"Not an open-and-shut case": Former U.S. attorney lays out remaining landmines for Trump prosecution

"A juror will likely say to themself, 'They had us here for all this time over misdemeanors? Really?'"

By Chauncey DeVega

Senior Writer

Published May 15, 2024 5:45AM (EDT)

Former US President Donald Trump attends his trial for allegedly covering up hush money payments linked to extramarital affairs, at Manhattan Criminal Court in New York City, on May 14, 2024. (JUSTIN LANE/POOL/AFP via Getty Images)
Former US President Donald Trump attends his trial for allegedly covering up hush money payments linked to extramarital affairs, at Manhattan Criminal Court in New York City, on May 14, 2024. (JUSTIN LANE/POOL/AFP via Getty Images)

The general consensus of most legal experts and other serious observers is that the first weeks of Donald Trump’s hush money trial in New York (what is really a trial about election interference and fraud) have gone very badly for the former president.

Key witnesses for the prosecution such as former National Enquirer publisher David Pecker, adult film actress Stormy Daniels, her attorney Keith Davidson, and then President Trump’s aide and confidante Hope Hicks have offered a damning portrait of Trump’s personal behavior, desire to hide his alleged affair(s) before the 2016 election, and pattern of using money to hide unflattering and potentially harmful information from the public.

The main witness for the prosecution, Donald Trump’s former attorney Michael Cohen, testified this week and "put it all together" for the jury, according to legal experts. The outcome of the hush-money trial – and if the charges rise to the level of a felony – appears to be greatly dependent on Cohen. His testimony and the hush-money trial have taken on even more extreme importance for the future of the United States and its democracy given that Trump’s three other criminal trials appear to be delayed past Election Day. In the end, the hush-money trial may be the only chance to hold Trump accountable for his decades-long crime spree. Public opinion polls show that a “guilty” verdict in the hush-money trial may sway enough voters to abandon the aspiring Dictator Donald Trump and vote for President Biden, in what is now a virtual tie.

But there are some legal experts who hold the unpopular view, one contrary to what so many Americans and members of the mainstream news media and political class (and especially the “Resistance”) desperately desire and want to believe, that a guilty verdict in Trump’s hush-money case is not a fait accompli or in any way a certainty. Kevin O’Brien is one such voice.

"In a criminal case, if you're a prosecutor, you'd like to have the conduct required for conviction to line up with the ethical significance of the case. But here, they are totally different."

A former assistant U.S. attorney who specializes in white-collar criminal defense, commercial and securities litigation on behalf of plaintiffs and defendants, regulatory enforcement cases, and arbitrations, O'Brien is currently a Partner at Ford O'Brien Landy LLP. His legal analysis and expert commentary have been featured at NBC News, BBC News, Salon, Bloomberg News, Vox, Scripps News, Reuters, Westlaw Today, and Law360.

In a conversation with Salon, O’Brien explains that the charges against Trump are highly technical and suggests that the prosecution will likely have a difficult time proving Trump’s direct role in falsifying his business records, a requisite for the charges to rise to the level of a felony.

He also shares his concerns that there are jurors who find themselves annoyed that Trump, a former president, is being charged with hiding an affair and that does not rise to the level of a serious crime. O'Brien is concerned that the defense’s emphasis on the sexual and other lurid details of Trump’s encounter with Daniels may also have the effect of turning jurors in favor of the corrupt ex-president.

This interview has been lightly edited for clarity and length:

How are you making sense of Trump's hush-money trial and the larger maelstrom around his multiple criminal trials? This is all truly historic and unprecedented, and not in a good way. It is also very exhausting. 

I had mixed feelings about the hush-money case before it started. The charges are almost unworthy of a former president. Moreover, the statute seemed technical. In a criminal case, if you're a prosecutor, you'd like to have the conduct required for conviction to line up with the ethical significance of the case. But here, they are totally different. The charged conduct is creating false business records, which carries little ethical weight. The prosecution is going to have to prove that Donald Trump intended to create or abet, enable, and assist the creation of false business records. These records certainly appear to be false. But how did he actually falsify the records? That is the key matter. Perhaps Mr. Cohen will provide that link. It has not been compellingly established yet in the hush-money case by the prosecution. 

You are most certainly an outlier, especially among the types of voices who are being featured in the mainstream news media, on certain cable news networks, as well as here at Salon, who are generally presenting Trump's first criminal trial as almost a fait accompli. I am on the record as being very concerned about the hush-money trial (and the other ones as well) and how too many public voices are being prematurely happy and celebratory about Trump being found guilty and that somehow leading to his demise. This is not an open-and-shut case despite how many people would like to believe it is.

