56 SPORTS ILLUSTRATED
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.
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 experi-
ences 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 Illustr ated, 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 privi-
leges. 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 with-
out 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 tick-
ets 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.
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 Sports1 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.” B E T T I NG AT
SING SING
