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With a Bullet

Former Hialeah Mayor Raul Martinez was one of Udolf's targets as a prosecutor
Tara Nieuwesteeg

Last September, Bruce Udolf and his wife, Sheryl, were in the living room of their Southwest Ranches home watching the news. A report came on about disgraced Broward County Sheriff Ken Jenne, who had just resigned after entering a guilty plea to mail fraud and tax evasion based on pocketing some $86,000 in illegal payments.

In the annals of Broward County politics, Jenne's was an epic collapse. Before taking over as sheriff in 1998, he'd represented the region for 18 years in the state legislature. His career in public service had started in the '70s — as a state prosecutor who relished busting crooked politicians. This had been Udolf's calling too. In the '90s, he was South Florida's top federal prosecutor when it came to public corruption cases. In 1997, he left for an ill-fated stint on Kenneth Starr's legal team, investigating President Bill Clinton. A few months later, Udolf gave up crime-fighting altogether and became a criminal defense attorney.

Only he'd never quite lost his prosecutorial sensibilities. When the news segment ended, the now-56-year-old Udolf unleashed a diatribe, right there in the living room, about Jenne and how the next sheriff ought to clear out the department cronies and instill some accountability in the ranks. When he finished, his wife said, "You should run for the office." She was joking.

Udolf wasn't. He told her he'd already made up his mind to do exactly that.

In the years since leaving the Justice Department, Udolf had made no secret of his interest in an appointment to U.S. attorney. But with George W. Bush in the White House, a Democrat like Udolf had no chance. Cleaning up the Broward County Sheriff's Office may have seemed like the next best option — or at least one that was open to him.

But running for Broward sheriff is not the kind of endeavor one embarks upon casually. The job comes with a $700 million budget and 6,000 employees. It is the largest accredited sheriff's department in the nation, functioning as the police force and fire rescue in more than a dozen cities and towns as well as all the unincorporated sections of the county. Its deputies staff the courts and the jails. The Broward County sheriff ranks among the most powerful public officials in the state.

After Jenne's resignation, Gov. Charlie Crist appointed a fellow Republican, Al Lamberti, to the post. But given the county's majority Democratic registration as well as high voter enthusiasm, a Democrat stands an excellent chance of winning the general election. That's why the primary election Tuesday (August 26) looms large. Five candidates will be on the ballot, each of whom comes with at least one major question mark.

In Udolf's case, the central question is why a wealthy defense attorney would seek an extremely demanding, intensely public job that pays $170,000 — a fraction of what he makes in the private sector? That very question haunted Jenne ten years ago.

Udolf himself struggles to explain exactly what prompted his candidacy. During a recent lunch hour, Udolf saw an acquaintance who had learned about his candidacy from seeing a "Udolf for Sheriff" sign. "I know," he told the woman. "I should have my head examined."

Udolf had agreed to give New Times an interview about his desire to become sheriff. But on the evening of July 30, on his way to meet a reporter, he received a call informing him that his best friend, Steve Chaykin, had fallen to his death at age 56 while on a hiking trip with his wife. Udolf was devastated. He and Chaykin had worked together as prosecutors in the early 1990s and had remained best friends even after they both left the public sector.

The following week, after Udolf delivered the closing eulogy at Chaykin's funeral, he recalled how he'd sought out his friend in the days before he struck out on a bid for Broward sheriff. "He was one of the few people," Udolf says, "who didn't think I was crazy."


In the days before he learned of Chaykin's death, Udolf's biggest concern was the health of his pinkie. While walking the ample grounds of his Southwest Ranches home with his wife and 12-year-old daughter, the family's two hunting dogs set upon the family cat. They might have torn the cat in two had Udolf not dived between them. In doing so, he bent the pinkie on his left hand. He received a splint and the news that it would be crooked forever.

The problem: Udolf is a serious bass player. For most of his life, that avocation has been a refuge from the gravely serious business of practicing law. A native of Long Island, New York, Udolf played in bands of every genre after graduating from Hofstra University, where his father was a professor. Rock 'n' roll was the hobby, though, not the career. He eventually enrolled in law school at Emory University in Atlanta and then found a position as an assistant district attorney in the northeastern Georgia town of Gainesville.

