Andrew Gillum, a Florida Insider Running as a Progressive Outsider

“Does he have friends who are lobbyists? You bet,” said Allan Katz, a former city commissioner who served with Mr. Gillum and later became Mr. Obama’s ambassador to Portugal. “Did I have friends who were lobbyists? You bet.”

And as Mr. Gillum seeks the state’s highest post, at least one of those friends has brought baggage, dragging his name into an F.B.I. investigation and, unbeknown to him, placing him in the extended company of undercover agents. About two years ago, a lobbyist, Adam Corey, who had been close with Mr. Gillum since their student government days, introduced him to men who identified themselves as out-of-town developers eager to invest in property on Tallahassee’s south side — but were in fact working undercover to investigate the city’s community redevelopment agency for possible corruption.

Mr. Gillum has insisted that investigators told him he is not their target, and the inquiry has yet to produce any indictments. But subpoenaed documents revealed that Mr. Gillum took two personal trips in 2016 with Mr. Corey: one to Costa Rica with a top Gillum adviser, Mr. Pittman, and another to New York with Mr. Gillum’s younger brother and the agents. Mr. Gillum has said he paid his own way for most of the travel, with his brother treating him to a Broadway performance of “Hamilton” and a hotel stay. Both trips are under investigation by Florida’s state ethics commission. Mr. Gillum’s younger brother, Marcus, declined to comment, and a lawyer for Mr. Corey declined to provide further case details.

Mr. Gillum’s defenders have said any whiff of impropriety is inconsistent with the man, and the city, they know.

“There is no corruption in the city of Tallahassee,” Curtis Richardson, the city’s mayor pro tempore, said in an interview. (Later, he seemed to hedge slightly: “It’s not like it’s systemic corruption, and multiple individuals are involved, and it’s from the top down. It’s not that at all.”)

Mr. Katz, the former commissioner, said Mr. Gillum had been too ambitious, for too long, to behave recklessly. “He always was looking for a political future for himself and was therefore, I think, extremely careful,” Mr. Katz said. “But all of us who’ve been involved in politics sometimes wind up in the wrong room with the wrong guy.”

Mr. Gillum has chafed most at the labels applied to him as the investigation churns, which he believes fail to capture the totality of the affair. “You only put people in characters: ‘lobbyist and mayor,’” the mayor said of the lobbyist matter during a 45-minute interview at a local coffee shop. “I have a very easy time saying no to friends.”

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