Mr. Caputo attributed his tax problems to his poor skills as a businessman, saying that he opened a public relations business in South Florida without much background in finance.

By 2008, he said, he had fallen far enough behind in his tax payments that the federal government filed a lien against him for $52,788. He said he had worked out a payment plan with the I.R.S. and now owes $9,302. He declined to provide documentation of the payments.

“Most people I know have had problems paying their taxes,” he said. “I am just like everybody else.”

In the early 1990s, Mr. Thompson, Mr. Paladino’s driver, was charged with driving under the influence, damaging a vehicle in a hit-and-run and driving with a suspended license, according to Arizona court records. Mr. Thompson recalled that he had been drinking at a family barbecue, argued with his wife and drove off to avoid making a scene. But he said he hit another car and was arrested.

Records show that he served jail time in connection with the charges.

At one point, according to the records, an arrest warrant was issued after Mr. Thompson failed to show up for a court hearing. Mr. Thompson said he was unaware of the warrant. But he said that, after he completed his jail time, he moved out of Arizona at the suggestion of his probation officer. “I have never looked back, and I really don’t care to look back,” he said, in a second, more relaxed interview.

Mr. Thompson, a Tea Party organizer who is credited with encouraging Mr. Paladino to run for governor, said that he had not drunk alcohol in 20 years, since around the time he was arrested in Arizona. “I saw the course I was on,” he said, adding that he did not like it. “So I gave it up. It was the lowest point in my life.”

Two of Mr. Paladino’s campaign advisers have been accused of misdeeds involving large sums of money. His chairwoman, Nancy A. Naples, decided not to seek re-election as Erie County comptroller in 2005 after The Buffalo News reported that she had directed 80 percent of the county’s bond business to one of her campaign donors.