The guardian, continued
Chertoff already displayed many of the traits touted by supporters when he was a Harvard Law student 30 years ago. He had barely arrived at HLS when his fierce advocacy and intensity first drew notice. He engaged Professor Duncan Kennedy in a running argument for two days during class, sparring with him over judicial enforcement of the District of Columbia's rent-control law. "I was arguing for what we call judicial restraint," Chertoff said in a recent interview with the Bulletin. "He was arguing for activism."
Kennedy has no recollection of the exchange, but it stuck in the mind of classmate Scott Turow, who later described Chertoff as the brightest student in the section. (Turow is said to have used Chertoff as the basis for at least one of his composite characters in his book "One L," although he declines to say which characters are based on which students.) "Chertoff was not reluctant to debate with anybody," remembered Turow. "He was self-confident, assertive, but never obnoxious."
After graduation, Chertoff clerked for Murray Gurfein '30, a judge on the U.S. Court of Appeals for the Second Circuit, who regaled him with tales from his own days of prosecuting mobsters under then New York District Attorney Thomas Dewey in the 1930s.
"I realized that the prospect of doing a case in court was the most exciting thing you could do as a lawyer, plus I was interested in public service," said Chertoff. "The best place to do that was in a prosecutor's office."
After a U.S. Supreme Court clerkship with Justice William J. Brennan Jr. '31 and a few years as an associate at Latham & Watkins, Chertoff landed in the office of another prosecutor with his eye on organized crime, Rudolph Giuliani, then the U.S. attorney for the Southern District of New York. Giuliani assigned the 32-year-old Chertoff the role of prosecuting the heads of New York's top mob families. They employed what was then a novel legal theory, charging and trying a major case under the federal racketeering statute and proving that the heads of the families had conspired as part of an illegal racketeering enterprise called the "Commission."
The threat of violence hung over the three-month trial from the start, says fellow prosecutor John F. Savarese '81. Shortly before the trial began, one of the defendants, Paul Castellano, was gunned down outside a Manhattan steakhouse.
Savarese recalled Chertoff's "quiet authority and mastery of the facts and sincerity that [came] through and really connected with the jury." All eight defendants in the case were convicted. (One of them, Anthony "Fat Tony" Salerno, later quipped that Chertoff owed him thanks for landing him his next job, as first assistant U.S. attorney in New Jersey.)
Chertoff's reputation as a relentless prosecutor grew with each case. The American Lawyer magazine noted his "Gatling gunslinger" style of questioning. The Weekly Standard said of his interrogations, "[He] can make smart people look stupid."
In 1990, President George H.W. Bush picked Chertoff to be U.S. attorney for New Jersey, and, in the state where he was born and raised, Chertoff often outshined his former colleagues across the river in New York. He prosecuted several mayors on corruption charges and handled the made-for-tabloid case against Chief Justice of New York Sol Wachtler for threatening to kidnap his former lover's daughter.