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AS A YOUNG U.S. attorney in Manhattan, New York City, Rudy Giuliani was considered hard-hitting and on his way to greater things. In 1986, Giuliani became the U.S. attorney for the southern district of New York. Giuliani decided that his mission in life was to go after white-collar criminals on Wall Street in a crackdown unlike any the financial center had ever seen. While the insider-trading probe was already in progress when Giuliani came on board, he became its motivating force.

His first target was Michael Milken and his junk bond kingdom, Drexel Burnham Lambert (DBL). Giuliani's first arrest came in May 1986 with the apprehension of DBL investment broker Dennis Levine. Giuliani then went after Ivan Boesky who admitted he had used inside information provided by Levine and agreed to pay $100 million in fines. Giuliani and his team convinced Boesky to wear a “wire” to help bring down 10 other traders at DBL who eventually pleaded guilty to securities fraud. It was later reported that Giuliani had allowed Boesky to take a $50 million tax write-off on his $100 million fine. Giuliani's 4,152 convictions also encompassed ordinary criminals, including drug dealers, and members of organized-crime families.

Giuliani's treatment of Richard Wighton and Timothy Tabor of Kidder, Peabody, and Company and Robert Freeman of Goldman, Sachs was reportedly very different than those involved in the DBL arrests. People who are accused of white-collar crimes are generally allowed to surrender themselves. However, Giuliani chose to embarrass these individuals by having federal marshals arrest and handcuff them. Wighton, for instance, was arrested at his office, where he was led away in tears. This behavior was also markedly different from Giuliani's arrest of members of the Gambino crime family. Paul Castellano was picked up at home, never hand-cuffed, and was allowed to buy a candy bar on his way to the police station.

After losing a 1989 campaign for mayor of New York, Giuliani was successful in winning the office in 1993, focusing his campaign on improving the quality of life for citizens of the nation's largest city by improving education and curtailing crime. Some critics argued that the mayor treated a number of groups with no more respect than he showed criminals. Giuliani's record on civil liberties and civil rights was decidedly abysmal. Giuliani supporters, however, pointed to the mayor's record on fighting crime that had resulted in the Federal Bureau of Investigation's (FBI) naming New York City as the safest large city in the country. In addition to safer and cleaner streets, Giuliani reduced welfare rolls and taxes, increased jobs in the private sector, and revived New York City's nightlife.

Ruth Messinger, Rudy Giuliani's Democratic challenger in the 1993 campaign, had pointed out with much truth that Giuliani had no real plan for his second term. He did promise to spend $64 million more of the city's money to hire 40,000 new police officers. Perhaps the most ludicrous of Giuliani's actions during his second term was his campaign to make New Yorkers more polite. Instead of focusing on hardened criminals, the mayor instructed his police officers to go after jaywalkers, litterbugs, the homeless, “irresponsible” taxi drivers, “dangerous” bicyclists, food vendors, street artists, and owners of shrieking car alarms. A number of friends and allies turned on Giuliani when he laughed at recommendations from his own 28-member taskforce on Police-Community Relations. When things started to unravel in his second term, his political enemies, including liberals, Harlem politicos, educators, and civil libertarians also turned on Giuliani with a vengeance. The mayor's approval rating dropped an amazing 21 percent.

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