Trump Organization and Top Executive Are Indicted in Tax Investigation

In the office, different sides of Mr. Weisselberg’s personality emerged. With Mr. Trump and his children, or anyone on his level or higher, he appeared mild-mannered, even solicitous. When he received good news about some financial matter, he would hurry down the hall to inform Mr. Trump, said Angel Lopez, who worked in the Trump Organization’s accounting department between 2007 and 2014.

“He always wanted to impress Donald Trump,” Mr. Lopez said.

With those who worked for him, Mr. Weisselberg could be collegial in one moment and volatile in the next. He would often accompany a few of the men in the accounting department to buy lunch at the same deli on West 56th Street. But if he perceived that someone made a mistake, he would yell so loudly he could be heard from behind his closed door, Mr. Lopez said.

Mr. Weisselberg acknowledged he could be a “micromanaging” boss.

“People do know it’s important to involve me when it comes to financial matters,” he said in the 2015 deposition. “Because later on, if things don’t prove out to be where they should be, they’ll have to deal with me on answering the question as to why.”

Mr. Weisselberg did not flinch when it came to denying raises or cutting bonuses to achieve Mr. Trump’s ends.

Rana Williams, who managed Mr. Trump’s sales and leasing division, accused his company in a 2013 lawsuit of illegally withholding $735,000 from her after the company reduced agents’ commissions to 25 percent from 35 percent as the financial crisis unfolded in late 2007.

After her plea to keep the commissions higher was rejected, she sent a letter explaining why she would continue to bill Mr. Trump at the 35 percent rate. Mr. Weisselberg scrawled a note to an assistant at the bottom: “Change Rana’s payment to 25 percent,” he wrote. “Ignore her letter.”

Mr. Weisselberg said in a deposition for that lawsuit that the company had every right to cut the commissions and that Ms. Williams had been free to leave. She testified that she held Mr. Trump responsible. “Allen was delivering a message,” she said.