tongue, but thanks to the hairy eyed WASPs, we both lived on the wrong side of the tracks.


The construction trades were hit like a sack of bricks by the Depression. Housing starts and commercial building projects ground to a halt in the past couple years. Boston’s once booming textile industry was moving south where the labour was cheap – and black, thanks to prison-labour and Jim Crow. Buildings and warehouses in Boston were emptying out and nobody needed my skills to re-purpose the vacated premises or put up new ones.

I was feeling more and more trapped into the mob rackets to make my bread and sore as hell about it. Other than my one buddy on State Street, the ringers were the only connections to good-paying work I had at my fingertips. My usual good nature was fraying at the edges.

People called me “Grouch” because it was ironic; I was always good for a laugh, even in the most unexpected circumstances. That year, the moniker was more true to reality as life kicked me in the shins with its steel toed boots. Mayor Curley’s big ideas about throwing more money at big public works projects was starting to look like a losing ticket. Building bridges and roads to an economy going nowhere was a mug’s game and everyone knew it.

It was luck, pure and simple, that got me a job as a “Fleen” – what folks working at Filene’s Specialty Store were called. My Southie pal, a big-shot with the suits, rubbed shoulders with the owners and tipped me off about the job. They were dizzy for good builders, which they needed for their Christmas displays. Every year Filene’s flexed its muscles with Jordan Marsh across the street for bragging rights about whose Christmas get-up was the cat’s pajamas. “I’ll stake my name on puttin’ in a word for youse Grouch. You’re a whiz so don’t screw it up with the Southie mugs like ya been doin’, read me?” he said.

I read him.

The problem was that, in between real carpenter stints, the only jack coming in was for those jobs with the rackets. It was a gravy train, and almost risk-free since the Wallaces – even without Frank – still had the cops and politicians in their pocket. If the Feds pinched us Southies on the water, the fixed-up locals would make sure we never saw time in the jug.

Nonethless, I was always wary about taking con-jobs, even when it was run by my old pals from South Boston High. It was a waste of my skills and like giving ammunition to Jane’s old man he could use to disparage me as a no-good crumb. After Wallace got whacked, the business was changing. More of the crew leads barking orders on the bootlegging jobs spoke with an Italian drawl that hit my ears like a bag of Roma tomatoes. There was no way I could trust Luigi or Beppi would not rat me out if we got pinched.

The Filene’s gig was legitimate work at a time when I was getting queasy about rum-running. There was no telling whether I would be kept on beyond Christmas, but I did my best to impress the coneheads running the joint. The rest depended on the economy. It was the first time in my life I was putting my hopes in the word of a wind-bag. If Roosevelt could do what he said he could do … maybe, just maybe.

Filene’s was one of Boston’s flagship retailers. It was in the same class with names like Jordan Marsh, Shepard’s, and Gilchrist’s. The main store on Washington St. was built in nineteen-twelve and designed by the best department store architect in the country, Daniel Hudson Burnham. It was a thrill to work at a first-rate establishment – and get dibs on the deals in Filene’s Basement; a place known by tourists all over the country for its mark-downs on brand-name items. Digging through those ransacked bins was like panning for gold.

I remember fighting a chill that night; I forgot to bring my scarf and mitts to work that morning. It was warm when I set out for the day, but the weather changes in a snap in Boston in early winter. I usually checked the weather before heading out the door, but that morning I was distracted; not only were Jane and I awake at the same time in the morning but we were in the same place. We took advantage by hitting the sheets for a little bump and tug, so I was running late when I raced out the door.

A cold snap rushed in over the course of the day. I never noticed just how cold it was in the short walk from Filene’s to the subway station downtown, but when I got off the Red Line at Broadway station in Southie it only took walking a couple of blocks until I was frozen all the way through to my gizzards. I was cursing myself for being such a moron. People must have thought I was a mad-hatter yelling at myself like that.

I was anxious about catching a chill and getting sick. I had big-time debts to pay and could not afford a day off.

I got a wiggle-on to beat the cold, double-timing it down Old Colony Street to the Rabbit Hole. The Bruins were playing the Americans from New York in the hockey game that night so the tavern would play the radio broadcast. The Depression was bad enough in thirty-two, so it was like a kick in the keister when the Red Sox also had their worst season in franchise history that year. When all was said and done, they had twenty-seven point nine per cent winning average. The curse of Babe Ruth …

Our hopes for something to cheer, besides being able to buy a legal drink again, were riding on “Dit” Clapper and the Bruins. We were desperate for Dit to bring home the cup, which we had last won in twenty-nine. Maybe he could recreate the magic of the legendary “Dynamite Line”, which also included Cooney Weiland and Dutch Gainor. They were one of the first lines in the NHL to be so good they got a nick-name.

I stopped at a street corner waiting for a light to change when I looked up and saw a Lucky Strike billboard. Jane, who was a nurse, had a bone to pick with cigarette marketing ads, which were filled with hooey about the medical benefits of cigarettes like stress relief and weight loss.