It is not an open-and-shut case at all.

"The jury is going to be instructed that these are just misdemeanors. A juror will likely say to themself, 'They had us here for all this time over misdemeanors? Really?' That's a good argument in favor of the defense."

Given the nature of juries and criminal cases, all it takes is one or two jurors who aren't overwhelmed by the proof. A juror who says to himself that yes, what Trump did was bad, and he acted in a disgusting way as he often does, but where is the crime here? How does this violate the public's trust? I believe that we are being swayed by the tense and dramatic atmosphere of this first criminal trial. The witnesses are colorful and interesting — and they have baggage of their own.

Let me be clear, I believe that the prosecution has done a great job. They are very well-prepared and very professional. They have also thought of all the angles that should have been considered so far. They have also thought deeply about their strategy. But in the end, the prosecution may not have the evidence to prove their case conclusively. Moreover, I am concerned that the prosecution may have gone overboard on the sexual details of Trump's encounter with Stormy Daniels. There may be one or two jurors who were put off by that and feel like the prosecution is just trying to embarrass Donald Trump. Yes, Trump denied having a relationship with her and you want to prove that he in fact did have one. But all the extra details may not have been necessary.  

Pushing back a bit. There is all the evidence that has been presented in court so far, for example a recording of Trump talking about the hush-money payments. There are also the witnesses including Trump's aides and confidantes, the former publisher of The National Enquirer David Pecker, Karen McDougal's attorney who handled her alleged hush-money payment, and Stormy Daniels herself who have painted a damning portrait of Donald Trump's behavior. I am sure many people reading our conversation will be very surprised that you are not convinced that Donald Trump is already defeated in this first criminal trial. 

I don't think Donald Trump is dead to rights. The case against him is not overwhelming. And even if the prosecution can prove everything that they have alleged, the weight of the charges does not fit what the facts and evidence show. There might be people who suspect that they wouldn't have gone after anyone other than Donald Trump about these matters and therefore this is a political prosecution. I can easily see one or more jurors having such a thought in a way that can create reasonable doubt. The charge is, again, somewhat technical. It's not intuitive. The jurors must connect the strong ethical condemnation of hiding material facts from the electorate on the eve of an election, which is the ethical thrust of the entire case, from the actual charged conduct, which has nothing to do with it. 

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The charges against Donald Trump are for falsifying business records. If I were the prosecutor, I would want to have proof of a conversation where Trump admits that we've got to call these hush-money payments legal fees or something else in order to buy off Stormy Daniels. Moreover, because Trump is a former president, it seems to me that the prosecution is probably going to be held to a higher standard of proof of guilt by the jury. 

If found guilty will Donald Trump be sentenced to prison? 

These criminal offenses come with a range of possible sentences. Falsifying business record records are misdemeanors. And in that case, you can't serve more than a year, that's the maximum for any misdemeanor. And most people convicted of misdemeanors, at least the first time around, get no time served, they get probation. But if they can link that to a predicate crime, like election fraud, which is what the state is trying to do, or tax evasion, then they can bump the charges up to a felony. But even so, I think the range is going to be on the low end given the nature of the offense. Will a judge sentence Donald Trump to prison for these offenses? I can see an argument that given Trump's public stature as a former president that some prison time may be warranted. No man is above the law. But even then, I believe the sentence would be for only a few months, and he may just get probation. Trump does not care about being fined.

The argument being made by the prosecution is that the hush-money payments were part of a larger attempt in service to hiding information from the public to help Donald Trump win the presidential election. How hard is that going to be to prove? 

It's not a crime in New York to mislead voters or to make false statements to the electorate on the eve of an election. But it is a crime, albeit a misdemeanor, to make false entries in business records. The jury is going to be instructed that these are just misdemeanors. A juror will likely say to themself, "they had us here for all this time over misdemeanors? Really?" That's a good argument in favor of the defense. Yes, that reaction is not based on the evidence. But human commonsense reactions have an impact on how jurors make their decisions. And such a reaction may also be common among prospective voters as well. The prosecutors are going to have to compellingly connect this all to an attempt to defraud the public as part of something much bigger. 

