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Mr. Greenberg and Mr. Gaetz met through the tight-knit group of prominent Trump backers in Florida in 2017, according to a person familiar with the matter. Mr. Greenberg had no political experience before he was elected. Mr. Gaetz represents a district some 400 miles away.

Yet Mr. Greenberg and Mr. Gaetz saw each other regularly in recent years. They gathered at Mr. Dorworth’s home in January 2019 to celebrate that Gov. Ron DeSantis, a Republican close to Mr. Gaetz, had overturned a ban on smokable medical marijuana. The three men visited Washington together that June, and Mr. Greenberg posted photographs on social media from the White House lawn, including one of his daughter with Mr. Gaetz and Mr. Trump.

A few years ago — the exact date is unclear — Mr. Greenberg brought Mr. Gaetz into the tax collector’s branch office in Lake Mary over a weekend. The following Monday, an employee found the alarm deactivated and driver’s licenses strewn over a desk. She reviewed surveillance video and saw Mr. Greenberg with another man by that desk. When she asked Mr. Greenberg about it, according to text messages reviewed by The Times, he wrote back, “Yes I was showing congressman Gaetz what our operation looked like. Did I leave something on?”

What the men were doing is unclear.

In a separate episode on a Sunday in September 2018, Mr. Greenberg texted an employee about getting Mr. Gaetz an “emergency replacement” I.D. by Tuesday, claiming that the congressman had lost his. Mr. Gaetz told Politico that he had briefly lost his wallet but found it before needing the I.D. replacement.

Days after Mr. Greenberg was first indicted last year, a woman crashed her car into a tree a few hundred yards from his home early one morning, according to a crash report. The woman, according to two people familiar with their relationship, had previously had sex with Mr. Greenberg and received money from him on mobile payment apps; she had been leaving his house, the people said.

When a neighbor called 911, the woman was crying out incoherently in the background, according to a recording of the call. The neighbor said the woman was calling a friend. Moments later, an unidentified man could be heard on the caller’s end of the line.

“She got a bump on her head,” the man said. “There’s a little cut on her head. She’s just very shaken.”