In the weeds

New York prosecutors have subpoenaed a Manhattan private school as they seek the cooperation of the Trump Organization’s chief financial officer in their investigation of former President Donald Trump and his company, according to people familiar with the matter.

The subpoena seeks information from Columbia Grammar & Preparatory School, where grandchildren of Trump Organization CFO Allen Weisselberg are students, the people said. From 2012 to 2019, more than $500,000 of the children’s tuition was paid for with checks signed by either Mr. Weisselberg or Mr. Trump, the two children’s mother, Jennifer Weisselberg, told The Wall Street Journal. She is the former wife of Mr. Weisselberg’s son Barry.

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Columbia Prep is a private school of roughly 1,300 prekindergarten through high-school students on Manhattan’s Upper West Side. Tuition this academic year ran more than $50,000.

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Ms. Weisselberg said she told Manhattan prosecutors that she and Barry understood the tuition payments to be part of her ex-husband’s compensation package at the Trump Organization, where he worked.

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Ms. Weisselberg told the Journal she and her ex-husband never paid their children’s tuition. She said she delivered some checks to the school that were signed by Mr. Trump. She said others, beginning around 2015, were signed by Allen Weisselberg.

  WSJ

About the time Trump decided to run for president.

Let me guess why he paid Weisselberg this way...Trump can claim a bigger tax break on the kids' tuition. Not to mention, he doesn't have to pay any employee-related taxes on it.

And Weisselberg gets a break, too.

Former prosecutors not involved in the probe said the Manhattan district attorney’s office could be examining whether the Weisselbergs evaded taxes with the tuition-payment arrangement.

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Mr. Weisselberg has worked for the Trump Organization for decades and is regarded as Mr. Trump’s confidante and his company’s financial gatekeeper. Mr. Weisselberg hasn’t been accused of wrongdoing.

They may be squeezing Weisselberg to cooperate in their investigations of Trump himself.

In 2017, Mr. Weisselberg became a co-trustee charged with managing the president’s business assets.

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People who know Mr. Weisselberg say he is faithful to the Trump Organization, and they questioned whether he would ever breach that loyalty.

I can't imagine Trump hired anyone with morals, so I'd say it depends on the extent of the penalty he might pay. 

 ...but hey, do what you want...you will anyway.

UPDATE: