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Prosecutors with Manhattan District Attorney Cyrus Vance Jr.'s office have subpoenaed a Manhattan private school to see whether the Trump Organization paid the tuition of longtime financial chief Allen Weisselberg's grandchildren, The Wall Street Journal reports, citing people familiar with the matter. If former President Donald Trump's business paid the tuition, it would be considered taxable income, tax experts told the Journal, and if that income wasn't reported to tax authorities, it could constitute tax fraud.

Vance's office is trying to gain the cooperation of Weisselberg as it tries to untangle the Trump Organization's byzantine financial records, according to multiple reports. Jennifer Weisselberg, who was married to Weisselberg's son Barry until their divorce, told the Journal that Trump or Allen Weisselberg signed checks for more than $500,000 to Columbia Grammar & Preparatory School to cover tuition for her and Barry's two children from 2012 to 2019. The couple understood the tuition payments to be part of Barry's Trump Organization compensation package, she added.

Divorce documents filed by Barry Weisselberg said his parents paid the children's tuition to the Upper West Side private school because he couldn't afford to, and the Weisselberg family characterized the payments as a gift, the Journal reports. If the grandparents paid the tuition directly to the school as a gift, that would not be taxed, but if the Trump Organization paid the tuition, the Weisselbergs could be in legal jeopardy.

"Without an insider it can be difficult to put all the pieces in a white-collar case together," Daniel Horwitz, a white-collar defense lawyer at McLaughlin & Stern, told the Journal. "The way that cooperation is typically obtained is by demonstrating to the potential cooperator that they have no better option."