Donald Trump has disbanded his manufacturing advisory council, most likely to avoid more defections in the wake of his noxious remarks about white supremacist violence in Charlottesville, Virginia. Among the many members to resign in the days leading up to Trump’s decision was AFL-CIO president Richard Trumka.

Trumka publicly rebuked the president for his comments, but his departure caused a smaller rupture in the group than when a pharmaceutical executive left, raising Trump’s public ire. If anything, Trumka’s resignation only evoked the obvious question: what was the nation’s highest labor official doing on a board of industrialists, advising a president with a litany of odious campaign promises?

On the labor front alone, Trump’s presidency has already been disastrous. His decision to appoint Neil Gorsuch to the Supreme Court, giving conservatives a five-four majority, all but assures that the public sector will become “right-to-work.” His appointments to the National Labor Relations Board will likely roll back the limited gains labor made under President Obama. His secretary of education, Betsy DeVos, continues to rankle teacher union leaders.

Trumka knows there are union members who do like Trump — nearly half of voters from union households went for him. But why would Trumka stand with this half rather than the other?

To answer that, we have to roll back the clock a year, to September 2016, when Sean McGarvey, the president of the Building and Construction Trades, wrote a letter to Trumka voicing frustration with several AFL-CIO affiliates — the Amalgamated Transit Union, National Nurses United (NNU), the American Postal Workers Union, and the Communications Workers of America — who supported the Standing Rock protests.

McGarvey’s gripe wasn’t just that the anti-pipeline resistance was threatening jobs for his members, but that the union leaders were aligning themselves with dangerous extremists. Redbaiting aside, McGarvey’s implicit warning was that if Trumka didn’t show his support for the building and constructions caucus, some of its affiliates might bail on the national federation altogether — leaving it in an even direr, cash-starved state.

Then came Trump’s election. Immediately Trumka sought to find common ground with the new president, somehow looking past his unabashed bigotry and leadership of a party fiercely hostile to organized labor. For Trumka, it was enough that Trump vowed to renegotiate NAFTA and pass sweeping new infrastructural projects.

The week before Trump’s inauguration, Trumka traveled to Trump Tower to speak with the incoming president (according to Trumka, the then–president elect promised vast spending on roads and bridges). Later that month, Trump held a very public White House meeting with representatives from various building trades unions. “We have a common bond with the president,” McGarvey said afterward.

Meanwhile, the rest of the labor movement joined the broader left in opposing the administration. The American Federation of Government Employees has fought regressive changes in federal employment (most recently blasting Trump’s attempts to remove protections against discrimination based on sexual orientation). SEIU affiliates continue to oppose Trump’s draconian immigration measures. And NNU has been a stalwart voice on health care, standing against Obamacare repeal and pushing for Medicare for All.

While Trumka lodged his own criticisms at Trump, he remained on the advisory council, apparently out of a belief that since infrastructure and transport can’t be offshored (and since there’s no current legal threat to their existence), the building trades would be the last remnant of labor power. In other words, he placed his bet on a closed group of skilled-trades manufacturers and construction workers tied to the president’s pet projects — most of which probably won’t happen anyway — as public sector unions, vehicles for upward mobility for non-whites and women, face virtual extinction.

The whole ordeal has revealed a few things. First and foremost, Trumka’s incredible naiveté. How could he think there was any way to win concessions from a fundamentally reactionary administration? That Trump, a billionaire magnate, could open up opportunities for union growth?

Second, it’s shown the profound limitations of trying to appease the building trades at the national level. Trumka got a seat at the table with capitalists and with the president. And nothing went anywhere. In a sense, Trumka is worse off with the building trades than before — not to mention the progressive movement. He made a big show of joining the council and got nothing. In the wake of Charlottesville, he’s tried come off as disgusted with the president’s stance, but his message was lost. If he tries now to become an opposition figure, as someone who wants to vigorously fight Trump’s immigration and health care agenda, it could be easily be viewed as too little too late.

Above all, the episode is a reminder that when labor leaders try to work with business leaders and conservative politicians, it’s a gamble rigged in the house’s favor. Only an addict would keep playing.