The campaigns of Andrew Gillum and Ron DeSantis are ideologically opposed in almost every way: on healthcare, the NRA, education and, of course, President Donald Trump. But despite their once-outsider status, both nominees have a key similarity: a senior leader who is a well-connected Tallahassee power broker who has cultivated relationships in Florida’s capital for decades.
Those two veteran lobbyists — Sean Pittman and Nick Iarossi — run so closely in the same circles that they have worked together on issues, consider each other friends and even work out together in their personal time. Reared in the same political cradle at Florida State University, both were also among the first investors in the downtown Tallahassee restaurant that has become the center of the FBI probe that is now being used to hammer Gillum’s campaign.
But the two men are now on opposite sides of a governor’s race that has given Floridians one of their most ideologically stark contrasts for the job in recent memory. Pittman, a campaign senior adviser, has been a Gillum confidant since before his city commission days, while Iarossi holds a prominent fundraising role in the DeSantis operation.
How did DeSantis and Gillum, once considered unlikely to advance past the primary, come to rely on consummate capital insiders in the race?
The answer — and where Pittman and Iarossi’s paths first crossed — starts at Florida State in 1994 when Pittman was just graduating from law school and Iarossi was enrolling as a freshman from upstate New York.
Though seven years apart, they quickly became acquainted through student government that school year. Pittman had served as student body president when he was an undergraduate and Iarossi would soon have aspirations for the same role.
“I was helping some friends who were running for student body president at Florida State when I was in law school or just out of law school,” Pittman, 49, said. “Nick was a freshman, and he was involved in that race. … We just gravitated toward each other.”
Pittman, an involved alum, continued to orbit in student government circles throughout Iarossi’s years in college, and Iarossi helped out during Pittman’s unsuccessful run for county commission in 1996.
Iarossi, 42, declined to comment on the record but acknowledged his friendship with Pittman and that he volunteered on Pittman’s 1996 campaign.
When Iarossi began to contemplate his own run for student body president, Pittman said he also offered one-on-one advice on how to campaign successfully, drawn from his own race. The advice might have helped: Iarossi won outright in a five-way primary.
The two men’s paths continued to mirror each other after Iarossi graduated with a bachelor’s in 1998 — like Pittman, he also stayed at Florida State for law school, graduating in 2001.
“If you look at it — we’re a few years apart — we both were involved in student government, we both became student body president, we both went to FSU law school, we both clerked for the same firm,” Pittman said.
Pittman opened his eponymous law and government consulting firm in 2001, while Iarossi clerked at the Department of Insurance and joined another law firm where he was encouraged to dip into lobbying. Two years later, Iarossi helped open Capital City Consulting, where he has remained since.
Both lobbyists have also built political clout — Pittman, who ran Gillum’s 2014 campaign for mayor and has remained a close adviser, focuses on representing local governments in his firm and is a substantial subcontractor of powerful Tallahassee lobbyist Ron Book. Iarossi, whose clients for Capital City have included a variety of gambling interests, has also become a veteran GOP fundraiser.
But the two have worked together on occasional issues, from the Everglades to puppy mill regulations. They also have another kind of work: a shared morning workout at Primal Fit Tallahassee, a gym on the east side of town.
Something else also became a common tie in the last few years: an investment in the Edison, the posh taxpayer-subsidized restaurant downtown that is now a subject of the FBI’s investigation. Both Pittman and Iarossi were among a handful of investors in the project — though some of the project’s other backers remain unknown. (Iarossi said he sold his stake in June.)
But the Gillum vs. DeSantis matchup has pitted the two against each other in a way prior races have not. Whoever wins becomes the governor of the third most populous state in the country, with a thumb on the scale via veto power that in Gillum’s case could be brought to bear against a presumably Republican-majority Legislature.
Both candidates during the primary campaigned as underdogs who at one point trailed in polls and lacked establishment backing. But Pittman’s and Iarossi’s roles on the campaign signal that despite those stances, both candidates are leaning on resources rooted deeply in the state capital’s culture to succeed.
“The fact that we’re both engaged at the levels we are in the race, in these two races, is probably in line with our stories,” Pittman said. “I don’t think it’s unusual.”