By his third year, the district attorney who had hired him retired and endorsed Udolf as successor. At just 29 years old, Udolf won the election. Although he would be defeated in his bid for a second term, Udolf's résumé landed him a job at the U.S. Attorney's Office in Miami, where he advanced quickly from major crimes to narcotics. In 1988, he landed an assignment in the public-corruption unit, where he would encounter another fast riser, Steven Chaykin.

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."

Despite these reservations, Udolf zealously worked Lewinsky, the witness Tripp delivered. On February 2, in a conference call with Lewinsky's attorney, William Ginsburg, Udolf negotiated the terms of a statement Lewinsky would provide in exchange for immunity from obstruction-of-justice charges. At its conclusion, he remarked, "I think we have a deal."

As Udolf tells it today, that was his sole option. "If someone comes forward with evidence that a person is trying to get them to lie under oath, that merits scrutiny," he says. "The only direct evidence of that could only come from Monica Lewinsky. She would have been an essential witness, the only witness."

The hardliners in Starr's office disagreed. They lobbied Starr to veto the verbal agreement, then give them more time to press Lewinsky for a better statement, and that's what he did. "They retracted the immunity agreement the moment it was signed, which I found offensive," Udolf recalls. "As an attorney, I don't have to put something in writing. If I gave you my word, that's it."

He was coming to feel that the office he'd joined wanted "an extended grand jury investigation, which could divide the country. It's abuse of the grand jury to use it for any other purpose than to legitimately investigate criminal conduct, not embarrass people politically and build a case for impeachment."

As if being second-guessed by Starr weren't enough, Clinton aide Sidney Blumenthal had resolved to give Udolf a lesson in humility. According to Toobin's book, it was Blumenthal who dredged up embarrassing episodes from the histories of Whitewater prosecutors, then fed them to reporters. In Udolf's case, that effort produced articles about the civil suit in Georgia in which his office was found to have mistreated a suspect in a drug arrest — a case that, not surprisingly, has resurfaced in the sheriff's race.

After eight months working with Starr's team, Udolf took a break to visit his family and to consider whether he should soldier on or resign. "I never made a major life decision without talking to Steve," says Udolf, and this was no different. Since he wanted Chaykin's advice not just as a friend but as a lawyer, he offered a dollar bill for legal services. Chaykin told him, "Figure out what is right, and do that."

Udolf exclaimed, "That's it?"

Chaykin told him, "Well, you only paid me a dollar."

Still, it was the nudge Udolf needed to act on his impulse to abandon the investigation, what he now calls "probably the meanest, nastiest political debacle this country has ever seen."


Having returned home to his family, Udolf and his wife had a frank discussion about his career, which for all the hours spent away from home had not made the couple wealthy, at least by lawyer standards. Udolf remembers his wife making a candid, convincing case: "You've had a good run, done good work, and now it's time for you to make some money for us."

With that, he moved into private practice, settling at the firm Berger Singerman to specialize in criminal defense work for those accused of white-collar crimes, as well as complex civil litigation. The work is lucrative, but for an attorney who had worked cases on a national stage, it's also decidedly low-profile.

If the Martinez case had tested Udolf's ability to keep politics at bay during an investigation, joining the case against Clinton taught him that he couldn't always trust his fellow prosecutors to do the same. The experience may prove valuable if, as sheriff, Udolf's own investigators bring a case to him that has political consequences.

Though Udolf moved decisively into private practice, he couldn't quite restrain his lust for cases that were high on profile, low on pay. One of his first was the defense of David Farrall, a white FBI agent accused of drunken-driving manslaughter in a head-on collision that killed two young men of Jamaican descent who were returning home from choir practice. Farrall was leaving a bar. Since the Florida Highway Patrol botched the investigation, there was no definitive way to know which of the cars was driving the wrong way on Interstate 95 and deserved blame for the accident.

The trial was racially charged, especially after patrol officers initially blamed the brothers for causing the accident only to revise their conclusion and charge Farrall. It received intense media scrutiny. In petitioning for a change of venue, Udolf produced a news analysis that ranked it South Florida's third-most-covered story of 2001, behind the controversy over uncounted votes in the presidential election and the Elián González custody battle.

