Photograph by Alex Wong/Getty

Michael Grimm’s pugnacious career in government service ended with a whimper on Monday night, with an after-hours statement announcing his resignation from Congress. It had been a week since Grimm, the Republican congressman from Staten Island, pleaded guilty to one charge in a twenty-count federal indictment for tax fraud and perjury. Outside the courthouse that day, he declared that he had no plans to step down. It was easy to imagine that Grimm would keep his word, if only because of the sheer volume of allegations that the congressman had already beaten back—including those recounted here in 2011, in which Grimm, while serving as an F.B.I. agent, was alleged to have pulled his gun in a Queen’s night club and instigated a racially charged incident (acts that he denied).

But step down he did, bringing an end to a congressional tenure consisting of equal parts bluster and farce. Grimm will probably be best remembered for his on-camera threat to throw a NY1 television reporter off of the Capitol Rotunda balcony after he’d dared to ask a question about the Justice Department investigation into Grimm’s fundraising. And no collection of Grimm’s greatest hits can leave out the interview in which he recited almost verbatim a speech from “A Few Good Men” as if it were his own. The Grimmest of Grimm moments occurred, however, during his 2012 campaign, when he publicly insinuated that political forces arrayed against him had broken into his office to gain access to computer files. The break-in turned out to be the work of a troubled teen-ager. The computers, police concluded, hadn’t been touched.

Grimm previously worked as an undercover F.B.I. agent, and he cited that fact repeatedly on the campaign trail—at one point drawing a rebuke from the bureau. In November, he won reëlection in the shadow of his federal indictment and a potential trial. While some Democrats accused him of shamefully holding his guilty plea until after Election Day, he may have done his constituents a favor by saving them from an opponent so inept that he earned more mockery than even the congressman himself. (“In Domenic Recchia, the Democrats have fielded a candidate so dumb, ill-informed, evasive and inarticulate that voting for a thuggish Republican who could wind up in a prison jumpsuit starts to make rational sense,” the Daily News observed in one of the most comically underwhelming endorsements ever published.) Now each party will have a new chance to field a less-bad-than-the-other-guy candidate in a special election.

Ultimately, though, Grimm’s plea and resignation will prove unsatisfying to anyone but political partisans. He has admitted to paying undocumented workers under the table as the owner of a Manhattan restaurant called Healthalicious, filing false tax returns to profit from it, and then lying about all of it to investigators. These are not trivialities, but the public will likely never obtain answers to more serious questions around Grimm’s conduct as an elected representative. In 2012, the Times reported extensively on hundreds of thousands of dollars Grimm raised from the followers of the New York City rabbi Yoshiyahu Yosef Pinto, detailing allegations that Grimm advised contributors on how to exceed legal limits and that he collected donations in envelopes full of cash. (Pinto, in an absurdly complicated investigation spanning New York and Israel, later reportedly accused Grimm of blackmailing him.) By 2014, a federal investigation was underway, and one of Grimm’s campaign contributors (and former girlfriend), Diana Durand, was soon under indictment for using straw donors to exceed contribution limits. The U.S. Attorney’s office had assigned Assistant U.S. Attorney Todd Kaminsky, known for his success in public-corruption prosecutions, to Grimm’s investigation. But Kaminsky left the case in May to run for state assembly, Durand pleaded guilty without implicating Grimm, and no campaign-finance charges were ever brought against the congressman.

Federal prosecutors were left with the Healthalicious tax fraud, which, depending on one’s political affiliation, came off as either Capone-like in its catch-them-for-what-you-can-prove approach or evidence of the “political witch hunt” Grimm had invoked against the allegations all along.

Grimm has long made a habit of leaving such problematic connections in his wake, and then chalking up any accusations of impropriety to conspiracy. I first became interested in him while investigating one of his F.B.I. informants, a scam artist named Josef von Habsburg who helped lure a lawyer into a dubious sting operation. “I am an F.B.I. agent, I took an oath,” the then aspiring congressman railed at me when I asked him questions about his F.B.I. past, including the night-club incident. “You’re trying to do a chop job on me.” When I asked him why he left the F.B.I. when he did, just after having helped build a large and successful case against fraud on Wall Street, he said, “I was really at the top of my career. If I was gonna leave, leave at the top.” Later, the Times reported on Grimm’s post-F.B.I. business ties to a convicted fraudster and former F.B.I. agent in Texas, along with the campaign-finance questions and the allegations that Grimm’s partner in Healthalicious had connections to the Gambino crime family. “This attack is politically motivated,” Grimm responded.

Federal prosecutors have not made clear whether any of their investigations remain open. One former Assistant U.S. Attorney with whom I spoke—who did not have direct knowledge of the case—found it unlikely that Grimm would have taken any plea deal that didn’t include at least tacit agreement from prosecutors to no longer pursue such charges.

Grimm now faces a federal prison sentence of up to thirty-six months. Whether he ends up alongside the convicts he once took great pride in cornering will be left to U.S. District Court Judge Pamela Chen. What we do know is that Michael Grimm is a man who betrayed the laws he once made such a show of upholding.