The Vibrant (and Still Illegal) Sports Gambling Scene That Exists Behind Bars

An inmate at Sing Sing Correctional Facility offers a glimpse into the weekly escape that NFL games bring.
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"Just go to NFL.com real quick," Red barks into the prison phone in the exercise yard. He’s standing in a caged dugout-like area, where 23 phones are attached to the outer brick wall of the building where Old Sparky electrocuted 614 people. Red’s likely not thinking about those lost lives, nor the two he took 25 years ago. He’s thinking about escaping. And for that he needs football stats and injury reports.

It’s Saturday afternoon, Week 11 of the NFL season, and I’m lapping the A Block yard at Sing Sing Correctional Facility, a maximum security prison in Ossining, N.Y. Crisp autumn air whips off the Hudson River as Mexicans, Dominicans and Albanian Eddy play pickup soccer on a slightly slanted open area of cracked pavement. By the bleachers two prisoners are going at it in a game of skully, flicking upturned bottle caps caked with soap around a board that’s been painted on the blacktop. Squat, flick. Squat, flick. Razor-wire-topped fences wrap the yard, which armed guards watch from towers 30 feet above. Most of us are from New York City’s five boroughs, just 30 miles down the river. Most have been in for decades, with decades more to go—doing football numbers, as they say, serving sentences as big as the numbers NFL linemen wear on their chests.

Red, who’s serving 40 years to life for a double homicide, blitzes across the yard. Joe-Joe hands him his fantasy football lineup, officially locking in his roster for the week. After a quick look, Red smiles and says, “Scumbag, you took Pittsburgh’s D.”

Then he turns to a group in state-issued green pants and sweatshirts and weighs in on Sunday’s matchups. “Dallas is a lock—Detroit’s QB is out,” he says. “Give me a ticket, Little Ant—I’m gonna crack that ass this week.”

It’s a typical scene in Sing Sing’s yard the night before NFL Sundays. Guys huddle around metal picnic tables, scoping out the tickets cupped in their hands. Dozens will eventually meander over to our table and pass off their ticket stubs to Little Ant.

By far the most popular form of sports betting in Sing Sing, prison parlay bets require bettors to pick correctly on four or more games in order to win. A runner for Mr. Li’s parlay-ticket operation, Little Ant’s a spunky 50-something Italian guy from Queens serving 14 years for a string of burglaries. He’s got cancer and a Top tobacco roll-up cigarette constantly dangling from his lips. “The most I ever sold was 110 tickets,” Ant tells me. “Every five, I get one [Top pouch]—so I made 22 pouches that week.”

In prison, cigarettes are the main currency. At the commissary a pack of Newports are $10.11, Top pouches are $3.27; three Tops equal a pack. Every two weeks prisoners can purchase up to 10 packs and nine pouches. So there’s money to be made.

“I like Arizona with the 13 [points over the 49ers. George] Kittle’s out,” says Joe-Joe, a black dude who is built like a linebacker.

“The over on the Baltimore game looks good,” says Puerto Rican Papo, who’s the runner for another bookie, Cono. Papo knows the odds. He’s been playing pick-four parlay tickets in prison every week during football season for 20 years. In all those years, he’s only hit twice.

“You and Mr. Li are fugazy bookmakers,” Carmine tells Little Ant. “You got Dallas minus-five. On Cono’s ticket, it’s minus-four.” Carmine’s a gangster from Howard Beach, Queens, who’s got John Gotti stories for days.

“F--- you, play his ticket then,” says Little Ant.

***

Believe it or not, placing bets was never illegal. It’s taking bets that always has been, but not anymore. A May 2018 Supreme Court decision overturned the 1992 federal law that effectively banned sports betting. Now, 16 states have legalized it, including New York.

Yet none of that applies in the joint. “An inmate shall not engage in any form of gambling, betting or wagering, or be in the possession of gambling paraphernalia,” reads the Standards of Inmate Behavior section of the New York State Codes, Rules and Regulations.

But most guards, who very well may bet on parlays and play in their own fantasy leagues, don’t sweat it. (They’re looking to bust more dangerous things, like drugs and weapons.) Plus, prisoners are smart about it, ripping off the parlay odds at the bottoms of the tickets. It’s hard for guards to prove that a list of games and spreads, or Red’s fantasy lineups, are gambling paraphernalia.

