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Trump and Trump Org are in prosecutors’ crosshairs. But what does that really mean?


While former President Donald Trump is doing all he can to remain public and relevant after his election loss, there’s one thing he undoubtedly wishes people would ignore: the mass of criminal investigations that have been building momentum since the end of his presidency. Freed from the legal and practical concerns about indicting a sitting president, a number of prosecutors’ offices have been charging ahead with criminal investigations of Trump, his organization and his associates.

Freed from the legal and practical concerns about indicting a sitting president, a number of prosecutors’ offices have been charging ahead.

Last week, New York Attorney General Letitia James confirmed that her office is pursuing a criminal investigation of the Trump Organization. In the past few months, the Manhattan district attorney has finally obtained the Trump Organization’s financial documents from its accountants, a district attorney in Georgia is investigating criminal allegations that Trump tried to illegally influence the election results in the state, and federal prosecutors in Washington, D.C., may be looking into whether Trump should be charged with playing a role in the attack on the U.S. Capitol on Jan. 6. Recently, the U.S. attorney’s office in Manhattan also executed search warrants at the home and offices of Rudy Giuliani, Trump’s personal attorney, based on allegations that Giuliani engaged in illegal lobbying on behalf of a foreign government. These reports of subpoenas, search warrants and witness interviews have put what are typically confidential investigations squarely in the public view.

Given all this activity, many Americans may well be wondering why Trump hasn’t been criminally charged with … well, something.

A criminal case generally falls into one of four categories. There are small cases brought against small targets (most of the thousands of criminal cases filed every day), big cases brought against small targets (think the Oklahoma City bombing), small cases brought against big targets (Martha Stewart’s prosecution for lying about an insider trade that saved her about $50,000) and big cases brought against big targets (such as Rep. William Jefferson, D-La., who was convicted of bribery in 2009 and sentenced to 13 years).

A former president of the United States is unquestionably a big target and therefore falls into either category three or four. But there are risks to both approaches.

Let’s assume a prosecutor wants to pursue a category four case — that is, a big case against Trump. Such a case would be likely to involve complex financial transactions, such as those resulting in huge, questionable tax refunds to the Trump Organization, a focus of New York’s attorney general and Manhattan’s district attorney.

The problem is that complexities can open the door to potential defenses in a criminal trial. Putting aside the enormous task of collecting, analyzing and summarizing all of the documents (a job that the Manhattan DA’s office has wisely outsourced to an expensive consulting firm), the prosecution must also prove criminal intent, which can be challenging when the target heads a large organization. In fact, the typical defense offered by tax evaders — “my accountants prepared my returns and I just signed them” — hasn’t gone unnoticed by Trump, who has already pointed out that his tax returns were prepared by “among the biggest and most prestigious law and accounting firms in the U.S.” It could be a heavy lift to convict a former president of any kind of business fraud when he has surrounded himself with lawyers and accountants.

That is why the cooperation of those same lawyers and accountants can be essential to obtaining a criminal conviction. Michael Cohen, Trump’s convicted former attorney, is enthusiastically cooperating against his former boss, and there is immense pressure on Allen Weisselberg, the chief financial officer of the Trump Organization, to do the same. But both men come with considerable baggage — Cohen is a convicted felon, and Weisselberg is under investigation of allegations of tax misdeeds of his own — that might impair their credibility at trial.

So if a big category four case includes too many problems, should prosecutors consider charging a smaller case from category three — for example, a single misstatement on a bank loan application? Such a charge could perhaps come out of the New York state and Manhattan probes.

Maybe, but bringing a small case against a big target carries its own risks. Such cases leave the impression, perhaps unfairly, that either the defendant isn’t being prosecuted for the full scope of his or her illegal conduct or that the defendant is being singled out for prosecution simply because he or she is a high-profile person. Neither takeaway seems particularly satisfying.

In fact, it’s possible that all of the above concerns played roles in the apparent decision by New York federal prosecutors not to pursue charges against Trump over allegations that he made “hush money” payments to Stormy Daniels; the Federal Election Commission has similarly declined to take any action regarding those payments.

And finally, what about Jan. 6 attack on the Capitol or Trump’s phone call to Georgia Secretary of State Brad Raffensperger, which may have violated Georgia election laws?

Both would be big cases, but they would also be politically charged cases, and therein lies another problem for prosecutors. Prosecutors know a criminal charge isn’t a conviction. There is a world of difference between obtaining a criminal indictment, which requires only “probable cause,” and a criminal conviction, which requires a finding that the defendant is “guilty beyond a reasonable doubt.” The latter is, for good reason, the highest burden of proof that exists in our legal system.

Prosecutors know they should bring criminal charges only if they believe they can convict the defendant; to operate under any other standard would be unethical. That is true no matter who the defendant is, but in the case of a high-profile defendant, prosecutors aren’t likely to file charges unless they are as certain as humanly possible that they will be able to obtain a conviction. And because prosecutors must convince an unanimous jury of 12 ordinary citizens that a defendant is guilty beyond a reasonable doubt, bringing a politically charged or divisive case puts that certainty further out of reach.

Which brings us back to the question: With all these investigations hanging over his head, will Donald Trump ever be charged with a crime?

We know this: For a former U.S. president to be convicted of a crime, the prosecutor’s case must be substantial, the evidence overwhelming and the jury unbiased. The most likely scenario is that the Trump Organization will be criminally charged with a financial crime (yes, organizations themselves can be charged and criminally fined if convicted). And if the New York prosecutors have enough documentary and testimonial evidence that Donald Trump knew about those financial crimes, they would be likely to bring charges against the former president, as well.

That’s a high hurdle for them to clear. But if they don’t make it, it won’t be for lack of trying.

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