To Udolf, the media coverage was slanted against his client and failed to accurately render the ambiguities of the case. As the media turned up the heat, Udolf's efforts intensified. Farrall lost his job, his fiancée, and all his savings. "David, all he ever wanted to be in his whole life was an FBI agent," Udolf says of Farrall, whose mother was a secretary to J. Edgar Hoover. "I felt this guy didn't have a friend in the world. All he had was me, and I wanted to do what I could for him."

Udolf won acquittal for his client on the charges of manslaughter. Farrall was convicted only of DUI, for which he received the maximum 90 days in jail, still a far cry from the 30 years a conviction might have brought.


The campaign for Broward sheriff is not a hugely expensive one, at least not compared to campaigns for congress or governor. No Democratic contenders have raised more than $200,000. They don't travel much or pull all-night strategy sessions. Mostly, the race is a test of a candidate's concentration and commitment, as he's put through a gauntlet of tedious, seemingly inconsequential public appearances.

The evening of July 29 offered just such an occasion. This was a candidate forum at a meeting of the Koinonia Worship Men's Group. The venue was a Pembroke Park temple that accommodates more than 100, but this event barely attracted 30. This included four candidates, their campaign entourages, two moderators, the pastor, and a lone member of the media. "There's not a single uncommitted voter in this room," Udolf growled through a fixed smile before the forum's start.

This was about the 20th candidate forum since June, and there would be roughly 20 more before the primary. A half-hour delay did nothing to attract stragglers. Having long since exhausted the interest of most voters, the forums have become a means for his supporters to ask softball questions of their favored candidate — and a shooting gallery for the candidates' enemies.

Case in point, the man who handed a moderator a question card that said, "Please have the Rule of One explained and how it affects placement into units." If that question sounds suspiciously technical coming from a church member, it's because it surely came from a rival candidate's staff seeking an opportunity to demonstrate Udolf's naiveté about law enforcement terms. But Udolf had done his homework, answering correctly that it referred to the policy for awarding promotions to an officer who scored highest on the civil service test.

No polls have been released that would give anyone a sense of who is winning the race, and though political insiders contacted for this article mentioned Scott Israel and Rick Lemack as co-leaders, that may be attributable to those candidates' powerful campaign managers — Judy Stern and Barbara Miller, respectively — who are both adept at creating buzz among Broward big shots.

"A lot of people are speculating based on who has what signs and what television ads, but this is a really difficult one to call," Udolf says. "I think I'm doing well, like we're in the place we want to be."

It may be a backhanded gesture of respect that Udolf and another candidate, ex-FBI agent Wiley Thompson, have been made the targets of anonymous fliers: The one that prompted a news conference from Udolf shows his face on a hayseed's body — presumably a reminder that he lives in the rural part of the county — alongside a list of his career lowlights, including a 25-year-old case from Udolf's stint as a DA in Georgia involving a man who was arrested in a drug sweep, then deprived of his civil rights. The man ultimately received a $50,000 settlement from the county. It was the same case Blumenthal had unearthed a decade before.

Neither Udolf nor Thompson have accused a specific rival of circulating those fliers, but since those low blows were struck, the two candidates have intensified their attacks on Israel, the police chief of North Bay Village. Israel, a former Fort Lauderdale cop, has enlisted the help of a few of the county's behind-the-scenes power brokers, notably lobbyist Judy Stern and Ron Cacciatore, an official with the county appraiser.

Policywise, few differences separate the candidates. They each promise to clean up any vestiges of corruption left from the Jenne regime. They each vow to reorganize so that anticipated budget cuts don't lead to a severe drop in services. They each want more-humane treatment of juvenile offenders and the mentally ill. And they each want to train deputies for a wider range of community functions. One gets the sense that if Jenne were in this forum, as opposed to his prison cell, he'd be making the same guarantees.

The tiebreaker, it seems, will be a combination of the candidate's qualifications and his ability to convince voters he's not susceptible to the temptations that unraveled Jenne.

Udolf has hammered Israel over his party affiliation, which was Republican as recently as last year. After Jenne's resignation, Israel appealed to fellow Republican Crist for an interview to fill the sheriff's job. Shortly after Crist refused, Israel switched his affiliation to Democratic. In doing so, he qualified for the primary.

