Dive Brief:

• As part of its continued probe, the Manhattan District Attorney’s Office has subpoenaed school tuition payments for the Trump Organization CFO Allen Weisselberg’s grandchildren, the Wall Street Journal reported Thursday.

• The subpoena seeks information from Columbia Grammar & Preparatory School, where Weisselberg’s grandchildren are enrolled, sources told the Journal. According to Weisselberg’s estranged ex-daughter-in-law Jennifer, between 2012 and 2019, more than $500,000 of the children’s tuition was paid for with checks signed by either Weisselberg or former President Donald Trump.

• District Attorney Cyrus Vance Jr. has been seeking Weisselberg’s cooperation through the probe since at least March. Weisselberg, who has not been accused of any wrongdoing, has worked for the Trump family since the 1970s, is considered a loyal family confidant.

Dive Insight:

The DA is likely examining whether the Weisselbergs’ tuition payment set-up qualifies as tax evasion. Additionally, putting pressure on a suspect’s family can be a means of encouraging cooperation, which has been Vance’s main objective.

Jennifer Weisselberg told Vance’s office she and her ex-husband, Barry Weisselberg, understood the tuition payments to be part of Barry’s compensation package at the Trump Organization, where he worked, according to the Journal. She added that she and Barry “never” paid the tuition themselves, and gave the school checks signed by President Trump or by Allen Weisselberg.

The tuition in question is for Columbia Prep, a private school on Manhattan’s Upper West Side, where the cost to attend this academic year exceeded $50,000. President Trump’s son, Barron, attended the school prior to the family’s move to Washington, and Trump’s former personal lawyer, Michael Cohen, was the school’s board chairman, the Journal found.

The probe began with Vance looking into the Trump Organization's role in making hush money payments to two women who alleged they had had extramarital affairs with Trump.

Cohen testified before Congress that Weisselberg devised a strategy to hide that the Trump Organization was reimbursing Cohen for making a $130,000 payment to one of the women, adult actress Stormy Daniels. 

The probe has since grown and narrowed its focus on Weisselberg, including subpoenaing his bank records, in an attempt to find whether the Trump Organization falsely reported property values to secure loans and tax breaks, the New York Times said.

Scrutinizing Trump’s gifts to the Weisselbergs “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.

Weisselberg has said he doesn't involve himself in the legal issues of things he's asked to do, but legal specialists have said that ignorance is a hard strategy for any CFO to claim.