ONE CHILLY FRIDAY EVENING in November a few years ago, Jimmy Leighton slipped into the crowded Starlight Bar & Grill with two thousand dollars in lottery tickets stuffed in his flannel-lined barn coat pockets.
Jimmy nabbed a booth the bus boy hadn’t got to yet, opposite a TV that ruled over the dingy little Christmas-lights-and-neon-beer-sign world of the Starlight, a relic of the days when the late Whitey Bulger ran things in Southie.
James P. Leighton at thirty was a young old pro who could pick a lock, climb a trellis, pry open a window and silently loot the valuables in a home while the owners slept, never harming anyone in the process – more out of low-profile self-interest than innate goodness.
At five ten, one hundred fifty pounds, the boyish Southie thief had talked and squeezed and sometimes fought his way out of one tight scrape and nasty jam after another.
Tonight was different.
Tonight he might die.
The owner of the little grille, Patrick Donovan, was working behind the bar. Five years older than his friend Jimmy, redheaded Pat was tall, trimly bearded and blue-eyed, a paunch moving in on him.
Jimmy caught his eye and Pat frowned, wiped his hands with a towel, signaled a waiter to fill in, and came over.
Sliding in opposite, Pat asked, “You get the money?”
Jimmy shook his head. “Something better.”
And he began transferring stacks of lottery tickets from his jacket pockets to the booth’s tabletop – forming two uneven piles. Pat’s eyes got bigger.
“What the hell, Jimmy?”
“Fifty-five mil Mega Ball payday tonight.”
“How much d’ya put into this?”
“Whole two grand.”
Eyebrows up now. “And you figure to beat the odds?”
“Guess I have to.”
“Jesus H. Christ!” Pat slapped a hand to his forehead. “Why didn’t you offer Deet the two Gs you had, and just pay the vigorish!”
“Deet’s a lotta things,” Jimmy said, “but a loan shark ain’t one of ’em. This was a straight-up loan, a favor for those jobs I pulled for him. Point of pride with the little bastard – he won’t take nothin’ but the full five.”
“Jesus, Mary and Joseph. He’s gonna kill you.”
“That’s not what he said.”
“What did he say, Jimmy?”
“He said he’d been looking for somebody to make an example of. And I fit the fuckin’ bill.”
“He’s gonna kill you.”
Jimmy flipped a hand at the two piles of tickets. “I don’t think so.”
“You know the kind of odds you’re buckin’? Hasn’t Bernadette told you a million times not to throw money away on these stupid things? She knows numbers!”
Jimmy’s girl, Bernadette, was office manager at Zimmerman Brothers Accounting. And she did know numbers. Among a lot of other things.
But Jimmy just smiled and told Patrick what he always told Bernadette: “Somebody’s gotta win.” And then, as the smile drained from his face, he added, “Anyway, I’m fresh outa options.”
“You coulda come to me. I’da sold my car or something. Bernadette might be able to—”
“Not goin’ there. My problem. Anyway, this’ll work out.”
He shrugged. “’Cause it has to.”
For a while neither of them said anything. Finally, Pat slapped the table. “Okay. Might as well eat. You hungry? Cheeseburger and fries?”
Jimmy nodded. “Tell the kitchen to shake it. The lottery thing’s on in twenty minutes.”
The Starlight owner got up and walked over to the little window that opened onto the kitchen, and put in Jimmy’s order.
Jimmy sat there thinking about that dangerous little prick, Deet, who headed up a Vietnamese gang that had dug into South Boston in the late ’90s.
The gangster’s real name was Đaminh Diệp, unpronounceable to Jimmy and his friends. So Jimmy had dubbed him “Deet,” an idea he got working a straight job for an exterminator, where he learned “deet” was short for the active ingredient in insect repellants like “Off” – N-Diethyl-meta-something.
In Jimmy’s mind, “Deet” was the perfect name for a toxic asshole who seemed immune to both the cops and the other gangs in Boston. The tag had spread to the street and, at a safe distance, stirred laughter when the little gangster rolled by.
“Like you always say,” Pat said, returning to the booth with a couple of beers, “that little bastard would kill your ass if he ever knew you’re the one christened him ‘Deet.’”
Jimmy raised his glass and forced a smile. Pat returned the gesture and smiled resignedly. No more recriminations, no more warnings, not from straight, stand-up Patrick – the kind of Irish Catholic who forgave a pal all his sins.
