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In a few cases, his arrests of alleged white-collar criminals at their workplaces with charges later dropped or lessened, sparked controversy, and damaged the reputations of the alleged "perps".He claimed veteran stock trader Richard Wigton, of Kidder, Peabody & Co., was guilty of insider trading; in February 1987 he had officers handcuff Wigton and march him through the company's trading floor, with Wigton in tears.

In 2014, it was revealed by former Sicilian Mafia member and informant, Rosario Naimo, that Salvatore Riina, a notorious Sicilian Mafia leader, had ordered a murder contract on Giuliani during the mid-1980s.

As a federal prosecutor, Giuliani was credited with bringing the "perp walk", parading of suspects in front of the previously alerted media, into common use as a prosecutorial tool.

Giuliani's critics claimed that he arranged for people to be arrested, then dropped charges for lack of evidence on high-profile cases rather than going to trial.

In the Mafia Commission Trial (February 25, 1985 – November 19, 1986), Giuliani indicted eleven organized crime figures, including the heads of New York's so-called "Five Families", under the Racketeer Influenced and Corrupt Organizations Act (RICO) on charges including extortion, labor racketeering, and murder for hire.

Time magazine called this "Case of Cases" possibly "the most significant assault on the infrastructure of organized crime since the high command of the Chicago Mafia was swept away in 1943", and quoted Giuliani's stated intention: "Our approach is to wipe out the five families."Gambino crime family boss Paul Castellano evaded conviction as he was murdered on December 16, 1985, alongside his underboss, Thomas Bilotti, the murders were orchestrated by up-and-coming mobster John Gotti who took over the Gambino family and would later be sentenced to life without parole in 1992 for the murder and numerous other crimes.

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