The billboard that night showed a minxy dame casting a “come hither” glance over her shoulder to her Johnny-come-lately sitting at the table. The bubble caption read, “Light a Lucky and you’ll never miss sweets that make you fat.” At the bottom of the billboard was their slogan, “It’s toasted.” The only thing toasted was Jane’s temper.

Next thing I knew, I was patting down the pockets of my overcoat searching for my pack of butts, figuring one would help take my mind off how cold I was. I was kicking bunnies when I realized I rushed out of work so fast I forgot to grab my Camels.

Just then I felt a tap on my left shoulder. I turned my head and saw, in the corner of my eye, the top of a pack of cigarettes with one popping out of the opening. Funnily enough, it was a pack of Camels.

“Smoke?” a growly voice chuckled from behind.

When I turned to face the charitable stranger I was shocked at what I saw: two snazzy gents, one who was a real sheik, the other a pudgy goon who looked like a gristly tree stump with a head and limbs.

The sheik was well-built with swanky, coiffed blonde hair and deep blue eyes, which glowed beneath the shadow thrown by the rim of his posh, felt halt. His face was clean-cut and chiseled; his teeth were white like fine china. His teeth beamed in the light from the streetlamps. He had a friendly, toothy smile from ear to ear, like he just told the best gag in the world and had everyone in sheets. He wore shiny leather gloves and carried a smart looking briefcase in his right hand.

The greaseball’s hair was slick – I could tell even under his jazzy lid. He wore a thin moustache above his upper lip that made him look like a dip; stunning you with his pearly whites while hawking your wallet with one of his two left hands. His skin was greasy and pasty like he was a fry-cook at a chip joint. He was sucking wind a little; I gathered because he had to keep up with me – a six-foot-something bean-pole – when he had cocktail weiners for legs.

I was dying for a puff, but on the fence about mooching anything from the likes of the greasy stump. I could see the strings attached from a mile away. It was bad enough Mickey and his ringers got their hooks in me before I got wise – I did not want to grab the rope this lug was going to use to hang me with later on.

The only thing the two gents had in common was their glad rags. They were both dressed to the nines. They looked like they just stepped out of a limo with Carey Grant and Greta Garbo; like big-shots on the silver-screen – starring in a gangster movie.

I began to worry. I was in for two-hundred fifty bucks with Mickey’s crew, a lot of cabbage for a working stiff like me. I could usually hold off Mickey’s pugs – they knew I was good for it eventually; that I was taking jobs rum-running between stand-up gigs. The Brunos pulled my dance card just to let me know it was high time to settle my account. Once in a while one of the ding-dongs would pop me in the kisser for good measure, but Mickey always had words with them for doing it. After all, me and The Screw were chums since we were playing tiddly-winks on Dorchester.

But things were changing in the New England rackets. Since Wallace got whacked, the Italians were the big bosses in Southie. Heck, the Italians were closing in on all the rackets in New England and the East Coast. They were even putting the screws on “King” Charles Solomon, also known as Boston Charlie, who ran speakeasies from the West Side. The word in Southie was King Solomon’s days were numbered. Maybe these two hoods was the sign of things to come; that the Italians were taking over the collection of Southie’s accounts.

I had a head for counting cards and figured I could use my skills at the poker table to get a few extra Lincolns in my pocket for Christmas. Having to be so chintzy for lack of lettuce made me feel like a first-class loser. At first, I was hitting all sixes and quickly found myself up three hundred bucks. Like a fool, I fantasized about O’Putnam’s Limey mug spastic from shock as he watched Jane tear open her fine and fancy Christmas gift from yours truly.

Unfortunately, my luck vanished faster than a bible in a bordello. Someone must have cottoned on to my gambit and ratted me out to Mickey. I figure the only reason Mickey didn’t break my legs right off was because we ran together as kids in Southie. Instead of sending me home with a couple of digits short of a fist, Mickey figured it would be fun to get his hooks into me instead. Me and Mickey were always like that; I would razz him, and he would find a way to kick me in the pants without it being his foot doing the kicking.

On later reflection, it was obvious Mickey had guys in his crew who could count cards better than me. In no time flat, I was a hundred in the red. I figured I could crawl out of my hole the honest way – I was still a card shark, counting or no counting.

I figured wrong. In the game that did me in, I had the hand to beat all hands – or so I thought. I doubled down on my bet and called it. It turned out to be what Mickey later called an “ill-fated move.”

So, here we were. The bosses in North End had sent a couple of toughs to do Mickey’s dirty work. I knew the Italians meant business – they took care of Wallace and Dodo all right.  

Did I want a smoke? Damn right I wanted a smoke!

The short one was all balled up. The sheik frowned and gestured with his head, as if to say, “Maybe he’s deaf or something.”

“Hey pal, you go somewheres?” shrieked the ugly stump.

I was startled from my thoughts. “Uh, yeah … sure. I’ll take a smoke. You gotta light?” I said, reaching to grab a smoke.

“Full service for this one, huh Joey?” the ugly stump said.

He spoke with a thick Italian American accent; different than the mugs from Lombardo’s crews in the North Side, but definitely Italian-American. I nick-named him La Stumpa, which, in my mind, struck the right balance between being Italian and insulting.