Pat had grown up in the South Boston housing projects, with their double- and triple-decker homes inhabited by generations of working-class families. His pop, Charlie Donovan, worked for Kevin Weeks, a Whitey Bulger lieutenant. After Charlie’s murder in ’84, Kevin had the Starlight signed over to Patrick’s mom, as kind of a reward for Charlie being a good solider. She couldn’t run the place alone, so Pat and his brother John started working there when they were kids.
In his late teens, Jimmy began frequenting the Starlight and got tight with Pat. They’d commiserate with each other about how South Boston was changing from the old neighborhood they knew as kids – tonight was no exception.
“Look at this place,” Pat lamented, slow-scanning the patrons in his diner. “Wall-to-wall yuppies.”
“I hear you,” Jimmy said, working on the burger and those signature Starlight hand-cut fries.
“Southie’s totally overrun by them now, totally! And I got nothing against them, y’unnerstan’. But, back in the day, when you walked down the street, you knew everybody. Today, I don’t know nobody.”
Jimmy was concentrating on his French fry to ketchup ratio.
“Take Triple O’s,” Pat ranted, referring to the hole-in-the-wall gin mill where Kevin Weeks, Whitey Bulger and Charlie Donovan collected unpaid loans back in the ’80s. “It’s a damn sushi bar now! So many of the old haunts are Starbucks or bistros or health food stores these days. At least Kippy’s ain’t some yuppie bullshit place.”
Jimmy gulped some Budweiser. “Wasn’t that Stippo’s Liquor Mart, once upon a time?”
“Yeah. Bulger owned it. That’s where Pop got shot.”
“Never met the man,” Jimmy said, hoisting his brew, “but God rest his soul.... Your pop, not Bulger.”
“Hey, c’mon! Whitey was okay. He helped a lotta people in the neighborhood.”
To a Southie diehard like Patrick, that cold-blooded murderer was still the man.
The gaudy, carnival-like lottery broadcast came on the big screen over the bar and their task began, a hell of a job, going through Jimmy’s stack of tickets. Pat finally suggested they just check the Mega Ball numbers on the first pass.
The winning Mega Ball number was 3 and it took them about ten minutes to deal with all the tickets. Jimmy got the Mega Ball seven times and Patrick got it eleven. But, in almost all cases, no numbers on the left side of these Mega Ball tickets matched the other winning numbers.
Realizing the big payout had eluded them, they dug into the stack of tickets again, this time looking for a five-out-of-five match on the left side of the tickets – a possible million-dollar prize. But, as they worked their way through the stacks, they racked up only a dozen $9 wins. No five out of fives. Or even four out of fives. They got one three out of five with the Mega Ball number for $150.
After poring over the tickets for a few minutes, Patrick added it all up.
“You won $312,” he said.
Jimmy turned his palms up, empty, as he stared down at the ticket-strewn battlefield. “Three hundred and twelve stinkin’ bucks – on a two-grand bet?”
A sick feeling washed over him as he sat staring at his expensive pile of paper scraps.
“You caught some bad luck tonight, pal,” Patrick said.
“Yeah, well, I bought myself some with these fuckin’ tickets. I mean, you never play the lottery. Ever. You aren’t a dumb-ass like me.”
“You don’t deserve a beating for it.”
If a beating was all he got.
Eyeing the Bud Light wall clock, Jimmy slipped out of the booth.
“Time to go,” he said. Midnight was minutes away. “You don’t wanna have Deet’s goons catch up with me here. You’ll have to change the name of the joint like Stippo’s did.”
“Better go out the back way,” Pat said.
Patrick led Jimmy to the kitchen, past stacks of supplies to an old brick wall, then slid a cupboard aside, revealing a back door; before he let Jimmy out, he reached under his apron and pulled out a snub-nosed .357.
Pat said, “Take this.”
“Naw. You know I don’t do guns.”
“Tonight might be a good time to revise your Second Amendment thinking.”
“Not goin’ there.”
“Then you better go somewhere that ain’t Southie,” Pat cautioned. “In fact, get outa Boston, period, for a while anyway. Use some cash?”
“Naw! I’m good.” Another lie. Jimmy was flat broke.
“Here’s a hundred,” Pat said, stuffing the bills into Jimmy’s coat pocket. “No argument.”
Then Jimmy was running down the alley, glancing back just long enough to see Pat shaking his head, his expression indicating he was wondering the same thing as Jimmy.
Was this the last time he’d ever see his friend?
Copyright © 2021 Dave Thomas and Max Allan Collins