In public appearances, Israel has explained that he always subscribed to Democratic principles but that he registered as a Republican when he was 18 because it helped him get a job in his native New York. Udolf calls that explanation "cock and bull," then offers a litany of reasons for voters to question Israel's integrity: the ten allegations of misconduct as a cop, some of which have disappeared from internal affairs archives; Israel's failure to land the chief's job in a host of Florida cities; and a campaign donor list that includes donations from Broward Sheriff's Office vendors — which, though legal, still raises concerns about influence peddling, the charge that brought down Jenne.

Udolf's own campaign disclosure forms show he's raised money from among the fraternity of former colleagues at the U.S. Attorney's Office, many of whom have graduated to private practice.

For his part, Israel has vowed not to play favorites and says he will "rebuild fences" damaged by Jenne's administration.

In an interview with New Times, Israel points out that none of the internal affairs allegations were sustained and, what's more, that the incidents represented a tiny fraction of the 1,500 arrests he made.

Israel has his own questions about Udolf's background. "As a defense attorney and prosecutor, perhaps his career has prepared him to run for judge or state attorney, but he's not prepared to run for Broward County sheriff," Israel says. "This is not a job for an attorney. This is a job for someone who has worked in law enforcement." At the Koinonia forum, Israel was even more explicit: "This job has my name written all over it."

Sitting in the next chair, Udolf rolled his eyes.

Israel, Udolf says, has exaggerated the importance of law enforcement experience. "If you want someone who's going to rappel from a roof and crash through your living-room window," Udolf says with a chuckle, "then maybe I'm not the candidate for you." He suggests the sheriff's job puts a premium on good judgment, where he claims a distinct advantage over his rivals.

At least one prominent campaign observer, Florida Sen. Steve Geller, believes this to be Udolf's fatal flaw. It may be true that recent history suggests prominent legal figures win the sheriff's race, but Geller believes that a candidate who has that in common with Jenne will be hard-pressed to win the public's trust. "After what happened with [Jenne], I think right now the public wants a sworn officer," Geller observes. "And I think Bruce thought it was business as usual and that a former prosecutor or judge could win the election."

Geller, who has represented Hollywood in the legislature for 20 years, has given his endorsement to Rick Lemack, former assistant chief of the Hollywood Police Department and the current assistant city manager. Lemack has been the most energetic campaigner, touting his pedigree of law enforcement experience and City Hall management. Of course, that experience took place in Hollywood, where the Police Department has been buffeted by corruption cases and where the city has blundered away millions of tax dollars. Lemack's name has not been linked to these failings, but any ties to that troubled city could spook voters.

Lemack denies it will be a factor. "A few people went the wrong way and have been disciplined," he says, "but it shouldn't overshadow the good that's being done in the city."


At the Miami Beach funeral of Steve Chaykin on August 4, Udolf was to be the last speaker, coming after Chaykin's brother, his sister, University of Miami President Donna Shalala, and several attorney friends. In his remarks, Udolf told of how in the years since they left the U.S. Attorney's Office, both he and Chaykin talked about how they'd love to return as the top man, finally in a position to make good on their ideals for busting bad guys. He closed by saying, "Someday, in my best moment, I hope to be a little more like him."

But to David DeMaio, an attorney who worked in that office with Udolf and Chaykin, their two characters had long since become identical. "He knew Bruce better than anybody," DeMaio says of Chaykin. "The fact that they were the best of friends, that speaks volumes — because of how carefully Steve picked his friends. All of the things you heard them say about Steve you could say about Bruce."

Chaykin would have been a contender for U.S. attorney had he lived to see his favorite candidate, Sen. Barack Obama, win the presidency this November. If Udolf fails to win the Broward sheriff's race, there's little doubt that he'll be angling to be the region's top federal prosecutor. And even if he does become sheriff, a U.S. attorney post might still entice him. "It's not an either/or situation," Udolf says coyly.

Whether he wins or loses his bid for sheriff, it seems the instinct that prompted his bid has been awakened. Udolf calls public service "the most rewarding work in my professional career," and it's clear that he's attracted to a specific public service: one that calls for heroism. "If the last elected sheriff wasn't sitting in jail and if there weren't scandals about falsification of statistics or deputies arrested for protecting what they thought was a narcotics organization, I wouldn't feel a burning need to do this," Udolf says. "I would make my return to public service in some other capacity — but this seemed to be the role where I could be most useful."


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