How Tallahassee insiders became friends and leaders on opposite sides of governor’s race

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?

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