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SPOTLIGHT
by Nina Wolpow ’10
Twenty-two years before two planes
crashed into Manhattan’s twin tow-
ers, Jack Pirozzolo ’83 arrived as a
Third Former at St. Paul’s School.
Pirozzolo worried little beyond his
next wrestling match, his responsi-
bilities as coxswain, or his fascination
with classics. He bonded with teach-
ers – John Buxton, Rich Davis, and
Chip Morgan among them – and
took pride in the talent of his peers.
“I was blissfully ignorant of pressure,”
Pirozzolo says.
His “ignorance” led him to Yale and,
after a stint in commercial real estate,
to the University of Chicago Law School.
He clerked for judges in Philadelphia
and Boston before landing a post-grad-
uation private practice job in Boston.
On a business trip in Kuala Lumpur on
September 11, 2001, Pirozzolo heard
what had happened in New York and
felt a call to action.
“I thought a lot about what I was doing
with my career,” he says. “I was happy,
but realized I wanted to do some public
service, to serve my country in some way.”
In the weeks that followed, Pirozzolo
applied to the U.S. Attorney’s Office
in Boston. His friends warned him the
decision could be a potential career
killer, but Pirozzolo was undeterred.
His instinct proved prophetic when the
U.S. Attorney’s Office hired him to prose-
cute securities cases. Later, U.S. Attorney
Carmen Ortiz asked Pirozzolo to sign
on as first assistant U.S. attorney, and
Pirozzolo’s jurisdiction widened from
white-collar prosecution to public cor-
ruption, violent crime, and instances
of terrorism. That is how the cases
of Boston mob boss James “Whitey”
Bulger and Boston Marathon bombing
suspect Dzhokhar Tsarnaev arrived in
Pirozzolo’s office.
Authorities apprehended Bulger, a
legendary Boston gangster indicted for
19 murders, in Santa Monica, Calif., on
June 22, 2011. Pirozzolo supervised the
prosecution and served as lead prosecu-
tor of Bulger’s girlfriend, Catherine Greig,
who was convicted in March 2012 of har-
boring the fugitive Bulger for 16 years.
A federal judge sentenced Greig to eight
years in federal prison.
Jack Pirozzolo ’83:
Cool Under Pressure
