Dingell felt obliged to quit the NRA's board in 1994, when he voted for President Clinton's omnibus crime bill despite the fact that it included a ban on assault weapons that Dingell and the NRA strongly opposed. But he was back in line with the organization in 1999, when it appeared that the uproar over the massacre at Columbine High School in Littleton, Colorado might finally provide the momentum to close the “gun-show loophole,” which exempts unlicensed dealers at gun shows from having to perform background checks on gun buyers. The Senate voted to close the loophole, with Vice President Al Gore providing the tie-breaking vote. But before the House had the chance to follow suit, Dingell, the chairman of the powerful Energy and Commerce Committee, intervened with an alternative proposal supported by the NRA. It would close the loophole for unlicensed dealers–but weaken the background check, by reducing the amount of time authorities would have to perform it from 72 to 24 hours, while also limiting the definition of events considered actual “gun shows.”

It was a brilliant gambit. The alternate proposal divided supporters of expanded background checks, with some arguing for accepting the weakened checks and others arguing they had been rendered all but meaningless—24 hours was inadequate given how hard it was for the authorities to track down paper records, not to mention that many gun shows are on weekends. Meanwhile, Dingell’s proposal gave cover to members who were reluctant to oppose the NRA, allowing them to say they had voted “for expanded background checks.” Dingell’s amendment passed on a 218 to 211 vote, while the measure that had passed the Senate failed by a 235 to 193 vote. The water sufficiently muddied and gun control supporters divided over how to proceed, the push to close the loophole faltered.

Then, in 2007, after yet another classroom massacre—at Virginia Tech—Dingell once again intervened on the NRA’s behalf to bend in its direction even the exceedingly moderate legislation being considered at the time, to encourage states to do a better job of including records of those deemed dangerously mentally unfit in the database for gun background checks. (The Virginia Tech shooter’s mental health adjudication had not been reported to the database.) At Dingell’s behest, the law’s funding to help states improve their records was dependent on their allowing those barred from owning firearms, including convicted felons, to petition for restoration of their gun rights. The resulting provision was so poorly worded that some states have refused to accept the funding to improve their records, while in some of those that have—including Virginia!—restoration of gun rights has been disconcertingly loosely supervised.

More recently, there have been signs of daylight between Dingell and the NRA—in 2012, he opposed an NRA-backed vote holding Attorney General Eric Holder in contempt over the “Fast and Furious” gun-walking operation, which was linked to the Arizona shooting death of a border control agent from Dingell’s district; Dingell deemed it “clearly not a Second Amendment issue” despite the NRA’s agitation over the issue. And after the Newtown, Conn. massacre in 2012, gun control advocates saw hopeful signs that Dingell wouldn’t stand in the way of sensible reform. But Dingell never had the chance to vote on expanded background checks, which this time around never made it out of the Senate—as they had back in 1999 when his connivance managed to undermine them.