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…

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.