54 SPORTS ILLUSTRATED
Just go to NFL.com
real quick,
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 25years ago. He’s
thinking about escaping. And for that he needs
football stats and injury reports.
It’s Saturday afternoon, Week11 of the NFL sea-
son, 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 Alba-
nian 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 black-
top. Squat, flick. Squat, flick. Razor-wire-topped
fences wrap the yard, which armed guards watch
from towers 30feet above. Most of us are from
NewYork City’s five boroughs, just 30miles 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 110tickets,” Ant tells me. “Every five, I get
one [Top pouch]—so I made 22pouches 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 PuertoRican 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,” Car-
mine 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
Red barks into the prison phone in the exercise yard.
J A I L H O U S E
ACTION
To keep track of
his bookmaking
operation, Cono
uses a coded
system and
meticulously
logs each bet. In
Week 15, only
four of 38 parlay
tickets were
winners.
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.
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.
Cono’s master
sheet tracks
each ticket,
making it easy to
identify winners,
(c) like this one
who correctly
picked the Bucs,
Patriots, Packers
and Bills to cover.
This parlay didn’t
pay out: The
Broncos, 10-point
underdogs, lost to
the Chiefs 23–3.
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