Why getting a conviction against Donald Trump may not be so easy

A grand jury has voted to indict former U.S. president Donald Trump on charges relating to hush money payments made in 2016 to a porn actress. But making that case, some legal experts say, could be challenging for Manhattan District Attorney Alvin Bragg.

Credibility of lawyer Michael Cohen, and Trump's intent, may hamper Manhattan district attorney

Former President Donald Trump pumps his fist after speaking at the Conservative Political Action Conference, March 4, 2023, Oxon Hill, Md. The Manhattan district attorney's office appears to be getting close to a decision on whether to charge Donald Trump over hush-money payments to Stormy Daniels during his 2016 presidential campaign.
Former U.S. president Donald Trump pumps his fist after speaking at the Conservative Political Action Conference on March 4 in Oxon Hill, Md. A grand jury has voted to indict Trump over hush-money payments to Stormy Daniels during his 2016 presidential campaign. (Alex Brandon/The Associated Press)

Donald Trump's intent, and a star witness who is also a convicted felon are just some of the challenges that the Manhattan district attorney will face in trying to secure a conviction against the former U.S. president on charges relating to hush money payments made in 2016 to a porn actress.

"This case is going to have serious, serious problems," said Mark Bederow, a criminal defence attorney and former New York City prosecutor.

Bederow, who was interviewed by CBC News before a grand jury voted to indict Trump on Thursday, said that the decision by Manhattan District Attorney Alvin Bragg to pursue formal charges was "stunning." 

But others say Trump shouldn't be too confident; the case against him could be stronger than some have suggested. U.S. attorney Norm Eisen, who was co-counsel for the House Judiciary Committee for Trump's first impeachment trial, praised Bragg's efforts to take this case to a grand jury.

"The allegations here are of a very serious criminal wrongdoing. And I think the proof is strong," Eisen said.

The case centres around a $130,000 US payment made by Trump's former personal attorney, Michael Cohen, to Daniels through a shell company set up by Cohen. Cohen was then reimbursed by Trump, whose company logged the reimbursements as legal expenses.

Trump has denied an affair with the actress, Stormy Daniels, but the payment made to her, to keep her quiet, is not in dispute.

Manhattan District Attorney Alvin Bragg exits a building, Wednesday, March 22, 2023, in New York.
Manhattan District Attorney Alvin Bragg exits a building, Wednesday, March 22, 2023, in New York. Bragg could face many challenges trying to convict Trump of a felony. (Eduardo Munoz Alvarez/The Associated Press)

That payment was recorded by the Trump Organization as a legal expense. And it's that recording that has the former president facing a possible criminal trial. He could be charged with falsifying business records, a misdemeanor, and also face a more serious charge of falsifying business records in the first degree — a felony.

The potential legal problems for Trump are two-fold. Did he falsify this business transaction in the Trump Organization by recording the payment to Daniels as a legal expense? And, more seriously, if he falsified the record, was the intent to commit another crime, specifically, evading campaign finance laws?

Cohen has pleaded guilty to violating U.S. campaign finance law in connection with the payments. Federal prosecutors say the payments amounted to illegal, unreported assistance to Trump's campaign. However, they declined to file charges against Trump himself.

Now, nearly five years after Cohen's guilty plea, Trump faces his own charges related to the payment. Here are the challenges the district attorney may have in making the case, and the difficulties Trump's legal team could face defending him. 

The potential misdemeanor

Under New York state law, it's a crime to falsify business records. 

"It's as simple as it sounds, if you falsify business records for any purpose, and you do so intentionally, then you can be convicted of a misdemeanor," Bederow said. 

But David Shapiro, a financial crimes specialist and former FBI special agent, said indicting Trump for a misdemeanor would be "unusual." Normally, he said, prosecutors seek indictments for serious crimes. 

"A misdemeanor, normally you wouldn't even hear about it. It wouldn't rise to the level of a district attorney's awareness. It would stay in a local court," he said. "What gives this case potential heft is the scheme to defraud."

The potential felony

The payment to Daniels occurred during Trump's campaign for president. The legal issue here is whether the recording of the payment in Trump's books was falsified in order to evade federal campaign finance laws.

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The allegation is that paying for Daniels' silence, and avoiding the embarrassment of an alleged affair, would help Trump's presidential campaign, and therefore should be considered a campaign expense. Such an expense would be required to be disclosed to the Federal Election Commission. But the amount paid to Daniels would have exceeded the legal limit of $2,700 US. 

"[If] it's a cover up to essentially evade federal campaign finance law, [Trump] can now be prosecuted for a felony," said Leo Glickman, a New York-based lawyer who specializes in campaign finance, election and voting rights law.

"The idea here is that the only reason why he paid off Stormy Daniels was to advance his candidacy for president."

Donald Trump's former lawyer, Michael Cohen, speaks to reporters on March 15 after a second day of testimony before a grand jury investigating hush money payments he made on the former president's behalf in New York. Cohen's credibility could be an issue for the prosecution. (Mary Altaffer/The Associated Press)

But Bederow believes it could be difficult to prove Trump's intent was to defraud. A jury, he said, could conclude it was reasonable that Trump's only purpose of concealing the payment was to avoid embarrassment with his wife or children for any connection he had to Daniels, and to prevent harm to his business reputation.

"That has nothing to do with necessarily either intending to defraud, or more importantly, trying to conceal a crime," Bederow said.

Demonstrating that the whole arrangement was to cover up Cohen's payment to ensure such knowledge wouldn't hurt his presidential campaign, will be a "hell of a task, I think, for the prosecution here," Bederow said.

But Eisen scoffed at that potential defence. He said Trump would have to show there was no element of campaign intentionality, "no element whatsoever," regarding the payment to Daniels.

"Who does he think is fooling? Even for a serial fabricator like Donald Trump, this is beyond the pale," said Eisen, the attorney who worked on Trump's impeachment. "I do not accept that bad defence will succeed. No jury will buy that."

The credibility of Cohen

One of Bragg's biggest liabilities, said Bederow, could be his key witness: Michael Cohen.

"Michael Cohen is the worst witness imaginable that a prosecutor could have for several different reasons," Bederow said.

Most significantly, Bederow said, Cohen is a convicted felon, having pleaded guilty to campaign finance charges and of lying to the U.S. Congress. 

"It's not often that the star witness literally has a conviction for making false statements under oath," Bederow said. "It's not a good starting point for any prosecutor."

Bederow said it's obvious that Cohen has a personal disdain for Trump, which could raise questions about his motivation to testify.

But prosecutors often have to rely on people who themselves were culpable in a crime, Eisen said.

"[Cohen] accepted responsibility for what he did wrong. And his story on the hush money payment has absolutely not varied right since he began cooperating. I know because he was one of the first witnesses that I talked to when we were doing the impeachment." 

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Eisen agreed that the cross-examination of Cohen would be "colourful and tough." 

"I believe he's telling the truth. He's rough around the edges and colourful himself but I think he's going to withstand cross-examination."

Statute of limitations

Trump could benefit from the time it's taken Bragg to bring a case against him to court.

The statute of limitations for this kind of litigation is usually five years. And since the payment was made in 2016, more than six years have passed.

However, if a defendant has been out of state, then the statute of limitation can be "toiled" or suspended during that period. And Trump, having been in D.C. for four years as president, was out of state.

"But it's hard to believe the legislature would have intended ... that serving as president of the United States counts as being out of state," Shapiro said.


Mark Gollom

Senior Reporter

Mark Gollom is a Toronto-based reporter with CBC News. He covers Canadian and U.S. politics and current affairs.

With files from The Associated Press