Jimmy Kimmel Mocks Donald Trump's 'Very Dumb Crime Family'

Jimmy Kimmel has mocked Donald Trump, saying he's part of a "very dumb crime family," amid the former president's $250 million civil fraud case in New York City.

The 2024 presidential hopeful has in recent weeks been locked in an ongoing trial, in which he and his Trump Organization stand accused of having given misleading valuations for property they own to secure more favorable bank loans and tax arrangements. The case was brought by New York Attorney General Letitia James.

In September, Judge Arthur Engoron ruled that Trump, his sons and the Trump Organization had committed fraud. Republican election front-runner Trump has repeatedly denied any wrongdoing, branding the case against him a "witch hunt."

Engoron is currently deliberating on six other accusations, including falsifying business records and insurance fraud. As the case is civil, there is no prospect of Trump, or anyone else involved, being sentenced to jail.

Trump's adult sons—Eric Trump and Donald Trump Jr.—are also named in the lawsuit. The former president's daughter Ivanka Trump was initially named as a defendant because of her involvement within The Trump Organization, which she left in 2017. She was later removed from the list of defendants under the statute of limitations. Despite this, she was called up to testify in the trial last week.

During Monday's installment of Jimmy Kimmel Live!, comedian Kimmel played footage of Trump Jr. arriving at court, where bystanders were seen shouting "crime family" at him.

"That is basically what these people are, a crime family," Kimmel said after the footage was played. "A very dumb crime family. The Gambozos, if you will."

Kimmel went on to call Trump Jr. "so embarrassing," as he recounted that he called his father an "artist with real estate" while on the stand.

"Yeah, he's an artist. He's Vincent van Gogh-ing to jail with real estate," Kimmel quipped.

Later in his monologue, Kimmel played a clip of Trump attorney Alina Habba referring to Trump Jr. and Eric Trump as "boys" and "kids" as she stated that they should not be involved in the trial.

"That's right, they're just boys. They're kids," Kimmel said in response. "Eric has a book report due this weekend. They're both still wearing pull-ups."

Newsweek has contacted representatives of Donald Trump via email for comment.

It was recently speculated that Ivanka Trump's private communications could stand to negatively impact her father's case. At issue are potentially damaging emails, which Ivanka Trump was questioned about in court last week, because she was using a company email server.

Under normal court rules, any communication from one spouse to another is legally regarded as privileged and cannot be used in court.

Bucking this rule is the fact that Ivanka Trump wrote to her husband, Jared Kushner, on a Trump Organization email account. A judge ruled on Wednesday that her emails were admissible in the New York fraud trial of her father and brothers.

Over an objection from Trump's attorneys claiming spousal privilege, Ivanka Trump was questioned by Louis Solomon, a lawyer for the New York attorney general's office, about an email exchange she had with Kushner concerning potential funding from Capital One for the purchase of the Old Post Office in Washington, D.C., which was renovated and opened as the Trump International Hotel in 2016.

Kushner said he could discuss the deal with investment bank Natixis because he thought they would give the Trump Organization better terms. James' office firmly places Ivanka Trump at the center of that purchase and claims she used inflated asset evaluation to secure a loan.

Explaining the ruling that deems the Trump-Kushner emails admissible, attorney Colleen Kerwick told Newsweek that, under New York law, once someone writes to their spouse through a company computer server, a judge has to apply a four-step test to assess if their communication is too personal to be admitted into court.

That four-step test comes from a case involving billionaire businessman and financier Isaac "Ike" Perlmutter, the former chairman and CEO of Marvel Entertainment, who had allegedly written to his wife on company emails.

"As such, those communications were allowed into evidence and Ivanka was questioned about them. The issue of emails on a company server waiving privilege was previously before an Appellate Court in Peerenboom v Marvel Entertainment," Kerwick said.

The Marvel Entertainment case involved a four-step test, which was adopted to determine whether spousal emails on a company server were privileged or not. The case involved an unsuccessful defamation action against Perlmutter, which was taken by his neighbor Harold Peerenboom in Palm Beach, Florida.

Back in 2011, the men had a dispute over the management of a tennis court at the condo complex where they owned homes. During the dispute, Perlmutter and his wife, Laura Perlmutter, sent old news article clippings about Peerenboom to other residents in their complex.

Between 2012 and 2015, thousands of anonymous letters were mailed out to friends, relatives, Palm Beach neighbors, and professional associates of Peerenboom. In the communications, Toronto businessman Peerenboom was falsely accused of being a child molester, murderer and antisemite.

Peerenboom, founder of the executive search firm Mandrake Management, subsequently sued the Perlmutters, accusing them of being behind the hate-mail campaign. While the Perlmutters admitted to sending out the news clippings in 2011, they denied having anything to do with the letters sent between 2012 and 2015.

In that case, Peerenboom wanted to introduce emails between Perlmutter and his wife that were allegedly routed through a Marvel Entertainment server.

"The cornerstone of the Marvel Entertainment test is whether the emails are confidential or not. If they are not confidential then privilege would be waived," Kerwick told Newsweek. "I would hazard a guess that if Judge Engoron had not conducted an examination into the nuances of confidentiality, Team Trump may spin it into one of many building blocks for a mistrial."

While the lawsuit against the Perlmutters was eventually dismissed in 2021—with Canadian authorities tracing the letters in question back to a former employee of Peerenboom's company—it could now stand to affect the outcome of Donald Trump's trial, thanks to his daughter's emails.