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Former Trump Organization CFO receives five-month jail sentence

As if Team Trump weren’t already struggling with an avalanche of legal troubles, the Trump Organization's former CFO will now be behind bars.


In the summer of 2021, Donald Trump faced a major legal setback. A New York district attorney’s office brought charges against the former president’s business, the Trump Organization, as well as Allen Weisselberg, the Republican’s long-serving and trusted chief financial officer, alleging widespread tax fraud.

Initially, Weisselberg pleaded not guilty. Then, as regular readers might recall, he reversed course, changed his plea to guilty, and agreed to pay taxes, interest and penalties.

This was not, however, enough to prevent a jail sentence. NBC News reported:

Allen Weisselberg, former chief financial officer for the Trump Organization, was sentenced Tuesday for his role in the company’s sweeping 15-year tax fraud scheme. Weisselberg, 75, received five months behind bars, in accordance with his guilty plea, during an appearance before acting Justice Juan Merchan in New York criminal court.

An Associated Press report added that he will be eligible for release after little more than three months if he behaves behind bars.

This comes about a month after a jury in New York found the Trump Organization guilty on 17 counts, including scheme to defraud, conspiracy, criminal tax fraud, and falsifying business records.

Weisselberg’s name may not be familiar to national audiences, but when it comes to the former president’s business, few players are as important. The Wall Street Journal reported a while back that Weisselberg was described by a person close to the company as “the most senior person in the organization that’s not a Trump.”

NBC News’ Katy Tur spoke to a former Trump Organization employee who added that Weisselberg “knows where all financial bodies are buried within the Trump Organization.”

As the former CFO heads to New York City’s notorious Rikers Island jail complex, it’s worth pausing to appreciate the "culture of lawlessness" surrounding the former president — which, as regular readers know, continues to get worse:

  • Trump’s former campaign chairman, Paul Manafort, was charged, convicted, and sentenced to prison.
  • Trump’s former campaign vice chairman, Rick Gates, was charged, convicted, and sentenced to prison.
  • Trump’s former personal lawyer, Michael Cohen, was charged, convicted, and sentenced to prison.
  • Trump’s former adviser and former campaign aide, Roger Stone, was charged, convicted, and sentenced to prison.
  • Trump’s former White House national security advisor, Michael Flynn, was charged and convicted.
  • Trump’s former campaign adviser, George Papadopoulos, was charged, convicted, and sentenced to prison.
  • The Trump Organization's former CFO, Allen Weisselberg, was charged, convicted, and will spend the next few months behind bars.
  • Trump’s former chief strategist, Steve Bannon, was charged with wire fraud and money laundering.
  • Though he was later acquitted at trial, Trump’s former inaugural committee chair, Tom Barrack, was charged with illegally lobbying Trump on behalf of a foreign government. (Elliot Broidy was the vice chair of Trump’s inaugural committee, and he found himself at the center of multiple controversies, and also pled guilty to federal charges related to illegal lobbying.)

And, of course, the former president's business was itself found guilty of tax fraud.

To be sure, some of the aforementioned men were ultimately pardoned by Trump, who doled out pardons as party favors before exiting the White House, but this doesn’t change the "remarkable universe of criminality" surrounding the Republican.

What’s more, with multiple ongoing investigations, it's entirely possible this list will grow. It might even someday include the former president himself.

Circling back to our earlier coverage, the number of criminals is important, but so too is the degree to which this dynamic conflicts with the story Trump was eager to tell about himself. For years, the Republican presented himself as being aggressively “tough on crime,” which he frequently tried to incorporate into his political message.

In 2019, for example, while making the case for a border wall, the then-president declared, “The Democrats, which I’ve been saying all along, they don’t give a damn about crime. They don’t care about crime.... But I care about crime.”

Trump cared so much about crime that he apparently surrounded himself with criminals.