“Ach, Tony not ze Joey!” said the sheik in strongly German-accented English. It was obvious he was no fan of La Stumpa’s moniker.

The sheik reached into his side pocket and whipped out the shiniest, classiest gold lighter I had ever seen. He spun the flint, igniting a tall flame, and sent it towards me slowly and gracefully – with the air of someone who grew up in the Kaiser’s castle. The nickname that came into my head: Wundershiek.

I leaned forward with the cigarette in my mouth and took a few long, strong pulls. I sucked that butt like it was my last breath, sending a cloud of smoke past La Stumpa’s face. If these goons were going to stick me in a meat wagon, I was going to get in some licks wherever I could.

“So … you guys from Lombardo’s crew? Tell ‘em I says vavanguli, or however youse guys say get outta my face,” I said. I was puffing out my chest for show. In reality I was spooked so bad my knees were shaking.

Wundersheik smirked. He knew what I was getting at. “He sinks we’re ze debt collectors!” he said.

“Look again kid. We look like a couple of greasy hatchet men?” La Stumpa asked.

I took a drag of my smoke. Except for the clothes, La Stumpa did look like a high-end hatchet man. The sheik, on the other hand, suggested these guys were something else.

I shook my head.

La Stumpa slapped me on the shoulder. “You got some moxie double-crossing a son-of-a-bitch like Mickey The Screw!” he said.

I was relieved, but a little chagrined these two high-end gents were wise to my low-end problems. “Where you fellas from?” I asked, changing the subject.

“I’m originally from Brooklyn, but for the last couple-a decades, how can I say this … me and my confrère Johan here … we’re from the North Pole. Name’s Tony Tagliatelle – like the pasta,” he said. He pulled off his glove and extended his hand.

“North Pole, huh? Everyone’s a comedian,” I said.

“Nein, Meister O’Rourke! No comics. We are offering you ze job as Santa Claus!” Johan said.

The look on Johan’s face was a mixture of desperation and excitement, like he just told me I was the long-lost, first born son of the King of Spain who was dying and needed my hide pronto to keep the throne warm.

“Yeah, we were sent here to recruit youse as head of Christmas operations,” Tony said.

“Head of Christmas operations huh?” I said.

Wait a minute. This is Ducky, Kicks, and the rest of the gang getting me back for all those times, I thought.

I decided to play along.

“So, Christmas operations. What are we talking about, here? Telling Frosty to keep his carrot-topped dingus to himself? Making sure Jack Frost stays lost? What gives?” I asked.

Let’s see how the hired jokers think on their feet.

“You’re a riot, O’Rourke! Nah, all that Frosty and such is a bunch a crap. We need guys with chutzpah like you in the big chair to protect the image of Santa and the spirit of Christmas against the scumbags trying to own the racket,” Tony said.

“Like those crooks and bastards at Macy’s!” I said, pretending to be as indignant as Tony.

“Jah Wolt!” Johan exclaimed.

“So, you aren’t a couple of recruiters from Macy’s then?” I asked.

“Nah kid. We’re the Real McCoy,” Tony said.

For love of Mary and Joseph these guys were relentless! “So, what’s it pay? If I’m running the joint there should be a pile of shekels in it, right?”

“How’s twenty-five large a year sound?” Tony said.

“With yearly increases for ze increasing cost of life,” Johan chimed in.

Get the fuck outta here!

Now they were playing with my emotions; telling me I was going to make ten times what I made in twenty-seven – my best year ever. I brought home twenty-five hundred bills that year, which made me as happy as a fat kid in a candy store. Now these bozos hired by my pals to razz me were waving fairy tales in my face like the Depression was a big joke.

“Let my esteemed colleague and I give youse a lift to wherever you was heading,” Tony said.

“You gonna take me in Santa’s sleigh?” I asked. I was starting to get annoyed with the antics.

“Nein, mein Freunde, in zat,” Johan said, stepping aside so I could see what was behind him on the street.

Everything on the metallic red Hooper Rolls Royce parked at the curbside glistened: the white wall tires and rims; the chrome grill, bumper, and headlamp assembly; the runners and door fixtures. Until that moment, I had only seen one of these rigs in the pictures.  

“That’s your ride?” I asked.

Tony smirked. “That’s your ride – if you take the job. Lemme guess, you was heading to the Rabbit Hole, weren’t ya?”

“Seriously, now. Who sent you jokers? Was it Ducky?” I was getting tired of the song and dance.

“We are seriously two agents sent to offer you the job of a lifetime. Come for a ride and we’ll tell youse all about it,” Tony said.

I took a last drag of the cigarette and tossed it to the ground. “It’s been a slice. Thanks for the smoke gents,” I said, and made tracks down Old Colony to the Rabbit Hole as fast as my hocks would go, hoping to leave the riff-raff in my dust.   


It wasn’t the first time people got to thinking I would make a first-rate Santa Claus. Folks said I had a look. People were always complimenting about what a stand-up guy I was, even when I was getting my digs in. I flapped my mouth when I was sore about something, but I was what Jane’s ma called, “one of the good ones.” My only detractor was O’Putnam, who thought I was worse than a wad of chewed gum stuck on the bottom of his shoe.

When I was in a jam with Mickey and his crew back in the day, I cracked a joke instead of resorting to fisticuffs. Not that I was a drip, but I liked to settle scores without burning bridges. I thanked my lucky stars I took that approach with Mickey all those years ago. If I had smacked him around when we were little kids, and Lord knows Mickey had a way of making a guy want to punch him in the kisser, I would have already had a limp to show for the two-fifty I owed him.  

I managed to shake the mismatched elves from Santa’s Workshop by the time I made my way down the long, dark alley with the hidden entrance to the speakeasy. I did the secret knock on the door and cringed as the hatch to the speakeasy grill slid open – rusty metal on rusty metal.

A pair of angry blue eyes were staring back at me, scanning me like I was the dodgiest rat he’d ever seen.

“Hey Bug, maybe some oil for that thing, huh?” I asked.

“Evenin’ Grouch,” said Bug.

Bug was one of those ironic nicknames fellas give another fella for a lark. Bug was a blimp with limbs. A nickname truer to reality would have been Hippo or Dumb Walrus, but there was no fun in that. Bug was miffed by the nickname, which was the point. I used to get a rise out of him, saying, “What’s bugging you Bug?” Mickey told me to cut it out – Bug was fixing to crush me in his meaty manacles.

The speakeasy grill slammed shut and the door flew open. I struggled to squeezed past Bug through the door frame. “Time to start skipping a meal or ten, huh Bug?” I said.

Bug laughed as he lurched out the door to check the alley. He turned his melon like an owl because God forgot the neck when he made Bug. He scanned the scene to make sure nobody who looked like the heat was watching.

I turned and sauntered down the long hallway towards the next door and second checkpoint to the speakeasy. On the other side of the wall was a kitchen for the restaurant serving as a legitimate front for the speakeasy below. I knocked on the door and was checked out by another set of hairy eyeballs giving me a wary look-see. The goons working the doors at these joints were not recruited for their looks or witty repartee, that’s for sure.

I made my way along the winding maze of hallways leading to the speakeasy. A wrong turn would have led me to a basement door to somewhere else – a legitimate establishment, sure enough, but not the speakeasy. The hall of mirrors getup made it almost impossible for the cops to find the place, let alone bust it up. Not that they would have since Mickey and his boys who ran the Rabbit Hole greased the wheel good enough.

I loved the rush of energy at the speakeasy; that was the draw. The jazz cats playing the swing, the flappers and canaries tying it on. Even though I only had eyes for my Jane, it was a hoot to see Ducky and Kicks drooling out their mouths and tripping over their tongues trying to talk up a looker. It brought me back to the good times, not so long before, when every day in life was ring-a-ding.

Being in the speakeasy was like leaving the Depression behind. At the Rabbit Hole a fella could feel like the roaring twenties never ended. The minute my senses caught the whiff of beer and spirits and the hum of live jazz music my whole body perked up. The feeling was like an addiction.

Before Prohibition it was a rare sight to see respectable, married dames hanging out in a gin-joint – or any place that twisted a gentleman’s honour. Once the taps were shut, even classy dames like Jane had no choice but to make an appearance if they wanted a taste of the juice. Jane’s favourite drink was a Mary Pickford, which I thought was a riot. She was risking getting pinched to sneak a drink that tasted like soda pop.

“Empty a keg in my glass, Twitch!” I yelled.

Twitch, the barkeep, got his name thanks to a rotten case of shell shock he got in the Great War. If you sneaked up on him you either sent him running for the nearest corner where he’d ball up like a kid, or you’d end up with a knuckle sandwich. His eyes blinked so fast they could fan a flame; his head cocked and jerked continuously, and he stuttered when he was emotional. Poor bastard saw terrible things in that war.

“Hey Grouch, R-R-Red says it’s d-d-dog soup for youse until you clear up s-s-some of your t-t-tab,” Twitch said, unable to look me in the eyes.

Red was the guy who managed the Rabbit Hole for Mickey’s crew.

Twitch hated to be the bearer of bad news. A guy comes in for a drink and Twitch is the one who has to slam the door in his face. A lot of fellas did not take too kindly to the news flash and threw fists at the poor guy for his troubles.

Not me, I knew he was just the messenger. No hard feelings.

“Lucky I got some scratch then, ain’t it,” I said, slapping a ten on the bar.

Twitch’s face lit up like I just gave him a pair of mint seats to the Bruins game. He poured my pint so tall I had to sip from the top so I could carry it across the room. He gestured with his head to a table to the left of the stage where Ducky and Kicks were sitting. Those two dinks had been my best pals since we were still crapping in our pants and eating dirt because we didn’t know any better.

I came up with most of the nicknames for the guys in our gang. Ducky’s real name was Declan Lecky, a kid who lived over on the next block from me. When we were kids we’d lose track of time playing stick ball until Mrs. Lecky’s shrill voice rang out like an air-raid siren, cursing his name on the cross or yelling, “Get yer bleedin’ arse home to yer ma’am!”

Eventually the screaming would stop, and was followed shortly thereafter by Mrs. Lecky blazing down the street growling in her thick, Irish-accented English, “Jesus, Mary, and Joseph Declan, ye’ve got shite in yer ears!” She would grab Declan by his collar and drag him home kicking like a mustang, imploring the rest of us to, “Stop bein’ the Devil’s idle hands and help your weary ma’ams!” It was like she was giving a union-organizing speech for The Federation of Southie Moms.

One time, Mrs. Lecky pegged Declan in the head with one of his father’s work boots and damn near knocked him out cold. I can still see Ducky’s mess of hair explode in all directions when the boot made contact. His head caulked violently just before his rake-thin body was sent flying through the air. After that, every time Declan’s mom came hollering after him, I’d yell “Duck,” which sent the guys cowering to avoid a flying work boot.

Thus, Ducky was born.

Kicks was the nick-name I gave Ciaran Hennessey. He told strangers was earned because of his skills as a footballer. True enough, he was a fantastic footballer, but we called him Kicks because of what happened with Seamus O’Malley.

O’Malley ran a small general store that sold candies of all types. He was the nicest old man you could meet; we joked he was the closest thing to a living leprechaun. Except for one thing, that is: the darkness lingering in his soul. The fire that kept his seething rage alight was ignited by the Potato Famine, which he experienced as a young child. My ma said Beelzebub took hold of him when a child crossed him; it was as though he believed he had been betrayed by a kindred spirit.

O’Malley was fairly good-natured about us kids stealing the odd gum ball or licorice when he was not looking. For some reason, he had a hate-on for Ciaran since the moment he heard his name. We figured the bad blood had roots in a feud that began in the Old Country and sailed across the Atlantic with the migrating families. It was not an uncommon thing, which struck me as ridiculous given the common foes we all shared: WASP bigots and anti-immigrant hostility.

One day O’Malley spied Ciaran shoving a couple packs of gum in his pants pocket. The old man leaped from behind the counter like a mongoose poised to kill a cobra. “I’ll kick the feckin shite into you, you thieving little cunt!” he shouted, before planting a bone-crushing kick in Ciaran’s unsuspecting arse.

It was the first time I had ever heard that word.

I asked ma later on what ‘cunt’ meant. She had the bar of soap halfway into my mouth before I could tell her where I heard it. Ma said it was a vile word for a lady’s private parts; that it was worse than if you’d taken the Lord’s name in vain or mentioned the King of Bastards – who the WASPs called King George – in an Irish household.

Naturally, I asked what the proper word was for a ladie’s private parts. Ma slapped me upside my head and said, “The proper word is ‘I Do’ you bleedin’ demon. On your wedding day is the time to go on frettin’ about that sacred place, and not a day before.”

The nickname ‘Kicks’ was our way of paying homage to the precious moment when Ciaran got his ass kicked so hard he could not sit for days and got called a lady’s privates. We also grew up believing there was something sacred about a lady’s vagina – at least until we knew better. Later on, we turned our childish gullibility into dirty jokes about how a fella who worshipped a vagina with devotion could expect to be blessed with pots of gold and possess the magic of the Blarney Stone.

“Cheers fellas! Score in the game?” I asked.

“Nothin’ to nothin’, Grouch,” Ducky said. He looked nervous.

“Mickey’s crew was just here lookin’ for youse. You been on the dice again, Grouch?” Kicks asked.

“Nah. Cards. Any of you fellas got a cigarette?” I asked.

“That bad, huh,” Kicks said.

Ducky slid a pack of smokes across the table. I rolled my eyes, “Lucky Strikes? Really?”  

“He’s tryin’ to lose weight,” Kicks joked.

“Gimme a break fellas. I lifted ‘em from the old lady. Ain’t seen you complainin’,” Ducky said.

Red barged into the speakeasy with a couple of heavies trailing behind. The three men headed straight for our table. I had seen the two guys before – they were Mickey’s crew. He had sent Pick, who was always chewing on a toothpick, and Boots, whose nickname was also his favourite tool for collecting accounts. These mooks were Mickey’s surliest collection agents.  

“Hate to do this Grouch, but I don’t want no trouble with The Screw. These fellas say they got some business to discuss wit’ youse,” Red said.

Most guys got the nickname Red because they had red hair, or freckles, or rosy cheeks. Not Red, who was as bald as the day he was born and was more blue than pink or red in skin tone. Red was as hot-headed as a mule in heat. He was always pissed off about something, and when there was nothing to be pissed off about, he found something.    

“Don’t be a couple of pills. Let a fella have a sip will you,” I said, trying my best to make light of the situation.

“’Fraid not, Grouch,” Pick said. He quickly shuffled in behind my seat.

“Yeah, time for a heart-to-heart Grinch,” Boots chortled.

 “That’s Grouch, you friggin’ moron!” I said, raising my pint to my mouth.

I managed to get a half-slurp of beer in my body when Pick grabbed me by my jacket and raised me to my feet.

“Alright Mutt and Jeff, take it outside!” Red yelled.

Kicks and Ducky stood up, shoving their chairs out of the way. Next to Jane and my mother, there was nobody I loved more than those guys. I did not want them to risk breaking their necks fighting for my honour, which in this case, was as tainted as a single in a Scollay Square burlesque joint. Mickey’s guys were just doing their job, and I deserved what was coming to me.

“It’s all right fellas, me and the aces here are gonna have a jaw, figure out how to nix this depression in the bud once and for all, ain’t we?” I said.

“Whatever you say Grouch,” said Boots, who was pounding his fist into his open hand.

“Anything happens to him and we’re coming for youse,” said Ducky.

Ducky was no slouch. He was a fifth-generation fisherman who could toss a tuna over his shoulder like it was a bag of potatoes. His hands were bigger than my head.

“Take it up with the boss,” Pick said, laughing.

It was the longest walk out of the speakeasy I ever took. I had never been in this deep with Mickey for anything. The guy manning the exit, a jumble of jiggly whale everyone called Clump, had the look of a Holy Man giving last rites to the condemned as he sauntered to the gallows.

I thought of making a run for it as soon as we reached the alley. Then I thought, Where the frig are you gonna go, you moron? They know where you live. You wanna be on the lam from a goon like Mickey The Screw your whole life?

It was time to face the music. Not the good music, which got the flappers happy, but the kind of music that came with pall bearers and black lace.

Boots grabbed me from behind and slammed me hard against the brick wall.

Pick shook his head, plucked the toothpick from his mouth, and tossed it to the ground. He nudged his face right close to mine until our noses were an inch apart. His breath smelled like minty cinnamon, like my ma’s favourite tea.

“You ain’t gonna kiss me are you? I should warn ya, my breath ain’t swell like yours. I had anchovies for lunch,” I said.

“I’m glad this is fun for youse, Grouch. It makes it a whole lot easier,” Pick said, before plunging his meaty fist into my guts like he was trying to knock my spleen out my back.

I buckled to the ground as every ounce of air escaped my lungs. I gagged and struggled to take a breath. “I woulda preferred a kiss,” I said, wheezing.

“That could be arranged,” Boots joked.

“No thanks Bimbo, oil cans ain’t my taste,” I said.

That ain’t gonna help, I thought.

Being smarmy is what I did best when I was pushed into a corner. When I figured the jig was up, when fate already made up its mind, my mouth was like a shovel come to dig my grave.

My ma used to say, “Even a rabbit will take a chomp out of the one who gives it no quarter,” – most often just before she gave me a licking for something. Unlike a rabbit, I kept my teeth clean and bit with my gums instead.  

I could smell Boots’s blood boiling – a combination of rabid dog and unhinged idiot. “Let’s see what else you got funny boy!” he said.

Next thing I knew Boots’s infamous hocks were waltzing on my ribs. For his second act, he smacked a couple of kisses on my map and was gunning for an encore with a romping, stomping square dance on my sternum when Pick got merciful and intervened.  

“Cool it Boots!” Pick yelled, pulling Boots by the back of his coat and tossing him aside.

Pick bent over me and wiped me up off the ground. He stood me against the wall and dusted me off.

“Come on Pick, let’s show the welcher how fun it is to welch,” Boots said.

I wanted to say something about his crummy comeback but decided against it. I had snatched one too many bananas away from angry apes for one day.

Pick opted to send his message with body blows. He knew it would be bad for business to leave a debt-ridden bum looking like he washed his mug against the pavement, which could get him fired from the job he needed to clear his account.

Boots was too thick in the skull to get with the program. When God was giving out brains Boots was waving his Johnson with one hand and doing push-ups with the other. Thanks to him, I was going to have a shiner, a fat lip, and a goose egg just in time for the family Christmas pictures. Jane was going to have a fit. O’Putnam was going to ding me with a barrage of the latest, new-fangled WASP slurs for Irishmen.

“You fellas mind if we cut into this dance?” yelled a voice from the end of the alley.

I was seeing stars from Boots’ laying a beating into me. I could only make out their silhouettes, but it was unmistakably Santa’s swanky elves from earlier: Wundersheik and La Stumpa.

“Yah, ve vere first on ze dance card,” said Johan.

“Take a hike Mack!” Boots yelled. He stormed toward them with both his fists clenched, spoiling to give the two jazzy Jakes a piece of the same humble pie he just gave me.

“We got ourselves a bruiser!” Tony yelled. With a smirk pasted across his face, he walked toward Boots like he was taking a leisurely stroll through Boston Gardens.

Boots cocked back his fist, fixing to send Tony to the next planet. Tony reached his right hand into a side holster under his left arm and pulled out a glittering, silver pistol. My eyes were like saucers – I thought I was about to see a guy get smoked.

Like a gunslinger in a Western picture, Tony turned the pistol around in his right hand and struck Boots in the side of the head with the butt end. Boots crumpled to the ground like a dirty shirt.

“Tisk, tisk. Zat’s going to leave ze mark in ze morning,” Johan said, shaking his head as he stepped over Boots. “Words are always better zen fists.”

