With a Bullet

With Chaykin as his partner, Udolf tackled the case that would be his most famous as a prosecutor: the extortion and racketeering case against Hialeah Mayor Raul Martinez. For two years, the two prosecutors collaborated with a team of FBI agents and undercover operatives, building a paper trail and witness list that would demonstrate to a jury that Martinez received cash loans and property from people in exchange for zoning favors.

The investigation was a sprawling one, and the evidence against Martinez was so subtle, so nuanced, that it would test a prosecutor's adeptness at simplifying and framing the subject so it was comprehensible to a jury of laypeople. The pair was also under pressure to keep the case in a political vacuum — an impossible task considering that Martinez supporters rallied outside the courtroom. They were certain the case had been cooked up by Udolf's boss, U.S. Attorney Dexter Lehtinen, whose wife, Ileana Ros-Lehtinen, sought the same congressional seat as Martinez.

Udolf and Chaykin won a conviction against Martinez only to have the conviction reversed by an appeals court. The second trial ended in a hung jury, and after the third seemed headed in the same direction, prosecutors dropped their charges.

That case had occupied Udolf for the better part of a decade, and his failure to get a conviction dealt a blow to the high ideals that were the basis of his career in justice, though it couldn't discourage him entirely. "They're important pieces of work for the government to do," Udolf says of public-corruption cases. "Because the principle deterrent to public officials corrupting their offices is the knowledge that there will be a thorough investigation and prosecution." Martinez has been largely scandal-free since, and he is currently running for U.S. Congress. He did not return calls seeking an interview for this article.

Not long after the Martinez verdict was overturned, Udolf's daughter, Hayley, was born, an event that Udolf says brought new financial pressures and the temptation to parlay the name he'd built for himself in the public sector into private practice. But before he could make that move, history — in the form of Kenneth Starr — intervened.

In June 1997, Udolf and his wife were driving to Miami International Airport when a news report came on the radio. Investigators for the Office of the Independent Counsel, Kenneth Starr, had begun questioning members of the Arkansas Highway Patrol who handled the security detail of then-Gov. Bill Clinton as to extramarital dalliances. Already, commentators were asking what these concerns had to do with the original basis for the investigation: Bill and Hillary Clinton's Whitewater land deal. It was beginning to look like Starr's team was straying out of legal bounds in making its case against the president.

Udolf turned to his wife and said, "I hope I didn't just make a mistake." The month before, he had been recruited to join the Starr team, and at that moment, she was dropping him off for his flight to Washington, D.C.

In his New Times interview, Udolf said he had expressed concerns about joining an investigation that appeared led by partisan Republicans. "I said to them, 'You know, I'm a Democrat, and there's not a great perception out there that you guys are looking to do the right thing here,'" Udolf recalls. "They said, 'We know that [you're a Democrat], but we also know that you prosecuted Democrats and that you're pretty open-minded when it comes to that.' " Conversely, Starr's willingness to hire a Democrat helped persuade Udolf that these investigators weren't political errand boys, as they'd been cast in the media.

Besides, Udolf was thrilled to get a shot at making history. "I was a public-corruption prosecutor," he explains. "And this was the mother of all cases." Rarely, he notes, does a prosecutor get the chance to investigate a sitting American president.

It would go down as one of the few episodes in Udolf's career that he regrets, perhaps not for any single decision he made so much as being associated with the case at all.

Not surprisingly, his rivals in the race for sheriff have made a habit of citing his involvement with the Starr investigation. One campaign flier, circulated anonymously, admonishes voters, "Don't forget Whitewater."

Udolf naturally feels obligated to put his role in the case into context. "For the first six months or so, I was investigating allegations that I would consider to be in traditional areas of corruption," Udolf says. That is, he investigated the tax records of Webster Hubbell, a lawyer who was a friend of the Clintons' in Arkansas and became a powerful figure in the U.S. Justice Department. At the time, there was suspicion that the windfall of consulting work Hubbell received after his resignation was an illegal way to reward the administration for political favors.

As that inquiry stalled, Udolf and others on Starr's team shifted their focus to a new lead: a White House intern, Monica Lewinsky, who had told her friend Linda Tripp that she had an affair with Clinton and was prepared to lie about it under oath, per the president's request. History remembers Udolf as an ambivalent collaborator in Starr's effort to recruit Tripp and Lewinsky. In the book A Vast Conspiracy by Jeffrey Toobin, Udolf is quoted as telling another prosecutor, "That woman [Tripp] is a fucking cunt. If you want to get in bed with that bitch, you're going to pay for it eventually."