Shark Tank's Kevin O'Leary Reveals Key Problem With Trump Fine

Businessman Kevin O'Leary, an investor on Shark Tank, told Fox News' Steve Doocy on Friday morning that Judge Arthur Engoron's judgment in the New York civil fraud trial against former President Donald Trump "probably infringed on the Eighth Amendment."

In February, Engoron ordered Trump to pay $355 million, plus interest, and banned him from doing business in New York for three years after finding him liable for financial fraud in a lawsuit brought by New York Attorney General Letitia James. Trump's two adult sons Donald Jr. and Eric, and two company executives, Allen Weisselberg and Jeff McConney, were also named in the lawsuit and suffered penalties.

Trump, who is the presumptive Republican nominee in the 2024 presidential election, has maintained that he has done nothing wrong and claimed that the case was politically motivated. He is appealing Engoron's ruling.

On Fox and Friends, Doocy asked O'Leary, who has been critical of Engoron's judgment, how he explains the case to people.

O'Leary/Trump
Businessman Kevin O'Leary (left) testifies before the House Committee on Small Business on January 18 in Washington, D.C. Former President Donald Trump speaks to press on March 19 in Palm Beach, Florida. O'Leary said on... Kent Nishimura/Joe Raedle/Getty Images

"This is no longer anything to do with Donald Trump whatsoever," O'Leary said. "This is very concerning to what you think of as the American brand. The reason that we're the number one economy on Earth is we provide stability in financial markets, through transparency, appellate systems in court, guarantee of law, property rights.

"And here is a situation...where an individual has had against an infraction an unduly high penalty, many people feel that on a bipartisan basis, probably infringed on the Eighth Amendment—has not been tested yet. That is where the problem lies."

The Eighth Amendment—part of the Bill of Rights in the U.S. Constitution—protects Americans from getting excessive bail, excessive fines, or cruel and unusual punishments.

O'Leary suggested that Engoron's damages trial was a mockery, comparing it to child's play.

"Most of us that are investors in financial services want the process to continue and get an appellate court involved here for a second set of eyes," he told Doocy. "The way I view this, and the way it's viewed internationally, is this was like dress-up court with kids running some kind of a Halloween party with no adult supervision. We need the adults now."

Newsweek reached out to Trump's campaign and lawyer via email for comment.

Dave Aronberg, the state attorney for Palm Beach County, Florida, who previously served as a Democratic state senator, told Newsweek via direct message on X, formerly Twitter, on Friday: "Calling a $464 million civil fraud judgment against a billionaire 'cruel and unusual punishment' is quite the reach. That argument will go nowhere on appeal."

Meanwhile, Vivek Ramaswamy, a bio-tech entrepreneur who ran against Trump in the Republican primary before dropping out and endorsing the former president, posted on X on Thursday: "The 8th Amendment was designed to protect against excessive fines or bail imposed to achieve unjust ends. Letitia James' crusade against Trump fits that to a tee. She should be disbarred."

Following Engoron's ruling in February, James posted on X: "Today, justice has been served."

"This is a major win for everyone who believes that we must all play by the same rules. No matter how big, how rich, or how powerful you are, no one is above the law. Not even Donald Trump," she said.

In order to stop the collection of his assets to pay Engoron's judgment, Trump must post a $454 million bond by Monday. However, the former president's legal team said in a court filing last Monday that it is a "practical impossibility" to come up with the money.

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Rachel Dobkin is a Newsweek reporter based in New York. Her focus is reporting on politics. Rachel joined Newsweek in ... Read more

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