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One need not be a supporter of former President Donald Trump — and I assuredly am not — to have serious qualms over his apparently imminent indictment in New York City for the covert payment of hush-money to porn star Stormy Daniels during the latter days of the 2016 presidential campaign.

Trump has derided the inquiry and looming criminal charges as a "racist" and "political" undertaking by Manhattan District Attorney Alvin Bragg, a Black Democrat, while many Republicans, including congressional leadership and prospective GOP rival Florida Gov. Ron DeSantis, are echoing the complaint about political motives.

Less partisan observers have noted the legal flaws in the case. They include the expired statute of limitations (unless circumvented due to Trump's absence from the state); the somewhat convoluted legal theories involving an intersection of state business records laws, federal election campaign regulations, and allegations of tax evasion. And then there are the seedy characters upon whom the case rests, the former lawyer-fixer Michael Cohen — a convicted federal offender — and Daniels herself. These deficiencies, among others, cast a shadow on the prospective proceeding.

But there's another reason why the case may be fraught with folly. It relates to another high-profile celebrity criminal defendant of recent years: Bill Cosby.

The breakthrough Black performer of the late 1960s — stand-up comedian, variety show host and hugely popular family-comedy television star — was criminally charged and ultimately convicted in 2018 in a Pennsylvania state court of sexual assault after his first trial ended in a hung jury.

A candidate for the elected position of state prosecutor had campaigned on a pledge to initiate a new case against Cosby after the initial hung jury put the proceedings in limbo. That candidate won and oversaw the second successful prosecution, which resulted in a prison sentence of up to 10 years for the then 80-year-old fallen superstar, ailing and nearly blind.

But the conviction was subsequently reversed by the Pennsylvania Supreme Court in 2021, resulting in Cosby's release after three years and dismissal of the charges against him.

The reversal of Cosby's conviction did not turn on the prosecutor's campaign promise to pursue the case. Rather, the verdict was thrown out because a previous prosecutor had promised Cosby and his counsel that he would not pursue criminal charges if Cosby would subject himself to a deposition in his accuser's lawsuit. He did, leading to a $3.4 million out-of-court settlement of that litigation, preceding a number of additional large settlements and one jury verdict favorable to other women who had accused Cosby.

The prosecutor's campaign promise to convict Cosby is where the Cosby and Trump cases intersect. Manhattan prosecutor Bragg was elected in 2020, the same election cycle that ousted Trump from the White House. A defining issue in the New York City district attorney campaign that year was whether to seek charges against Trump. Bragg took the most aggressive stance, paving his way to a decisive victory.

While the reversal of the Cosby verdict did not turn on the impropriety of the Pennsylvania prosecutor's campaign pledge to pursue a criminal case against a specific named individual, it formed a sinister underlying sinkhole for the prosecution. The same flaw could taint Bragg's pursuit of the hush-money case in New York City.

The political pledges to pursue Cosby and Trump evoke consideration of a hoary legal doctrine known as bill of attainder. The term refers to a practice of pre-Revolutionary War authorities in England, who passed laws specifically targeting identified individuals or groups.

The framers of the U.S. Constitution reviled that despotic practice and explicitly proscribed it twice in the nation's fundamental law. Article I, Section 9 prohibits enactment of any bill of attainder by Congress and the ensuing Section 10 forbids states from doing so, either.

The double prohibition expresses the Constitution's strong antipathy to the singling out of particular individuals or entities for criminal prosecution. The American tradition is instead to proscribe particular conduct, rather than targeting a specific offender.

But Bragg's naming of Trump in a political campaign as a specific target of criminal inquiry is akin to an impermissible bill of attainder. While not the product of legislation, the outcome is the same: condemnation of a particular defendant before a specific accusation of wrongdoing has been investigated by law enforcement personnel.

By bragging about his intent to pursue criminal charges against the ex-president in order to be elected, the Manhattan DA may have tainted that proceeding much as the injudicious campaign rhetoric of the Pennsylvania prosecutor helped undermine the Cosby case.

Marshall H. Tanick is a Twin Cities constitutional law attorney.