state for a Black man. And listen, I’m not Drake
black. I’m, like, Shaka Zulu black. You know
what I’m saying?’’ Three of the other defendants
who used these stolen miles got real time. ‘‘One
guy got up there trying to explain all kinds of
[expletive] and making excuses. That’s the wrong
thing to do. But he didn’t have anyone to tell him,
because that’s just your natural instinct when you
get in front of somebody. ‘Judge, wait a minute,
man. I ain’t do nothing. Come on now. Hold on,
man. You know, I’m just out here’ — slam.’’ T h a t
guy was sentenced to two and a half years.
‘‘My judge saw me diff erently,’’ he said. ‘‘She’s
like, ‘Based on what I’ve read about you, you
shouldn’t even be in here.’ ’’ In the sentencing
hearing, Judge Jane Boyle said aloud, ‘‘I wonder
if he even should have been prosecuted.’’ Then
she said, ‘‘I’d like to give you six months pro-
bation, but I can’t.’’ Then she turned to a court
offi cer for clarifi cation. ‘‘Do I have to give him,’’
she asked, ‘‘a year probation?’’ Informed that the
guidelines required at least one year of probation,
she imposed exactly that. ‘‘That’s because she was
able to read my story,’’ he said.
Much of Paperny’s advice comes from his
own attempts to avoid prison when the Ponzi
scheme he enabled collapsed. After being
nabbed, he fi gured he would outsmart the feds
with a series of artful dodges and deceptions.
In the midst of constructing this web of lies,
Paperny insisted that he take a lie- detector
test. ‘‘I immediately Googled for information
on polygraph examinations,’’ Paperny writes in
his self- published confessional, ‘‘Lessons From
Prison.’’ He found a $350 online course, which
taught him all the ‘‘ostensibly proven tech-
niques’’ to evade the lie detector. ‘‘By tighten-
ing my sphincter when answering questions,’’
he wrote, ‘‘I supposedly could manipulate the
machine’s fi ndings of truth to suit my purpose.’’
And yet even though he ‘‘practiced so fervently’’
and then ‘‘squeezed my innards when appro-
priate,’’ the polygraph administrator informed
him afterward that ‘‘the machine indicated with
an accuracy measurement of better than 99.99
percent’’ that he was lying.
‘‘Justin,’’ he added, ‘‘you’re going to prison.’’
Once that reality set in, Paperny prepared the
same way everyone does, and how his clients still
do — Googling ‘‘what happens when you go to
prison?’’ He learned a jumble of information, but
then the day came. Paperny reported to the Taft
federal prison camp in California, changing his
street clothes for a prison outfi t. He quickly dis-
covered that there are lots of rules in prison that
Quora doesn’t have the answers to, and routines
you have to discover by yourself.
Soon enough, he met people and was told
about people. There was a guy known as Dopey,
another known as Road Runner. He heard about
a mysterious fi gure named the Kingpin, who
had served the longest and hardest time. And
then there was Drew, the hustler on his fl oor
who lured Paperny into accepting a contraband
mattress, a dangerous fi rst step because getting
caught by the guards doing anything shady can
easily win you an extended sentence. It was all
dizzying, so Paperny decided to lie low and do
what most inmates do — exercise and try to stay
out of trouble.
After a few days, the Kingpin was in the TV
room and introduced himself. His name was
Michael Santos, and he was busted for dealing
in 1987, at the height of President Ronald Rea-
gan’s war on drugs. For a fi rst off ense, at age 23,
Santos was sent to federal prison for 45 years.
Whatever Paperny might have been expecting
— a battle- scarred lifer, a guy who could turn a
Bic pen into a shiv — Santos wasn’t it. Instead,
he was a self- educated man whose years of
reading transformed him into something far
beyond your typical jailhouse lawyer — more
of a jailhouse philosopher, concerned with the
metaphysics of confi nement.
Santos wanted to know if Paperny had ever
read ‘‘The Divine Comedy.’’ ‘‘In Dante’s epic
poem,’’ he said, ‘‘Virgil off ered Dante a way out
of the forest.’’ Santos encouraged him not to
worry so much about the softball league or the
card games or all the other time- wasters avail-
able to prisoners who instinctively believe that
their years behind bars are meant to be useless.
He encouraged Paperny to read Aristotle and to
‘‘know thyself.’’ He told him he should really read
Sun Tzu, too, and learn to ‘‘know thy enemy.’’
Like any sane convict, Paperny thought: You’re
kidding me. That’s the wisdom of the centuries?
Are you serious? Paperny wondered what the
point was of all this Reader’s Digest philoso-
phy, but he found the books interesting. Who,he wondered, was his ‘‘enemy’’? Maybe, Santos
told Paperny, the enemy is not a who. ‘‘Maybe it’s
a what,’’ he said. ‘‘Maybe it’s a prison term. Maybe
it’s an unfulfi lling career that leads you to misery,
or to bad decisions that land you in prison.’’
At the time, Paperny was dealing with a lot
of practical prison problems. He was working
in the kitchen, under the thumb of an aggres-
sive inmate who traffi cked liberally in Holocaust
denial. And then there was Santos, slowly teach-
ing him to look past the offi ce politics of prison
and try to see his confi nement as a bounty, a gift
of years to prepare for what comes next. Think
of prison as a business- planning session, Santos
told him — he’d been thinking that way for years.
He’d already written several books, about get-
ting through prison. Paperny was due to get out
a lot earlier than he was, Santos pointed out, so
maybe he could get a jump on the obvious busi-
ness idea — advising incoming felons on how
best to handle a future of prison. When Paperny
got out in 2009, he founded the business, with
Santos joining on his release four years later.
Today, Paperny and Santos are business
partners, co- founders of White Collar Advice
and another business called Prison Professors,
which is Santos’s attempt to make their services
and philosophy available to anyone, not just the
white- collar felons who can aff ord their fees.
(Paperny told me those fees range from a few
thousand dollars into the six fi gures.) Santos’s
intention, long before he got out, was always
much bigger than consulting with white- collar
criminals, whom he described as merely the
‘‘consumer side’’ of the business.
‘‘It’s way more important to me to help the
million people that are in prison who keep recid-
ivating,’’ he said. To that end, the other side of
the business seeks to recreate for thousands of
prisoners a certain encounter Paperny had not
long after meeting Santos. ‘‘When I went in, I
was a fat, miserable, self- loathing white- collar
defendant blaming everyone but myself,’’ Paper-
ny said, ‘‘and adjusted to prison like you do, com-
plaining and exercising seven, eight hours a day.’’
Then the Taft prison camp philosopher sidled
up to him at the gym one day. ‘‘And Santos said
to me, kind of joking, like, ‘Hey, bud, how much
are people going to pay you to do those pull-ups
when you get out?’ AndThe New York Times Magazine 27(Continued on Page 47)‘ONE GUY GOT UP THERE TRYING TO EXPLAIN
ALL KINDS OF [EXP
LETIVE] AND MAKING
EXCUSES. THAT’S THE WRONG THING TO DO.’