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Who is Allen Weisselberg, Donald Trump’s ultra loyal former CFO? The 76-year-old began working for Fred Trump 50 years ago and even appeared on The Apprentice – now he’s off to jail for a second time

Retired Trump Organisation CFO Allen Weisselberg has just been sentenced to 5 months in prison for perjury. Photo: Getty Images/TNS
It’s hard to keep up with all of Donald Trump’s criminal cases these days, let alone the key players in each one.

Trump is currently sitting as a defendant in a “hush money” trial in New York, making it the first time a former president has gone to trial on criminal charges. He is accused of covering up payments to adult film star Stormy Daniels, who claims she had an affair with him.

But just days before the trial began, former Trump Organisation CFO and The Apprentice star’s most trusted accountant, Allen Weisselberg, was sentenced to five months in prison after pleading guilty to perjury, admitting he lied under oath about Trump’s assets.

Despite the ageing retiree coming under extreme pressure to turn on his former boss, Weisselberg has remained ultra loyal to the Trump. Here’s what you need to know about him …

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He lied under oath

The Trump Organisation’s former CFO Allen Weisselberg at the Manhattan Criminal Court in New York on March 4. Photo: Reuters

This April, Weisselberg was sentenced to five months in prison after he admitted to perjury. Weisselberg had claimed in a 2020 deposition that he did not know about errors linked to the size and value of Trump’s Manhattan penthouse until after an article by Forbes showed that the Trump Organisation had inflated it by three times in its financial statements.

Weisselberg had also claimed he was not present during an interview with Trump and Forbes where the size of the penthouse was interrogated. Forbes later showed evidence of Weisselberg not only being at the interview, but also that it had sent several emails to him before the article was published.

Allen Weisselberg has remained loyal to Donald Trump despite the significant personal cost to himself. Photo: Reuters
The charges brought by New York Attorney General Letitia James allege the Trump Organisation falsely inflated the value of its assets for personal gain, “to induce banks to lend money to the Trump Organisation on more favourable terms than would otherwise have been available to the company”.

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The Stormy Daniels case

Former President Donald Trump is currently on trial in New York in a so-called hush money case. Photo: AP
According to Forbes, Weisselberg was also involved in the so-called hush money scheme, for which Trump is currently on trial in New York. Per the publication, Weisselberg helped Trump repay lawyer Michael Cohen for a payment made to Stormy Daniels before the 2016 election. The money was allegedly paid to Daniels (real name Stephanie Clifford) in a bid to cover up her allegations that she’d had an affair with Trump. The payments were falsely labelled as legal costs, per Forbes. Consequently, Trump faces 34 counts of falsifying business records.

Weisselberg’s long-standing history with the Trumps

Weisselberg’s history with the Trump family dates back over 50 years. He was first hired by Donald Trump’s father Fred in 1973. Per USA Today, Weisselberg soon became a trusted insider at the Trump Organisation and was asked to manage all of its assets. In the late 1980s, he established the accounting departments for the Trump Organisation, managing both the company and Trump family members’ tax returns. He also managed the finances of the Trump properties.

Weisselberg’s close bond with Trump

Allen Weisselberg, right, stands behind then President-elect Donald Trump during a news conference in the lobby of Trump Tower in New York in 2017. Photo: AP
In 1986 he began working directly with Donald Trump, according to USA Today. The two apparently share a close bond, with Trump trusting Weisselberg with control of his company along with his children when he became president back in November 2016, per the BBC.

In 2004, Weisselberg even appeared on an episode of Trump’s reality show The Apprentice. According to The New York Times, those who worked with Weisselberg described him as a “soldier”, unflinching in his support for Trump. “Over decades, Mr Weisselberg’s personal and family life became increasingly fused with the company and with Mr Trump, who is just 14 months older,” the newspaper wrote.

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Previous Trump jail term

Former Trump Organisation CFO Allen Weisselberg is a long-time executive for Donald Trump’s business empire. Photo: AP

This month’s sentencing is not the first time Weisselberg has gone to prison for his involvement with the Trump family either. In 2022, Weisselberg pleaded guilty to 15 counts of tax fraud, serving about 100 days in New York’s famous Rikers Island jail, per CNN.

According to Forbes, the charges related to Weisselberg being given “gifts” and other compensation that was not taxed by the Trump Organisation, including payment for a New York flat, luxury cars and school tuition for family members. He was released in April last year.

Donald Trump
  • As Donald Trump’s ‘hush money’ trial continues in New York – the first time a former president has been in court on criminal charges – a key player close to him was sent to prison in a separate case
  • Allen Weisselberg, who’s just 14 months younger than The Apprentice star, has been working for the Trumps for 5 decades, and has just been sentenced to 5 months for perjury