Red, 45, is Daniel Connelly. He has a bald head, crazy eyes and a red goatee that wraps a mouth with some gnarly teeth. He’s got an athlete’s body, though it’s broken down from too many winters powerlifting in prison-yard weight pits. In 1994, at 20, Red was hosting a house party that turned violent. Two young men were stabbed to death. Red was convicted of double homicide and got life in prison with the possibility of parole after 40 years.

Over the years, the wild redhead has had to continue showing his tough side. The full-tackle football league at Attica was a good outlet for his aggression. His team won three championships, even in the year when the opposing team’s middle linebacker, frustrated at Red’s team for playing too rough, shanked the center during a play. There’s no real football league in Sing Sing, so Red plays fantasy football, pinochle and dominoes instead.

***

In 2002, at age 24, I got locked up for murder and selling drugs, sentenced to 28 years to life. I came in with only a ninth-grade education, but in a creative writing workshop at Attica, taught by a volunteer English professor, I learned to be a writer. In ’13, I sent an essay to The Atlantic, and to my surprise, it was published. For a guy like me, who had been steadily losing in life up to that point, landing that story was like coming off the bench and catching a Hail Mary pass in the end zone. 

Doing journalism in the joint, though, requires walking a fine line, and this story was particularly tricky. “Some things you just shouldn’t write about,” an old-timer told me. “You know Donald Goines was killed because he revealed too much.” I didn’t know that. I did know that some Hell’s Angels beat down Hunter S. Thompson, the godfather of Gonzo journalism. I do get the feeling that prison administrators are in a huddle somewhere looking to get me out of the writing game.

John J. Lennon is a writer whose work has appeared in Esquire, The Atlantic and New York magazine. He hosts a podcast, "This is a Collect Call from Sing Sing," and is up for parole in 2029. (Courtesy of John J. Lennon)

John J. Lennon is a writer whose work has appeared in Esquire, The Atlantic and New York magazine. He hosts a podcast, "This is a Collect Call from Sing Sing," and is up for parole in 2029. (Courtesy of John J. Lennon)

But frankly, I’m more concerned about pissing off my peers. So this story is not an exposé about gambling in Sing Sing; it’s about our shared experiences and desires: to win, to escape. To cover my ass, though, I ran my ideas by a shot caller who carries a lot of clout with the prison population. I assured him I’d be discreet; no names. In the past he’s reminded me that even though I may be a journalist now, I’m still in prison. He gave me his O.K. (When Red heard this article would be in Sports Illustrated, though, he insisted I use his name. I’ve changed all the others.)

***

It’s Sunday afternoon, and the Fat Man and I are sitting at a picnic table on the so-called honor tier. Those of us who lock here have earned a few extra privileges. Cells have windows with Hudson River views. We get to use the phone, cook and play loud chess matches. Ravens QB Lamar Jackson is running all over Houston on the big flat screen at one end of the tier. Behind the TV, men are frying finger foods—mackerel, battered and dipped in corn flakes—on portable stoves. Fat Man became a forever football fan as a chubby nine-year-old watching Refrigerator Perry on the 1985 Bears. In another joint he ran a successful book. Now he’s at the end of his bid and has other priorities. But when Cono, his homeboy from the Bronx, came to him before the season with a bank of 200 packs and asked for help putting out a ticket, Fat Man agreed to train him and be his handicapper.

To keep track and confirm ticket winners without leaving a trail of incriminating evidence, Cono uses the model Fat Man came up with. He got the idea from the movie Red Heat, something about a big drug deal between two crews, a ripped $100 bill and a meet-up where runners show up with each side of the torn hundred. Teams are numbered; over/unders are lettered. The bettor circles the corresponding numbers and letters at the bottom of the ticket, tears it off and submits it to Papo with the cigarettes. Then Papo gets them to Cono who tracks all the bets on a master sheet.

