Mr. Weisselberg has served as executive vice president and chief financial officer at the Trump Organization, and was once described by a person close to the company as “the most senior person in the organization that’s not a Trump.” After Mr. Trump was elected, he handed control of his financial assets and business interests to his two adult sons and Mr. Weisselberg.
.. Mr. Weisselberg, a reserved accountant associates say is prized by Mr. Trump for his loyalty, has handled personal financial matters for Mr. Trump and has also been linked to payments made to two women who alleged they had sexual encounters with Mr. Trump.
.. During his effort to secure the retainer, Mr. Cohen showed Mr. Weisselberg records that he said related to expenditures he had made on behalf of Mr. Trump from his personal home-equity line of credit, this person said.
.. In the recording, which Mr. Cohen secretly made and which is under review by federal investigators, Mr. Cohen said he would set up a company to make the payment, adding, “I’ve spoken with Allen Weisselberg about how to set the whole thing up,” before Mr. Trump interrupts him.
.. Later in the conversation, Mr. Cohen reiterates that he “spoke with Allen” about the plan to finance the payment.
.. Mr. Cohen’s repeated references to Mr. Weisselberg in his conversation with Mr. Trump about buying the story were interpreted by others in the company as an effort to bolster Mr. Cohen’s credibility, according to a former associate of Mr. Weisselberg.
.. Mr. Weisselberg’s ties to the Trump family date back to days of working for the real-estate firm owned by Mr. Trump’s father, Fred, in the 1980s. He later came to the Trump Organization, where he reported directly to Donald Trump and worked out of an office in Trump Tower.
He was long an understated presence—one former colleague told the Journal in 2016 that Mr. Weisselberg “fits in with the wallpaper”—but with a temper that flared at times and an ability to crunch numbers rapidly
.. Mr. Weisselberg long performed tasks such as arranging for checks that Mr. Trump would sign, but also took on an increasingly large role at the company. If he thought there might be questions about whether or not to pay a supplier the full amount the Trump Organization owed, he would direct executives to check directly with Mr. Trump, one former executive said.
Over the years, Mr. Weisselberg has handled dealings with banks and other important matters, according to the former executives. He oversaw many of Mr. Trump’s personal transactions, the Journal has reported, citing a former Trump executive, including paying household expenses as well as the purchases of boats, planes or other personal properties.
For years, at least through the financial crisis, Mr. Weisselberg prepared Mr. Trump’s tax returns, according to one former Trump Organization employee.
Another former executive said Mr. Trump would sometimes point out to him how Mr. Weisselberg had been loyal to him for decades. In the course of business meetings, Mr. Trump also at times would reflexively ask his CFO to confirm his opinion. During one meeting, in 2015, Mr. Trump turned to Mr. Weisselberg and asked, according to a person who was there:
“Isn’t that right, Allen?”
“One-thousand percent right,” Mr. Weisselberg responded.