The tower of aging Manila envelopes, stacked in a corner of Rome Aloise’s cluttered Bay Area home office, is a monument to five years of failure. Aloise, who heads the Northern California chapter of the Teamsters union, has spent a lot of time sitting across a table from officials at Uber and Lyft, trying to work out a deal to organize their drivers. The companies wanted to forge peace with labor while ensuring the workers would still be considered independent contractors without the legal rights employees are guaranteed, including the hourly minimum wage. The union wanted to increase its ranks and boost drivers’ pay without setting a precedent that would endanger its other members’ rights. The envelopes contain a small forest’s worth of rejected proposals, handwritten notes, and other detritus from a great many meetings that couldn’t bridge the gap. “Everybody would love to see some resolution,” Aloise says. “It’s just what that looks like is the problem.”
Back and forth the companies and the Teamsters have gone over the years, as the firmament has shifted around them. During Aloise’s first round of monthslong talks at Uber Technologies Inc.’s headquarters in San Francisco, in 2016, the company’s clout was on the rise—its top officials included then-President Barack Obama’s former campaign manager, and Obama himself joked about becoming an Uber driver after leaving the White House. A couple of years into the Trump era, the union appeared to have the upper hand, after California judges and legislators made it much tougher to call workers contractors if they were central to a company’s operations. Now, however, union leverage is at a nadir, and the scenario that labor officials—including some who don’t represent drivers—spent years trying to head off is beginning to unfold.