It’s a weekly grind. Fat Man gets the line on Tuesday nights from the Fox Sports show Lock It In. He sits on his bed, watching the Clear Tech TV hanging off the locker door, then logs the spreads with his typewriter. He hands over about 130 tickets to Cono, who makes sure they’re circulating the yard by Wednesday night. While official spreads are set at half points to avoid ties, Fat Man tells me a prison parlay will always have whole numbers: a push, which goes to the bookie, kills the ticket. Fat Man also stays away from prime numbers, except seven.

For the bettor, it’s best to make just four picks, which pays 10 to 1. Five picks (15 to 1) and six picks (25 to 1) are very hard to hit. Fat Man tells me he’s hit a pick-six a few times, but he mostly plays pick-fours. Last year he hit eight times. This year, though, he’s mush, but he won three games today; in the Monday night game he’ll need the Chiefs to beat the Chargers by more than seven.

1. Each week, tickets like these circulate around the Sing Sing yard, listing the NFL matchups, with (a) point spreads and (b) over/unders marked by letters. 2. Bettors circle their picks—minimum four, max nine—at the bottom of their tickets, which are numbered. They tear off the stub and submit it with their stakes. 3. Cono's master sheet from Week 15 tracks each ticket, making it easy to identify winners, (c) like this one who correctly picked the Bucs, Patriots, Packers and Bills to cover. 4. This parlay didn't pay out: The Broncos, 10-point underdogs, lost to the Chiefs 23–3.

1. Each week, tickets like these circulate around the Sing Sing yard, listing the NFL matchups, with (a) point spreads and (b) over/unders marked by letters. 2. Bettors circle their picks—minimum four, max nine—at the bottom of their tickets, which are numbered. They tear off the stub and submit it with their stakes. 3. Cono's master sheet from Week 15 tracks each ticket, making it easy to identify winners, (c) like this one who correctly picked the Bucs, Patriots, Packers and Bills to cover. 4. This parlay didn't pay out: The Broncos, 10-point underdogs, lost to the Chiefs 23–3.

***

You could argue that fantasy football, the all-consuming game-within-a-game that has hooked millions of fans, helped pave the way for legalized sports betting in the U.S. For one, it never carried the stigma gambling does, and it’s so pervasive in mainstream culture that it was the basis of an FX sitcom, The League, and is played by everyone from singer John Legend, a man whose real life seems like an actual fantasy, to the inmates at Sing Sing.

Red’s hardly a walking sports almanac, and he makes no money for organizing, not at this small scale. He’s merely in it to win it and to escape the monotony of this place, like everyone else. At the beginning of the NFL season he and seven others put in five packs of Newports each. Red holds a draft, where the first pick goes to the person who plucks the lowest playing card from a deck. This year that was Red. With the first pick, he took Giants running back Saquon Barkley; Joe-Joe went with Steelers running back James Conner, Little Ant grabbed the Rams’ Todd Gurley, and so on until they all drafted their teams.

Without any access to the Internet—no real-time apps or organized fantasy sites—Red’s in charge of tallying the weekly stats himself. He gets them during the Sunday games by watching the fantasy news crawl on CBS’s broadcasts. Then he follows up by reading USA Today. To prepare for the next week, he’ll be glued to Fox Sports 1 or will listen to Anita Marks on ESPN Radio. If he needs any more information, he’ll phone a friend on the outside. Each week guys turn in their rosters and a pouch of Top tobacco; the highest scoring team for the week gets the eight pouches. At the end of the 16-week season, the first place team gets 20 packs of Newports, second place gets 12 and third gets eight. If a player in their lineup is benched or injured, he gives them zero points. “Here’s where the sneaky s--- comes in,” Red says. “The lowest scoring team gets first dibs at picking up two new players or a new defense.”

“Is that why you called Joe-Joe a scumbag last week?” I asked.

“Yeah, he picked up Pittsburgh’s D, which I just dropped the week before.”

Red sucks on a Top cigarette as he talks about the strange rooting interests you develop when you play two guys on opposing teams in the same week. It’s cold, and the ink in my pen seems to have dried up. I shake it and look up to find Red, who has the attention span of a puppy, has gone off to start a game of dominoes. “You know what I’m saying, Johnny,” he says. “If it’s a high-scoring game, you’re winning from both sides—it’s crazy!”

“Capicu, m------------,” yells Little Ant slamming his last domino on the table. He and Red won the game.

