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But when DMS -- by this time operating under the name City Sprint -- was presented with signed cards from a majority of its couriers, it was too late to call a union election. The company had declared bankruptcy, and shut its doors in July 2000.
Six months later, some bike messengers at a smaller company called Flash attempted to follow in Dedrick and Hackett's footsteps with a wildcat of their own.
The owner, a former messenger, immediately fired them all.
In 2000, messenger firms found a new way to scatter tacks on the road in front of the ILWU.
Damon Votour, the tattooed now-ex-SFBMA president, was then riding for a company called First Legal Support Services. In November 2000, the firm announced it was converting all of its messengers to independent contractors, à la Pro Mess.
First Legal employees, however, didn't even come close to qualifying as independent contractors under IRS rules. They didn't work for any other firms besides First Legal, nor did they advertise their services, set their own hours, or ask First Legal to submit bids.
As newly hatched independent contractors, they had to pay monthly dues to a Massachusetts-based company called the National Independent Contractors Association, or NICA. In return, they were told, they'd receive workers' compensation coverage and help with their soon-to-be-nightmarish taxes as "self-employed" workers.
First Legal's messengers, however, weren't happy with their new options. Especially when a little sleuthing revealed that NICA owner Thomas McGrath had pleaded guilty in 1996 and 1997 to federal charges of forging workers' comp insurance certificates for courier companies.
The ILWU promptly filed a complaint with the NLRB, in which messengers told multiple horror stories about their employer.
Votour testified that First Legal's assistant office manager, Andy Lazalde, said if he didn't sign papers to become an independent contractor, his services would no longer be needed. "And I said, 'Does that mean I'm fired?' and he said, 'Yes,'" claimed Votour.
Votour did sign, but noted on the paperwork that he was doing so "under duress and protest."
According to Votour and two other employees, First Legal's owner, Elisha Gilboa, told couriers the company could no longer afford workers' comp coverage. He allegedly added that if they didn't switch to independent status, the company would go out of business.
Asked whether the conversion was designed to trip up the union, Gilboa answered "Yes," employees testified. (Gilboa denied that in a phone interview.)
Last summer, the union won its case against First Legal. A San Francisco judge found the company guilty of numerous violations of federal labor law. The NLRB is now seeking an order forcing it to recognize the union.
The ILWU's Fred Pecker hopes the action against First Legal scares other employers out of using the same tactic to dodge the union. But so far, that hasn't happened. In December, Flash -- the company where the second wildcat strike failed so miserably -- converted its messengers to independent contractors.
Last summer, Nato Green and Carey Dall met with the ILWU's lawyers over breakfast to discuss bombarding messenger companies with another volley of wage and overtime lawsuits. The first barrage, in 1999, seemed to work well in forcing companies like Pro Mess and Speedway to the bargaining table.
In the meantime, the ILWU's headaches had gotten even worse, aggravated by another industry trend.
A number of messengers had responded to the sluggish pace of the union drive, and the lousy economy in general, by starting their own companies. Over the past five years, more than a dozen small firms like Jet Set and Godspeed have sprung up to compete with established biggies like Pro Mess. The small outfits -- managed by people whose own bike seats are still warm -- tend to be more generous with pay and benefits. One, Cupid Courier, is run as a cooperative.
Some messengers fear that over time, these little firms will grow and their owners will become just as ruthless and intransigent as those of the bigger firms. They cite the example of Flash, which was started by an ex-messenger.
"No man's absolutely good or absolutely evil. Without some kind of contract, if it's the standard hierarchical structure, then it's going to have the same boss-power relationship as the old companies," says ex-SFBMA Executive Director Bernie Corace.
But other messengers see the little firms and their more sympathetic owners as a solution to the industry's problems. And if a growing number of messengers can work for decent small firms, who needs the union?
Over breakfast, the ILWU legal eagles warned Green and Dall that not only were wage and OT lawsuits costly to the union, but they might even trigger the collapse of some financially shaky firms, says Green. Obviously, that would mean fewer jobs for messengers -- and fewer members for the ILWU.
Green and Dall later reconvened over barbecued brisket at a Lower Haight restaurant. There they hit on a different strategy. They decided to file wage and OT claims with the California Labor Commission instead. Let the state pick up the tab for actually suing the companies. And if the firms couldn't afford to pay, screw 'em.