Trump’s Legal Penalties Present a ‘Major Problem’: Former Prosecutor

Tristan Snell, a legal analyst and former New York assistant attorney general who helped lead the civil suit against Trump University, warned of a “major problem” underpinning former President Donald Trump’s recent civil fraud penalties.

Alongside the four criminal cases that Trump is currently facing, he has also in recent months faced a mounting number of civil trial verdicts that have carried increasingly hefty financial penalties. In two defamation cases brought against him by former Elle columnist E. Jean Carroll, Trump was found liable for sexually abusing her during a department store changing room encounter in New York City in the 1990s, and in turn for defaming her in 2019 and 2022 when he said that she was lying about the incident. As a penalty for each case, he was ordered to pay $5 million for the first verdict, and $83.3 million for the second.

Additionally, New York City Judge Arthur Engoron ordered Trump to pay roughly $355 million in penalties after he and his associates were found liable for a fraudulent scheme in which the value of his net worth and assets were inflated in order to obtain more favorable business deals. After interest, that payment will come to around $454 million.

Trump has frequently insisted on his innocence in all of these cases, even as doing so has possibly risked further legal action from Carroll. In order to launch appeals against these rulings, he has been required to pay bonds equal to or more than the penalties, which reports indicate that he has struggled to manage. On Friday, he was able to post the $91.6 million required to begin appealing the defamation ruling.

During a Sunday appearance on MSNBC, Snell warned that the possibility of outside parties helping with Trump’s appeal bonds could present a “major problem,” as they might then attempt to leverage that aid later if he is reelected president in November. Given his successful past efforts in prosecuting Trump for his Trump University program, Snell has often spoken out about the former president’s current legal battles and offered his insights into how they might play out.

“Everything in this case matters and everything should be explored by the court-appointed monitor, and everything should be explored by investigative journalists,” Snell said. “It was very clear that we were done to the wire on this [bond payment] and whether or not Donald Trump was going to be able to come up with that money. He kept trying to get extensions on it…he’s clearly having trouble coming up with cash.”

Snell continued: “He has the possibility of becoming President of the United States again. The possibility of interests, whether domestic or foreign, trying to buy the next President of the United States, possibly, by ingratiating themselves with him by coming up with this money to pay off his debts…this is a major problem, and this is something that everybody needs to be looking at very, very carefully.”

Newsweek reached out to Trump’s office via email for comment on Monday morning. Any responses received will be added to this story in a later update.

The $91.6 million bond that Trump posted in Carroll’s defamation case consisted of the $83.3 million judgment, along with statutory interest added by the State of New York. The bond was secured by the Federal Insurance Company, a part of insurance company Chubb Corporation.

In a Sunday interview on MSNBC’s Inside with Jen Psaki, Andrew Weissmann, the former general counsel for the FBI who also served as lead prosecutor in special counsel Robert Mueller’s investigation of Trump’s 2016 campaign, discussed the former president’s civil judgements.

“This is an example of running not just as an outsider, but as an outlaw…The concern in these civil cases with these civil judgements is who is the candidate beholden to. Is he somebody who is going to be making policy and being differential to people who have put up money?” Weissmann asked.

He later added: “There is a simple way of looking at this, is that he has $450 million reasons to be differential if somebody else is putting up the money or co-signing…That issue of who is actually behind this is something that people who are voting should know.”

Chubb chairman and CEO Evan Greenberg has history with the former president, having been appointed in 2018 to his Advisory Committee for Trade Policy and Negotiations during Trump’s presidency. The Washington Post recently reported it is “not clear from court records what collateral Trump presented to obtain the bond from Chubb.”

In a previous statement sent to Newsweek, Chubb said: “As a matter of policy, we do not comment on client-specific information. Our surety division provides appeal bonds in the normal course of business. These bonds are an ordinary and important part of the American justice system, protecting the rights of both defendants and plaintiffs. For defendants, appeal bonds ensure the opportunity to exercise the right to appeal an adverse judgment, which might otherwise be lost in the absence of a bond.

“For plaintiffs, appeal bonds ensure that they will receive the damages when an award is confirmed on appeal, eliminating the need to chase a defendant for payment. This guaranty provides peace of mind as a plaintiff awaits finality in the appeals process. The surety receives full collateral from the defendant in exchange for issuing the bond.”