***

Fat Man’s ticket was a winner. K.C. came through and covered on Monday night, forcing Mr. Li to pay out 10 packs. Cono leaned on Fat Man’s cell bars sporting a cocky smile, telling him his take: 20 packs, 50 pouches. Nobody who put up a pack for a ticket won. Cono’s book this year hasn’t been hit for more than a pick-four all season. Neither has Mr. Li’s. As I mentioned before, anything more than a pick four is a sucker’s bet. A few pouch tickets did hit Cono this week though, and he had to pay out 40 Tops.

After Cono leaves, Fat Man tells me how sometimes jailhouse bookies do get hit hard. He remembers getting slammed one week for more than 250 packs when he was running a book. That’s more than two grand. Still, he came out the next week. “Customers need to see you get hit hard, pay out and come back out—it gives you cred and makes them want to keep playing,” he says. “The house always wins in the end.”

Fat Man tells me that his all-time favorite Super Bowl was in 1998. John Elway’s Broncos were taking on the Packers. Elway had previously taken Denver to the big game three times—all losses. But on the pivotal play, the quarterback ran the ball—crack, smack—and helicoptered into the end zone. “He was not gonna be denied that day,” Fat Man tells me, frying some chicken wings on the tier. “It’s a great get-knocked-down-but-stand-up story.”

I ask Fat Man his predictions for the Super Bowl. The game people would want to see, he says, is New England versus San Fran, the master (Tom Brady) versus his former student (Jimmy Garoppolo). But that obviously won’t be happening.

I tell Fat Man that I’ve had a man crush on Brady ever since Super Bowl LI, the comeback against Atlanta. “Tom Brady is the greatest winner in professional sports,” he tells me. “I can’t take nothing away from him.”

For that Super Bowl, in 2017, my tier had been the cleanest. So as a reward the strip of 88 cells on the fourth floor opened, and we marched down the stairs and into the auditorium, where we watched the game on the big screen and ate ice cream. By halftime the Patriots were down 28–3. I left early, crashing from sugar and bummed about losing the three packs I put down on New England. After being down like that, it’s beyond losing momentum—the spirit is broken. It’s a little like looking down a sentence of 28 years to life.

I got back to my cell in A Block, where Brady haters were on their bars talking all kinds of crap. Soon, the crowd quieted. I heard my Jamaican neighbor, who took Atlanta, say, “Damn, New England just scored. You can’t sleep on this m‑‑‑‑‑‑‑‑‑‑‑, Brady—the mon’s dangerous.”

I watched on the TV in my cell in awe as Brady led his team to the greatest Super Bowl comeback of all time. I couldn’t help but view it as a metaphor for my own life—trying to play a bigger game after being so down, seeking an inspiration to do something unbelievable . . . like, say, landing a feature in Sports Illustrated. From a cell.

***

Immersing myself in this story, I played numerous pick-four tickets and watched the games with intensity, taking note of all the FanDuel and DraftKings commercials. I asked guys for their locks. Red and Little Ant swore the Cowboys would be a lock against Buffalo on Thanksgiving. They weren’t. I tried to be contrarian, went with the unders with bad weather. Still, I lost every ticket.

It’s Wednesday afternoon, and the tickets for Week 14 are in the yard. The sky is blue, and the air is crisp. The river shimmers under the sun, which even makes the barbed wire sparkle a bit. It’s almost beautiful. The sound of a basketball pounding pavement complements the clinks and clanks of weights being lifted nearby in the pit. I’m listening to Red and Little Ant and Joe-Joe talk fantasy lineups. They’re talking about how Anita expects a good game out of Steelers receiver James Washington against Arizona. A guard walks by and asks what I’m working on. I tell him I’m taking readers to the fantasy sidelines in Sing Sing.

Red takes off to make a phone call; he wants to check the injury reports. One of our buddies, who did 30 years and is now out, is the one who goes on the internet for Red. When his phone rings and he hears that it’s a collect call from Sing Sing, he accepts, knowing the first words out of Red’s mouth will be: “Hey, go to NFL.com real quick. . . .”

The guy always obliges. After all, fantasy is the only way his friend can escape. 

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