Community involvement and business connections give Bill Segal an advantage in the race for Orange County mayor. But the ‘insider’ label is fodder for his foes.
One day in 2003, Bill Segal decided he was tired of being asked to contribute money to unworthy candidates for local elective offices—people who sought jobs on the public payroll and hit up developers like him to help fund their campaigns.
“I was sitting at this desk seven years ago,” Segal, 60, recalls in an interview at the cluttered Winter Park office of his now-inactive development firm. “I got the typical invite [to a candidate fundraiser] that we all get. The ‘donor class.’ People like me who would give. And all the people on the host committee were the usual suspects—friends of mine. And I called one of them up and I said, ‘Who is this guy?’ He said, ‘Look, he’s a nice enough guy that needs a job. Vote for him. [Orange County Mayor Rich] Crotty likes him. Vote for him, or send him a check or something.’”
It was the kind of candid, behind-the-scenes phone conversation that happens countless times each election cycle in a place where
developers’ dollars are the mother’s milk of politics. Not quite a shakedown, but not exactly a high-school civics lesson, either. It was somewhere in between—just the way business gets done.
“So I ruminated on the thing and sat here. And I talked to my wife,” Segal continues. “And I said ‘You know, this is the problem. Good people won’t run for public office. And now is the time to do it.’”
So instead of writing that check, Segal decided to get into politics himself—even though winning would eventually mean winding down his development business and taking a substantial pay cut. He jumped into the race for District 5 Orange County commissioner, outraised all his opponents and was elected in 2004. Today, he is campaigning from that perch as one of four major candidates for a job with a much higher profile—Orange County mayor.
Segal’s main opponents are current and former colleagues on the board, Linda Stewart and Teresa Jacobs, respectively, and political newcomer Matthew Falconer. Another rival, recently suspended county Commissioner Mildred Fernandez, appeared all but officially out of the race at presstime. Fernandez was arrested April 27 on felony charges of bribery, grand theft and accepting illegal campaign contributions. Gov. Charlie Crist immediately suspended her
Segal is far and away the financial frontrunner, having raised nearly $600,000 from contributors through the end of March. His four opponents combined had raised only about two-thirds that amount from outside contributors by that date.
As the Aug. 24 primary approaches in the nonpartisan race, Segal’s fundraising prowess—aided by business, civic and political connections he’s made over the years—has cast him in a role he was born to play: Mr. Establishment.
A ‘Lifetime Person’
Segal’s father, the late Martin Segal, was a prominent local lawyer and financial whiz who moved among Orlando powerbrokers in the 1960s. Young Billy Segal grew up in College Park, an Edgewater High School kid with a front-row view of a world where his dad helped governors, mayors, bankers, judges, newspaper publishers and a klatch of prominent businessmen make important things happen.
Most famously, the elder Segal brokered the deal for the final holdout to sell the last, small parcel of land needed to assemble the mass of property for Walt Disney World. Most infamously, he was swept up with dozens of people in a 1971 indictment alleging that his law firm helped bankroll Central Florida crime kingpin Harlan Blackburn’s illegal gambling operation. The charges were never proven.
Today, Bill Segal says he wants to bring to the region’s most powerful elected office the perspective that comes with his lifelong Orlando roots and his experience as a successful businessman.
Besides working in appointed or elected government posts since 1993, Segal has served as a board member for civic groups ranging from the Coalition for the Homeless to the now defunct Florida Symphony Orchestra and the Orlando Museum of Art. His wife, Sara, is on the board of the Orange County League of Women Voters and a leader in numerous arts and social service
“Of all the people running, I’m the one that has the business ability, the business background, the grounding here in this community,” he says. “[I’m a] lifetime person. We’re an inclusionary area. You don’t have to be from the area. But it does give you some advantages of knowing how things got to be the way they are.”
Though he says he wouldn’t choose the title “Mr. Establishment” for himself, he embraces all that it suggests.
“Well, you pretty much know who’s doing what in the community,” he says. “You know where the expertise lies. You could convene the health care providers in town. Know them by their temperament. You know who’s a real doer and who is just a ‘face person.’ You know who you can count on to follow through for the community.”
Indeed, Segal is well-established in Orlando’s social and political circles. Go to just about any prominent charity gala or well-attended social function in town and you likely will run into Segal. His standing as a political insider was all but confirmed in early April when three local mayors—Orlando’s Buddy Dyer, Winter Park’s Ken Bradley and Belle Isle’s Bill Brooks—announced their support of Segal outside the county administration building. Dyer said he rarely, if ever, has endorsed a local candidate since becoming mayor.
