Trump’s Well-Worn Legal Playbook Starts to Look Frayed

Mr. Korman, following the road map laid out in reporting by Wayne Barrett, The Village Voice muckraking journalist, investigated whether Mr. Trump had agreed to sign onto a landlord suit against an oil company being filed by a lawyer whose help he needed to acquire a large for-lease parcel of undeveloped land in Manhattan. Mr. Trump met with federal investigators, with no lawyer present, according to Mr. Barrett.

It was a roughly six-month investigation with a weak witness, according to people familiar with the work, with a statute of limitations approaching, making charges less likely to be brought. Still, the lesson that Mr. Trump appeared to take from it was that he had the ability to get himself out of difficult situations by persuading his antagonists.

When Eric T. Schneiderman, the New York attorney general at the time, began an investigation in 2011 into Trump University, looking into whether Mr. Trump’s for-profit classes claiming to instruct people on how to succeed in business were a scam, Mr. Trump first tried flattery and relationship building.

He hired Avi Schick, who had been the director of Mr. Schneiderman’s inauguration. But no deal with Mr. Schneiderman was negotiated, and eventually Mr. Trump accused Mr. Schick of being part of a ploy by Mr. Schneiderman to pressure Mr. Trump into donating money to his campaign in exchange for dropping the investigation. Mr. Trump bitterly complained that one of his company’s lawyers complied with Mr. Schneiderman’s for documents, Michael D. Cohen, Mr. Trump’s former fixer, recalled in a 2021 interview.

Mr. Trump fought the case until he abruptly settled it just after he was elected in 2016.

Since becoming president, Mr. Trump has been in search of his next Roy Cohn. When he was in the White House and a special counsel was appointed to investigate whether his campaign conspired with Russians in the 2016 election and whether he had obstructed justice, one of Mr. Trump’s first impulses was to meet with the people investigating him. He told his lawyers he wanted to sit with the special counsel, Robert S. Mueller III, at the outset.

Those lawyers declined to follow the president’s impulses. But some of his recent lawyers have given in to his desires, most often to attack aggressively.

“I think he thinks that everything can be bought or fought,” Mr. Rosenberg said, “and that is just not true.”