Tony walked up to Pick, who froze while clenching my coat in his fists as he propped me up against the wall. I doubt he had ever seen a guy casually clock one of his meanest toughs like it was a walk in the park.

“I can tell you’re the man in charge. Name’s Tony Tagliatelle, like the pasta,” he said, reaching out to slip a five to Pick.

I noticed the shiny gold watch around Tony’s wrist. His skin was smooth, his fingernails well-manicured. There were no callouses on his hands from holding a broom or a wrench. The whiff of ritzy men’s cologne nearly knocked me to my knees.

Pick let go of me so fast to shake Tony’s hand I fell to the ground hard and rolled on my back. I was still throbbing from Boots using my body like a heavy bag.

“What’s it gonna take to make Mr. O’Rourke here copacetic with Mr. Delaney?” Tony said.

I went bug-eyed when Tony called Mickey by his family name. The last person to try that was Mr. Davis, our grade nine teacher, who earned himself a sock right in the kisser for his troubles. Back then Mickey was Mickey; not mister anything, and definitely not mister Delaney – the name of his deadbeat old man, a bum and a sap who skipped out on his wife and kids. That’s when Mickey earned the respect of his peers. He made good after being man of the house since he was thirteen.

Though Pick was almost twice Tony’s size, he looked like he saw a ghost. I could hear him swallow hard. “Two-hundred fifty,” he said.

“Tsk, tsk, Johnny. Your little boondoggle at the tables didn’t pan out, huh?” Tony grinned.

Tony reached his hand underneath his thick, wool trench coat and pulled out a long, black leather wallet attached to his waist-pocket with a thick, gold chain. There was a thick stack of bills inside.

Tony looked me in the eyes as he licked his fingers and plucked the payola from his wallet. “This ought to take the spin outta Mickey with the joker over here,” Tony said, slapping the bills in Pick’s hand.

“Looks like Saint Nick came early for youse Grouch!” Pick said.

Judging by the grin on his face, Pick was relieved not to have the unpleasant task of giving my kidneys a knuckle bath in a week’s time for my outstanding obligations.

“Here’s a little something for you and Charleston Charlie over there. No hard feelings?” Tony said, slapping down a Ben Franklin in Pick’s hand.

Pick smirked. “Boots has a habit a running into things face first.”

“Auf Wieder sehen!” Johan smiled.

“Hey Boots, you kick like a flapper!” I yelled down the alley.

“A real wise cracker, ain’t you? Your mamma ever tell youse your mouth is bigger than your odds?” Tony said, gesturing to Johan to pick me up off the ground.

“I thought my name was Shut Yer Bloody Hole until I was ten!” I said.

“You are ze funny one, Meister O’Rourke!” Johan laughed, offering me his free hand to help me up.

“A compliment from a guy whose country loves yodeling. So, who’s shoes I gotta shine for the next decade to repay my debt?” I asked, grabbing Johan’s surprisingly massive paw to pull myself off the ground.

“We told youse Mr O’Rourke. The boss says you’re our guy. And by boss I mean the soon to be retiring Santy Claus. Johan and I were sent to make the offer and tie up any loose ends. By the way, you gotta lot of loose ends O’Rourke, if you don’t mind me saying,” Tony said.

Johan lifted up his briefcase and patted it with his leather-gloved hand. “Vat can it hurt to hear ze offer?” he said.

“Drinks on you?” I said.

Tony smiled. “This guy’s a riot!” he said, slapping me hard on the back.

“Can I get a schnapps?” Johan said.

“This ain’t a Berlin Cabaret. Whatever hooch Mickey gets his mitts on is what’s on the menu,” I said.


I escorted my two new best buddies the few blocks back to the speakeasy entrance. Bug gave me the look of death when he saw the two stragglers flanking me. Tony whipped out a ten-spot and flapped it in the air. In the two years Bug and The Rabbit Hole were like my second family, I never saw that surly beetle smile.

Twitch and the guys looked like they had seen a ghost when I returned. I could tell they were sizing up my fancy sidekicks, especially when they noticed my face looked like a raging bull was dancing on it. I gestured to let them know Tony and Johan were on the up and up.

Tony suggested we get a table in a quiet corner where we could talk. I asked if he would mind picking up a drink for Ducky and Kick while he was at it.

“Tonight’s on us Mr. O’Rourke,” Tony smiled.

He asked Twitch what my bar tab was. Tony was like a private dick who knew every sordid thing about me. He shook his head and laughed when Twitch said “F-f-f-forty b-b-beans, mister,” before slapping two hundred fifty bucks on the counter. “First off, clear this man’s account. Keep pouring drinks for everyone till the money runs out. Got it Mack?”

“Jesus!” I said.

“No siree, Santy Claus! Listen up gents! Drinks on the house!” Tony yelled into the speakeasy.

Fellas went nuts.

While everyone spent the evening getting smashed on Tony’s dime, the North Pole’s most gritty, persistent elves gave me the skinny on the job of Santa Claus.

Santa’s palatial home was mine, with kitchen, cleaning, and serving staff. Johan showed me pictures of my “company home.” Best of all, it was ten times the size of O’Putnam’s shack.