Segal says his main goals as county mayor would be to run a tight financial ship, protect money for public safety, strengthen ties with the school district and use his knowledge of business and economics to attract big employers to Orange County. But Segal has offered few specifics on his vision for the county while some of his opponents have rolled out detailed platforms on their websites. Segal promises that more specifics will come as the campaign heats up.
Being the clear favorite of the “donor class” to which he once belonged definitely has its advantages in the mayor’s race, but it also has spurred other candidates to attack him as the “insider” who is most at home in smoke-filled rooms rubbing elbows with local fat cats.
For example, Segal was recently put on the defensive after the Orlando Sentinel reported that he had not removed himself from numerous commission votes over the years involving a developer to whom he had financial ties. Segal didn’t disclose his conflict of interest until the newspaper questioned him about it before a vote related to the developer in April.
Segal’s low-key affability has been painted as the trait of a politician more interested in getting along than taking charge.
“Well, Bill is a very nice guy, but his sense of initiative in his six years of incumbency has been very small,” says Doug Head, former chairman of the Orange County Democratic Party, who has endorsed Stewart over Segal even though both are Democrats.
Head, who today is on the board of the Orange County Watch government accountability group, also says it “just drove me nuts” in 2007 when Segal dismissed ethics reform as a concern only of the “chattering class.”
That remark is ripe for a negative ad as Segal’s opponents depict him as a politician who’s beholden to special interests. In today’s political climate, candidates who are outgunned financially can position themselves as “outsiders” as a way to tap into the free-floating public anger at government at every level.
Of his opponents, Segal says only Falconer can lay legitimate claim to the outsider’s mantle. Fernandez was elected to the county commission the same year as Segal, and Stewart and Jacobs both have served two years longer than he. But all three women have seized on Segal’s presence at a few men-only gatherings of something called the “No Name Club” as a way of hammering the “smoke-filled room” theme in a literal way.
A local land-development lobbyist hosted the bimonthly parties in 2009, which featured fine cigars, gourmet meals and top-shelf booze. Segal was at three of the gatherings, Crotty went to two and Commissioner Scott Boyd was at one. After the Orlando Sentinel raised questions about whether the opulent affairs violated a ban on gifts from lobbyists to elected officials, the three men reimbursed the host, attorney Fred Leonhardt, $50 for each event they attended.
But Segal rolls his eyes at the suggestion that there was anything nefarious about the gatherings. He compares them to hundreds of events he says he attends each year—ranging from Rotary Club meetings to routine galas and benefits for civic organizations.
Segal expresses annoyance that such routine schmoozing can become campaign fodder. He dismisses charges that such events are evidence of public corruption as almost cartoonish, resulting from disingenuousness or naiveté. Likewise, he rejects the notion that businessmen-turned-elected-officials like him have something to hide when they balk at ethics rules that would require them to disclose the names of all their current or former business associates.
Any successful businessperson, he says, will have a complex history of legitimate relationships and past financial connections with many companies, attorneys, individuals and consultants. Those names can often be difficult to remember over time, let alone track and disclose in a coherent way. Imposing such stringent disclosure requirements, he says, validates a simplistic, black-and-white view of the world where anything can be portrayed as a conflict of interest and the most capable people are effectively disqualified from seeking office. The main target of his ire is Jacobs, who as a commissioner fought but failed to win the battle for the strictest ethics rules—
and who as a candidate has called for a formal probe of Segal’s
“Jacobs kept talking the whole time [during the debate over new disclosure rules] about how she only has a car, two jet skis and a house,” recalls Segal. “The world looks very simple to people that look through that prism—people that have no assets or have never been involved in the business world. The world looks so
Jacobs’ response? “My prism is indeed, simply, honest and open government.”
Segal made good money as a developer of small residential and commercial properties. His latest financial disclosure form lists his net worth at about $2.9 million. But he hardly lives the high-flying life of the proverbial Florida developer. He and Sara live in a 1,700-square-foot Winter Park home. He drives a 2005 Toyota pickup and doesn’t wear jewelry or flashy clothes.
And it’s unfair to cast him as an unwavering supporter of insider causes. Segal has frequently stood up against development interests as both a county commissioner and during his eight years on the St. Johns River Water Management District board.
He says his father’s reputation was unfairly smeared in the Harlan Blackburn saga. And Segal acknowledges that the long-ago episode left him with a heightened sensitivity today to how ordinary business dealings can be twisted into something more ominous—if not necessarily a belief that more transparency in such matters would be helpful.
“Oh, it’s guilt by association. It’s always guilt by association,” he says.
But in the long run, such slings and arrows don’t matter, he says. For Mr. Establishment, the good parts of campaigning for mayor always outweigh the bad.
“I’m happy with being a well-known member of this community who has served 30 years before I got into politics, in a myriad of public service [capacities],” he says. “It’s not something
new to me.”