Dive Brief:

• Trump Organization CFO Allen Weisselberg said he steers clear of the “legal side” of the business’ dealings, according to 2015 deposition documents obtained by the New York Daily News. The deposition was related to lawsuits regarding Trump University, a for-profit education company the organization ran between 2004 and 2010. 

• Weisselberg, who has led the organization’s finances since the 1970s, claimed he had no interest in or knowledge of the legality of Trump’s spending, reportedly saying “that’s not my thing.” He has not publicly commented since the Manhattan District Attorney’s office began investigating him last month. 

• Weisselberg claimed to have been "eavesdropping" on legal-related conversations regarding Trump University, but ultimately backed away. "Throughout all of our entities, people do know it's important to involve me when it comes to financial matters,” he reportedly said.

Dive Insight:

The unearthed comments from the notoriously tight-lipped and loyal Weisselberg may mark a pivotal moment in the Manhattan DA’s ongoing probe.

Vance’s investigation began in 2019 with looking into hush money payments made to two women who said they had affairs with Trump. Former personal lawyer Michael Cohen arranged the payments and later pleaded guilty to campaign finance charges. 

Cohen testified to the House Intelligence Committee that while he personally paid Daniels on Trump’s behalf, Weisselberg “made the decision” to repay him over 12 months “so that it would look like a retainer,” the Daily News said. 

In his 2017 book, former Trump campaign manager Corey Lewandowski said Weisselberg "knows of every dime that leaves the building," according to Politico.

Prosecutors are searching for signs of financial fraud. Among other things, they're trying to learn whether the Trump family business "manipulated property values in order to receive loans and reduce property taxes," The Week reported. 

Weisselberg began working for Fred Trump in 1973, he testified, later shifting to work for former President Trump. 

“I was doing a lot of Donald’s work on weekends or at night,” Weisselberg said, according to the Daily News. “And that’s what eventually led me to leave Fred in 1986 and move into Manhattan to work for Donald.”

He began as controller and later became the company’s CFO. He called himself a “stickler” for details and claimed he spoke with Trump almost daily. During Trump's time in office, Weisselberg remained the organization’s CFO, and was the only non-family member to oversee his trust, Insider reported.

Prosecutors subpoenaed Weisselberg’s bank records last month. Weisselberg’s ex-daughter-in-law Jennifer was also served a subpoena for banking and tax records linked to Weisselberg’s son Barry, manager of several Trump Organization properties, including Central Park’s Wollman Rink.  

Ms. Weisselberg said prosecutors asked her about several gifts Trump and his company gave the family over the years, she told the New York Times, including an apartment on Central Park South, cars for several family members and private school tuition.

The Weisselbergs have not been accused of any criminal wrongdoing. But, to gain Allen’s cooperation, the Manhattan DA could leverage Barry and Jennifer’s failure to declare their gifts as compensation, the Daily News said.

Scrutinizing the gifts “appears to be part of an effort to paint a picture of Weisselberg’s financial life, as is common when prosecutors seek cooperation from a potential witness,” the New York Times said. “It is unclear whether prosecutors suspect any wrongdoing related to the gifts.”

Weisselberg's cooperation could provide the investigation "a significant boost" and could greatly jeopardize Trump, who has "long depended on Weisselberg's unflinching loyalty," the Times said in March.