The media commentary that followed the surprising (to me, and to many others) August 7th federal extortion conviction of Kenneth Brissette and Timothy Sullivan, senior aides to Boston Mayor Marty Walsh, misses the point as to why this verdict, and the prosecution that culminated in this result, are so dangerous to civil society and, not so incidentally, to all of our civil liberties.

The federal extortion statute suffers from a vagueness problem, such that it is impossible to discern a clear line between illegal pressure to obtain what is not due you, and perfectly lawful pressure that a labor union and its allies may (and very often do) exert on a recalcitrant non-union or anti-union employer. In the absence of such a line, labor union officials and their political allies, including the likes of Brissette, Sullivan and Walsh, risk indictment while performing rather ordinary political tasks.

In other words, this indictment and especially the conviction place intimidating power in the hands of federal prosecutors and consequently can deter elected officials from performing the duties that those who elected them have a right to expect. Walsh, a former labor union official who was elected with strong labor support, was obviously going to be a pro-labor, rather than a pro-management, mayor.

Some background is necessary.

After U.S. District Judge Leo Sorokin in March of 2018 dismissed the indictment on the ground that Brissette and Sullivan’s conduct did not amount to criminal extortion, the prosecutors, rather than drop the case as hopelessly flawed, instead appealed to the Court of Appeals for the First Circuit. The First Circuit, less perspicacious than Judge Sorokin, and to my own considerable surprise, reinstated the charges a year later, and Lelling’s office took another swing at bat. Now, five months later, the jury unanimously voted to convict. Brissette and Sullivan’s lawyers are planning to ask Judge Sorokin to throw out the jury’s verdict and acquit the defendants – an action that, if taken by the judge, would be appealable by the feds to the First Circuit.

Eventually, the case could make its way to the Supreme Court. Even though the nation’s highest court accepts for appellate review only a small percentage of the cases presented to it – about 5% – this case would have a better-than-average chance of being taken up. Why? Because for well over a decade now, the Supreme Court has demonstrated its intent to reel in wide-ranging prosecutions brought by overzealous prosecutors who, armed with vague and broad federal anticorruption statutes, seek to criminalize the familiar give-and-take of ordinary politics.

The Supreme Court in June 2016 unanimously threw out the federal corruption conviction of former Virginia Governor Bob McDonnell, ruling that the extortion statute was not meant to criminalize routine political behavior. Governor McDonnell’s conduct might have been tawdry – he gave “access” to a mogul who showered gifts on McDonnell and his wife—but the mogul did not end up with the lucrative contract he sought. Tawdry conduct, the justices said, does not equal criminal conduct.

McDonnell followed the 2010 high court‘s decision in Citizens United v. Federal Election Commission, the case that threw out certain campaign finance limitations on the ground that, far from signifying corruption, the campaign finance system—where donors could richly finance a candidate of their choice—benefited from First Amendment protection. Donors’ money may amplify and support political choices. Again, certain aspects of the raw game of politics might not always be pretty, but this does not equal criminal conduct.

That same year, the Supreme Court reversed the conviction of former Enron executive Jeffrey K. Skilling, ruling that federal anticorruption statutes criminalizing the deprivation of the citizenry of the “honest services” of public officials could be applied only to core bribes and kickbacks. The high court said that “ingratiation and access,” so common in politics, do not equal corruption.

Thus, the Supreme Court has made patently clear, in this series of incremental decisions, its intent to narrow the vague and broad federal anticorruption statutes that make possible—and indeed almost invite—wide-ranging prosecutions of political figures brought by overzealous prosecutors who seek to classify routine political behavior as “extortion.” The Boston Calling situation falls cleanly within this description.

The case, it will be remembered by those who have managed to navigate its twists and turns, centered around complaints that mayoral aides Brissette and Sullivan pressured the organizers of the Boston Calling Music Festival into hiring union labor. After Brissette and Sullivan learned that members of the International Alliance of Theatrical Stage Workers Local 11 were upset with the non-union status of the project, the pair, working for a pro-union mayor who himself worked for organized labor before being elected the city’s chief executive, tried to mollify the union workers by pressuring the festival organizer, Crash Line Productions, into hiring a few union members to join the crew.

To the feds, this constituted the crime of extortion – using official pressure and threats to get the recipients of city permits to pay something of value in order to obtain those permits.

The problem with the prosecution’s theory, however, was that there was never any suggestion by Lelling or anyone else that either Brissette or Sullivan, much less Mayor Walsh, had demanded or received any money for themselves in exchange for awarding the necessary permits to the music festival organizers. Any pressure exerted was for the purpose of mollifying the labor union that was threatening to picket at City Hall Plaza with a large inflatable rat – the symbol long employed by labor unions to signify non-unionized strikebreakers. No mayor in Walsh’s shoes would be pleased by such an embarrassing scenario, and Brissette and Sullivan well knew the man for whom they worked – a former labor organizer.

In light of the facts, one is left wondering, “Crime? Or politics as usual?” If the question is reasonably asked, that alone is indication enough that the case for “extortion” is probably weak-to-nonexistent and cannot be proven to a jury “beyond a reasonable doubt” (the standard for jury findings of guilt in criminal trials).

It would be easy to think that this ill-considered prosecution was a product of the anti-labor animus of a conservative Republican administration in Washington. However, that’s simply not the case. The prosecution was initiated during the liberal Democratic Obama Administration when Carmen Ortiz was the United States Attorney.

After President Trump was elected, his pick for the top federal prosecutorial post in Massachusetts grabbed the baton from Ortiz and ran with it.

What this tells us, and what I’ve been arguing for decades, is that federal prosecutors use, and often abuse, their power not because they are either Republicans or Democrats, but rather because the Department of Justice is its own powerful fiefdom that uses and abuses its institutional power to terrorize civil society. Power, not politics, is the key to understanding these dubious prosecutions.

It was the rule of law that lost in the Boston Calling trial, not any particular political party. However, on appeal, justice might well prevail if the Court of Appeals takes the broad hints that the Supreme Court has been trying to convey for years – that the exertion of political pressure does not equal the crime of extortion. If the First Circuit does not do its duty, the Supreme Court might well accept the case for review. One way or the other, these two convictions are unlikely to stand.

Harvey Silverglate, the WGBH News Freedom Watch columnist, is a Boston criminal defense lawyer and civil libertarian who practices at the Boston firm Zalkind, Duncan & Bernstein LLP. He is the author, most recently, of "Three Felonies a Day: How the Feds Target the Innocent" (2011). Paralegal Monika Greco assisted in research and editing.