Donald J. Trump, who has repeatedly denounced pay-to-play politics during his insurgent campaign, is now defending himself against claims that he donated $25,000 to a group supporting the Florida attorney general, Pam Bondi, to sway her office’s review of fraud allegations at Trump University.
Mr. Trump’s payment of a $2,500 penalty to the Internal Revenue Service over that 2013 campaign gift amounted to only the latest slap of his wrist in a decades-long record of shattering political donation limits and circumventing the rules governing contributions and lobbying.
In the 1980s, Mr. Trump was compelled to testify under oath before New York State officials after he directed tens of thousands of dollars to the president of the New York City Council through a myriad subsidiary companies to evade contribution limits. In the 1990s, the Federal Election Commission fined Mr. Trump for exceeding the annual limit on campaign contributions by $47,050, the largest violation in a single year. And in 2000, the New York State lobbying commission imposed a $250,000 fine for Mr. Trump’s failing to disclose the full extent of his lobbying of state legislators.
For the most part, Mr. Trump has seemed unrepentant. Testifying in 1988 about a $50,000 bank loan he had first guaranteed, and then repaid, on behalf of Andrew J. Stein’s successful campaign for New York City Council president, Mr. Trump made no bones about the move.
“I was under the impression that I was getting my money back,” he told the New York State Commission on Government Integrity.
In the Florida case, Mr. Trump is accused of using a large and timely political donation in 2013 to ward off a potentially thorny investigation by Ms. Bondi’s office: Days before the donation was made, The Orlando Sentinel reported that the New York State attorney general’s office had sued Trump University and noted that Ms. Bondi’s office was weighing whether to join in that litigation.
A political aide to Ms. Bondi told The Associated Press earlier this year that the attorney general had solicited the donation in a conversation with Mr. Trump weeks before the Sentinel’s article. But Mr. Trump made the donation from his charitable foundation, in violation of tax regulations, and paid the penalty, as first reported by The Washington Post reported last week.
Mr. Trump and Ms. Bondi, who is supporting his campaign, have denied any connection between his donation and her office’s decision not to proceed with an investigation. Asked about the subject on Monday, he called Ms. Bondi “beyond reproach” and said he “never spoke to her about that at all.”
A spokesman for the Florida attorney general’s office, Gerald Whitney Ray, said the office’s inquiry never came across Ms. Bondi’s desk: Lower-level staff members made the decision not to proceed with an investigation of their own. Mr. Ray also said the office never gave any thought to joining in the New York attorney general’s case.
But Democrats and liberal watchdogs seized the opportunity to accuse Mr. Trump of practicing exactly the sort of corrupt politics that he rails against on the campaign trail.
Campaigning in Tampa, Fla., on Tuesday, Hillary Clinton demanded details of the conversation in which Ms. Bondi solicited Mr. Trump’s donation. “The American people deserve to know what was said, because clearly the attorney general did not proceed with the investigation,” she told reporters.
And Jordan Libowitz, a spokesman for the liberal-leaning Citizens for Responsibility and Ethics in Washington, said Mr. Trump’s donation to Ms. Bondi gave new meaning to his more recent boasts about the efficacy of his political giving. “It sure looks like that is what is going on here,” said Mr. Libowitz, whose group filed a complaint about the donation with the I.R.S.
Though Mr. Trump denies it in the case of Ms. Bondi, he has been brazen in asserting that he has used political donations to buy influence and routinely asks voters to trust that, because he possesses that insider’s knowledge, he can reform a system that he calls “rigged.”
During a Republican debate last summer, Mr. Trump responded about his ability to curry favor with public officials when he was confronted with one of his own statements: “When you give, they do whatever the hell you want them to do.”
“You’d better believe it,” Mr. Trump responded. He added: “When they call, I give. And you know what? When I need something from them two years later, three years later, I call them, they are there for me.”
Indeed, Mr. Trump’s history of political giving stretches back decades — and has repeatedly drawn regulatory scrutiny.
When a New York State commission investigated contributions to state and local officials in the 1980s, it subpoenaed Mr. Trump, who had contributed $150,000 to candidates in 1985. Under oath, he said he had circumvented the state’s $50,000 individual and $5,000 corporate contribution limits by disbursing his contributions to Mr. Stein, the city councilman, through 18 subsidiary companies.
“My attorneys basically said that this was a proper way of doing it,” Mr. Trump testified.
In an interview, Mr. Stein said he did not recall what Mr. Trump had sought in return for his contributions, or for a $50,000 campaign loan that Mr. Trump first guaranteed and then repaid. He denied ever agreeing to do Mr. Trump any favors.
Years later, Mr. Trump came under fire from the Federal Election Commission for violating a $25,000 annual limit on contributions in the late 1980s. Mr. Trump resisted paying a fine, insisting that he had been unaware of the federal limit and that, once informed of it, he sought refunds.
Only when the commission threatened to take him to court did Mr. Trump agree to a $15,000 civil penalty, records show.
It was with similar reluctance that in 2000, Mr. Trump apologized for failing to disclose to New York State officials that he had spent $150,000 to finance ads opposing a proposed casino in the Catskills, which he saw as a threat to his Atlantic City properties. The ads were created and placed by a political consultant, Roger Stone, and appeared under the name of a front group, the Institute for Law and Society.
A settlement led to what, at the time, was the largest penalty imposed by the state lobbying commission: Trump Hotels and Casino Resorts paid $50,000, and Mr. Stone and the front group each paid $100,000, without admitting wrongdoing. In a statement, all three said they “apologize if anyone was misled.”
In recent years, Mr. Trump has made tens of thousands of dollars in contributions to at least four state attorneys general Ms. Bondi of Florida and Greg Abbott of Texas, both Republicans, and the Democrats Eric Schneiderman of New York and Kamala Harris of California whose offices have looked into complaints about Trump University.
Mr. Abbott, whose office considered a lawsuit against Trump University before the company left Texas in 2010, is now supporting Mr. Trump who donated $35,000 to Mr. Abbott’s successful 2014 campaign for governor.
Ms. Harris’s office said it, too, was investigating the company, and an aide said she donated the $6,000 from Mr. Trump to charity.
Mr. Schneiderman’s fraud lawsuit is still pending. But Mr. Trump, whose donation of $12,500 to Mr. Schneiderman preceded his election, filed a state ethics complaint alleging that Mr. Schneiderman continued to seek donations, calling the fraud case a “shakedown.”
The state ethics panel declined last year to pursue Mr. Trump’s complaint.
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