When I told them Jane and I wanted to start a family, Johan pulled out a glossy brochure called “Taking Care of Santa’s Family.” It had pages and pages of all the reasons why growing the O’Rourke clan in the North Pole was better than doing it somewhere else: nannies who were formally trained in child-care, early childhood tutors, teachers with alphabets behind their names and sheepskin covering their walls from ritzy places like Harvard and Yale.

I never knew there was such a person called an early childhood tutor. The kids were never going to get that kind of learning in Southie. Not only that, but there were steam rooms, massages, saunas, tennis courts, pools, and tickets to all the professional sporting events and high-end cultural stuff – not that I gave a crap about that. The frou-frou stuff would put a smile on Jane’s face, though. Not only would me and Jane live like royalty, but we could keep ourselves entertained like a couple of big-shots.

It all seemed too good to be true. The problem was I loved being a carpenter. As much as I was having trouble finding a steady job, I knew eventually things would have to get better. I did not bust my hump to get my papers only to high-tail it to the first cushy gig that came along when the going got tough.

Tony said I could have a woodworking workshop and stack it to the rafters with all the machines and equipment my heart desired. I could even start my own manufacturing company if I wanted.

“So long as you do not take advantage of working people and sell at a fair price,” Tony said.

“Whaddya mean by fair price?” I asked.

“Your end price should cover your materials and what it cost to pay you or your workers a good living wage to make the product – plus a little extra to stick in the bank to pad you through the lean times,” Tony said.

“You ain’t a couple a commies like them rabble-rousers Sacco and Vanzetti, are ya?” I asked.

“The Anarchists frying in the hot seat? Nah. And we ain’t Reds like that phoney, nogoodnik thug Stalin. We ain’t into exploitin’ Regular Joes for the robber barons neither!” Tony said, becoming more animated.

“Zat’s why ve need good-natured, hard-working regular volks like you in ze Big Red Chair, Meister O’Rourke,” Johan said, with a glimmer in his eyes.  

“I carry a piece to protect the season from the fat-cats and knuckle-dragging fiends. The bloodsuckers making it hard for regular folks to enjoy the fruits of their labour; who shift the focus of the season away from kindness and generosity! Don’t even get me started on the religious nut-jobs!” Tony exclaimed.

“Jah wolt!” Johan said, slapping his open hand on the table.

“Three double-shots of that Canadian Whiskey over here!” Tony yelled.

No matter how hard I tried, I could neither see nor smell the ‘raw’ in the deal Tony and Johan were trying their best to sell me on. That is, besides agreeing to leave my life in Southie and moving to some far away place whose location was a secret. Even that was not so bad since the job came with ten weeks’ holiday every year.

I caught myself daring to imagine a future without having to crawl on my knees like a jerk to secure a job that paid peanuts. The grim images that had been haunting my mind – of me frantically running to avoid faceless torments, staring down one dark alley after another, wondering which of them might finally lead to safety and security at the end – began to lift.

As I listened to their pitch, visions of me sitting in a wing-char by the fireplace, wearing a cardigan sweater, slacks, and slippers popped into my head. A brood of kids sat at my feet, wide-eyed as I read them Winnie the Pooh or Doctor Doolittle. Jane was on the opposite couch, bouncing the newest addition to the family on her lap, happy as could be. It felt like the vice grip that was closing in on my body for so many years was finally beginning to unwind.

“I can see the glint in your eyes. That’s good. You deserve it. You’re a good man, despite your weaknesses. Take me and Johan up on our offer and the pipe-dream in your head can become reality!” Tony said.   

“You say I can come back to Southie as much as I want?”

“From February through August. September through January you’re gonna be too busy running things to be taking any time off. Trust me, you’re gonna love it,” Tony said.

“So when I’m back in Southie how do I explain where I been all year, every year?” I asked.

“Tell zem you are working on oil and gas development projects in ze Near East,” Johan said.

“Come again? I got no clue what just came outta your horn,” I said.

“Neither will they kid,” Tony said, winking.

It was a great cover-story – or lie, if you will. It was so effective I used it year after year.

When Tony and Johann were done giving me the skinny, there was only one question I was dying to ask. “So, besides dressing up like a moron, shoutin’ Ho Ho Ho all goddamn day, what else does Santa do?” I asked, feeling like I had gone loopy for even asking the question.

“You’re the capo of the whole shebang, mister. The living incarnation of Santy Claus. Boss of the North Pole and all Christmas operations – toys, merchandise, and most importantly, the essence of the Christmas spirit,” Tony said.

“Ze North Pole is a whole organization to support Santa Claus. Volks like us are your humble servants,” Johan said.

“A lotta people wanna take down Christmas, turn it into a money-maker, and hi-jack Santa Claus’s message of love, compassion, and goodness,” Tony said.

“People like Macy’s you mean?” I said, joking.

“They ain’t even the half of it,” Tony said. The look in his eyes was dead serious.

“Ve are soldiers for the True Spirit of Christmas,” Johan said.

“And we want you to be our General. Whaddya say? You in?” Tony said.

I was in. How could I not be? All I had to do was convince the missus to be in too.


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