93insidestory· books
AUGUST 2019swers. Touting his giving, trusting na-
ture as the reason for his success makes
it easier for the listener to believe that
it was this same nature that landed him
in prison. It lends him credibility when
he then goes out of his way to criticise
someone, such as Bharara or Kumar.
While at Harvard, soon after Gupta
grew comfortable with speaking up in
class, he began to be ignored by his pro-
fessor, who told him that his complex
ideas were confusing the classroom.
Finding it unfair that he was being
disadvantaged for his advanced under-
standing, Gupta proposed to the profes-
sor, “Grade me on only my final exams
and I’ll stay quiet in class.” He was one
of two students who got an “Excellent”
grade in the subject.
At IIT Delhi, Gupta was rejected in
the first round of ITC’s group inter-
views. He felt “galvanised by the sense
of unfairness,” believing he was a wor-
thy candidate, and told the interviewer,
“Excuse me, sir, but I think you are
making a mistake.” The move worked,
as it did two years later, when he was
initially rejected by McKinsey. This
time, a professor found him troubled
in class. He sent McKinsey a three-
sentence recommendation, urging them
to interview Gupta again.
Any respect Gupta may have had
for Rajaratnam as a fellow immigrant
and successful businessman perhaps
stemmed from a genuine appreciation
for Rajaratnam navigating challenges in
a seemingly unfair, often alien, world.
It may even have fit into his idea of a
meritocratic worldview, where the per-
son who best uses whatever he can get
should succeed the most.
Gupta has clarified in multiple inter-
views what his memoir is not—that it
is not an attempt to clear his name in
the court of public opinion, but merely
to tell his side of the story. By talking
about his professional life, he hopes that
readers would learn from his experienc-
es.However,thestoryofhislongcareer
is sandwiched between Gupta’s experi-
ence of the trial and prison, in which
he presents himself as a maligned inno-
cent. As Deb put it, “He has had seven
years to spin a story.”
The first time Gupta was sent to soli-
tary confinement, it was as punishment
for bending down to tie his shoelaces
just as a correctional officer was com-
mencing his check. “It doesn’t take
much at all,” he writes. “A moment of
carelessness. A misjudgement. Bad
timing.” The phrases have the striking
effect of doubling up as an encapsula-
tion of Gupta’s entire defence, in the
book and in the media. However, this
argument does not apply as neatly to his
crime, leaving one to wonder about the
not-so-thin line between understand-
able human error and a deliberate an-
tipathy for rules and values.
Gupta met his difficulties in prison
with stoicism, wanting to emulate his
father, who contracted the tuberculosis
that would end his life while he was
jailed by the British. While still in Cal-
cutta, Ashwini Kumar Gupta had pri-
vately tutored college students. One day,
an invigilator at a Calcutta University
examination caught him in dark glasses,
impersonating one of his students to
help him pass the exam, in exchange for
money that would go to the revolution-
ary cause. Here was another admira-
ble man with a blameless reputation,
marred by a single infraction, perhaps
committed with the belief that it was
the right thing to do.
This dichotomy in character and
crime, as Rakoff said, “presented the
fundamental problem of this sentence,
for Mr Gupta’s personal history and
characteristics starkly contrast with
the nature and circumstances of his
crimes.” Proving a motive was never a
necessary legal element of Gupta’s of-
fence, but the question lingered: why
would the poised, bespectacled man
on stage at the Regency ballroom get
caughtupinsucha typicallyavariciousact? In his sentencing order, Rakoff per-
mitted himself to speculate:Having finished his spectacular
career at McKinsey in 2007, Gupta,
for all his charitable endeavors, may
have felt frustrated in not finding
new business worlds to conquer; and
Rajaratnam, a clever cultivator of
persons with information, repeatedly
held out prospects of exciting new
international business opportunities
that Rajaratnam would help fund but
that Gupta would lead. There is also
in some of the information presented
to the court under seal an implicit
suggestion that, after so many years
of assuming the role of father to all,
Gupta may have longed to escape
the straightjacket of overwhelm-
ing responsibility, and had begun to
loosen his self-restraint in ways that
clouded his judgment. But whatever
was operating in the recesses of his
brain, there is no doubt that Gupta,
though not immediately profiting
from tipping Rajaratnam, viewed it as
an avenue to future benefits, oppor-
tunities, and even excitement. Thus,
by any measure, Gupta’s criminal acts
represented the very antithesis of the
values he had previously embodied.At the launch, Trehan reflected on a
portion of the memoir where, having
lost everything he once held so dear,
particularly his reputation among his
friends and colleagues, Gupta realises
that one is only unhappy as long as one
remains attached to such concepts. De-
tachment from reputation is liberating.
“How is that possible?” she asked. “Isn’t
reputation your conscience?”
“I think, to me, they are two very dif-
ferent things,” Gupta said. “Reputation is
other people’s view of you, whereas con-
science is your own.” He said letting go
of reputational concerns was liberating
“because I don’t have to conform to some
viewjustbecauseotherpeoplewant
meto.Thatdoesn’tmeanthatI don’t
careaboutdoingtherightthings.That
doesn’tmeanthatI wanttoknowingly
commita crime.ThatjustmeansI want
todotherightthingandI don’tcare
whetherit createsa goodreputation,a
so-soreputationorevena badone—as
longasI’mdoingtherightthing.” sBy assigning broad dates to his discovery of the
Voyager fiasco, the book maintains a semblance of
internal consistency. Gupta is able to freely move
back and forth in the narrative, explaining one call as
friendly, but the subsequent ones as belaboured.