Early one morning in April, DEA and IRS agents and U.S. marshals raided several Oakland properties owned by Richard Lee, then the leading figure of California’s medical-marijuana industry. At Oaksterdam University, Lee’s multistory business school for marijuana workers, agents went in with power saws, a sledgehammer, and a small battering ram, and walked out with file drawers and bags full of loose documents. At Lee's dispensary down the block, they heaped live cannabis plants into trash bags. Word got out, and soon hundreds of protesters surrounded Oaksterdam, screaming “Fuck you, pigs!” at the officers. Some of the agitators milled around all day, hoisting signs, blocking the road, and, yes, smoking pot.

A more sober cohort also joined the protest—officials from the United Food and Commercial Workers Local 5. The UFCW had been unionizing marijuana workers since 2010, when it organized the Lee-owned businesses that were now blocked off by fluttering caution tape. At the height of the UFCW’s efforts, more than 2,000 cannabis workers, most of whom worked behind the counter selling medicinal marijuana in Western states, had signed a union contract. But federal raids have sent that figure nose-diving to 500 or so workers today. With the raid on Oaksterdam, not only had the federal government shuttered the most reputable marijuana business in the state; they had shuttered the largest union shop, of some 100 UFCW workers, in the entire cannabis industry.

“In this industry, workers are severely oppressed,” Dan Rush, the head of the UFCW’s cannabis division, said. “But it’s not by, necessarily, the employers. It’s more by an ignorant social and political environment.” And that includes the White House, he added: “A president who did not do what he said he would before he was elected.” Indeed, when Local 5 first began to organize marijuana workers, management generally refrained from interfering, in the hopes that the union would gradually help make the political environment friendlier. The understanding, one organizer said, “is that our presence would be like a sign that their businesses were legitimate and well-regulated, just like they had been telling people.” Union officials further promised to apply their political muscle to support bills and elected officials who supported decriminalizing or legalizing marijuana. The union's reward: hundreds of pot workers added to its rolls every year.

To an extent, this loose partnership has functioned well at the state level. The UFCW has been an unseen force in nearly every big push to pass marijuana-friendly laws and ordinances in Western states like California and Colorado. But federal crackdowns on pot retailers remain a constant bugbear, threatening to dry up one of the UFCW’s best streams for new membership. And while unions aren’t afraid to stare down large employers, they’re outmatched by the federal government. “We, through our international union back in D.C., are going to bend anybody’s ear who is going to listen to us about changing federal law,” said John Hughes, a cannabis division rep who works with the Local 5. “But we can’t stop the DOJ.” And when the Justice Department does come after marijuana workers, “having the union there doesn’t protect them at all.”

For a union with 1.3 million members, the elimination of 1,500 union jobs may seem negligible. It is not. New collective-bargaining restrictions, antiquated federal laws, the Great Recession, and greater hostility toward unions—by both the private sector and Republican-controlled statehouses—have collaborated to bring organized labor to its lowest membership levels since World War II. Unions have been forced to get creative, and now count victories in the low thousands, rather than the tens or hundreds of thousands. In 2012, one of the UFCW’s biggest wins was a neutrality agreement to organize around 2,000 workers at 22 Raley’s grocery stores in California. While their battle with Raley’s culminated in a nine-day strike, the UFCW has organized more than half of its weed employees after first reaching out to management, not workers. Instead of picketing sidewalks, said Matt Witemyre, who helped organize the large Oakland grower Medi-Cone, “We take [management] out to lunch. We show them our brochures, we tell them what we can do … and then we start the organizing process.”