What strategy and approach would you use to defend Donald Trump? Would you present him as someone sympathetic and a victim who is being persecuted or as a horrible person who has done many bad things but one who is not guilty of what he is being charged with in the hush-money trial? The latter approach seems more compelling to me as opposed to the "family man" line that his defense used in their opening statement. How do you find a balance?

If you were operating on a blank slate as a defense lawyer, the latter approach is far preferable. It's easier to pull off. It levels with the jury and you are letting them into your confidence, that is seductive. We all know that this guy isn't a great person, right? But where's the crime? That could be an effective approach in a case like this. Here is the problem: Donald Trump is not going to let his lawyers make that pitch to the jurors. I assume Trump's attorneys said all that stuff about him being a "family man" because he demanded that they do it. For the same reason, I assume that the cross-examination of Stormy Daniels, which became kind of pointless, was done at Trump's request. He wanted her to be embarrassed and shamed on the stand. He wanted her to be punished because he was angry at what she has said about him and their intimate encounter. I'm sure Donald Trump instructed his lawyers that they had to go after Stormy Daniels with everything they had, even though that's often not the wisest approach. I don't think it was the wisest approach here. They've got a very demanding client with Donald Trump who is insistent that certain things be done even if they aren't the wisest things to do in the case. 

When you are dealing with a difficult personality like Donald Trump, what is your approach as an attorney?

Donald Trump can be his own worst enemy. But past a certain point, you have to make peace with your client. As an attorney, you can take a hard line on certain things. If you're a forceful person with a track record of success you may be able to get away with it for a while, but inevitably, you're going to have to bow to the client's wishes. If you don't you will get fired. There has already been talk about how Trump is not happy with his lead attorney Todd Blanche. The hush-money trial is maybe only half over. No lawyer wants to get fired from a trial, especially so after all the work they've put in.

Why is Donald Trump not in jail for repeatedly and flagrantly violating the court's gag orders about threatening witnesses and engaging in other menacing and intimidating behavior against people involved in the trials?

Donald Trump is in the middle of an election campaign. This judge, and likely no other judge, would put Trump in jail for violating a gag order. What Trump is doing is certainly improper, but there's not much a trial judge can do. In a criminal case the defendant needs to be there. Someone who is not only a former president, but is a leading candidate, a judge is going to bend over backwards to avoid putting him in jail. I just don't see it happening. Frankly, the things that Trump says are outrageous. But I believe that part of why he is getting away with this behavior is that there has not been some type of high-profile incident where his followers have been incited to serious violence. There may have been things that have happened that the Secret Service and other law enforcement are keeping close to the vest, but we don't know that.  So far at least, the hush-money trial has proceeded without serious incident. Trump's bad behavior with the gag order and his threats and the like is one issue that I believe the press has made too much of.

What is going on with the three other criminal cases against Donald Trump? The so-called legal walls that are supposed to be closing in on Donald Trump appear to have stopped, again.

The Georgia case was likely never going to trial until well after the election. It is a huge case. They indicted too many people. Too many small potatoes were swept up in the indictment. They didn't need to do that. Fani Willis decided she wanted to tell a sweeping story, which does have some merits as an approach. But in the end, the practical problems with such an approach are great in terms of time. Matters are not getting easier in the Georgia case given the attacks on her personal conduct. She is also in a hostile political environment. The Republican legislature doesn't like her. I'm sure a number of the judges don't think much of her either. So, she's got to be careful, and she wasn't. 

By comparison, special counsel Jack Smith has done a wonderful job with the cases in Florida and for Jan. 6 and the attempt to subvert the 2020 election. Unfortunately, the federal courts have proved to be an obstacle. The Supreme Court taking this appeal on a fairly simple question that they've made into an enormous philosophical debate about presidential immunity is going to mean the Jan. 6 election interference case will not get tried before the election. 

The case in Florida is even worse. Judge Aileen Cannon apparently doesn't want the case tried. There's apparently nothing that the government can do about her. I assume they thought about moving to have Cannon disqualified at the very beginning, but they opted against it because they felt that they could not win. Accusing a judge of bias or the appearance of bias is a very serious matter. We are now paying the price for that decision.  The classified documents case is a very simple one with the fewest obstacles to conviction. There is almost no defense to anything that Donald Trump did, but nevertheless, we're not going to see a trial for quite a while — and certainly not before the 2024 presidential election.  

By Chauncey DeVega

Chauncey DeVega is a senior politics writer for Salon. His essays can also be found at He also hosts a weekly podcast, The Chauncey DeVega Show. Chauncey can be followed on Twitter and Facebook.

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