The Teamsters union just drew a fresh line in the sand with UPS. At its international convention in Las Vegas this month, delegates passed a resolution with zero opposition. It orders union leaders to go after the package giant for steering work to nonunion gig drivers through its Roadie subsidiary. The move isn’t isolated. It caps years of friction since the landmark 2023 contract that delivered big wage gains but left room for endless disputes over enforcement.
UPS employs roughly 330,000 Teamsters, including some 100,000 drivers. The union says the company has spent the past four years expanding Roadie operations across the country. Dozens of distribution centers and cross-docks have appeared. And the app that connects gig workers to same-day retail deliveries keeps growing. Teamsters call it a direct threat to their jobs. They point to UPS labels, tracking numbers and equipment showing up on Roadie runs. To them, that proves the work belongs in union hands.
Grievances Pile Up as Union Flexes Muscle
But the Roadie fight sits inside a larger pattern. The union has filed grievances and even lawsuits claiming UPS repeatedly sidesteps the 2023 National Master Agreement. Last February the Teamsters went to federal court in Massachusetts. They sought an emergency restraining order to block UPS’s Driver Choice Program, a buyout offer the union labeled illegal. Court filings listed at least six contract violations. Direct dealing with workers. Cutting union jobs despite promises to add positions. Undermining shop stewards’ rights. The list went on. Sean M. O’Brien, Teamsters general president, didn’t mince words. “For the second time in six months, UPS has proven it doesn’t care about the law, has no respect for its contract with the Teamsters, and is determined to try to screw our members out of their hard-earned money.”
Fred Zuckerman, general secretary-treasurer, called the program an assault on the rule of law itself. He warned that letting it proceed would inflict irrevocable harm on the union and its members. The Driver Choice Program offered lump-sum payments in exchange for drivers agreeing never to work for UPS again. They would waive union representation and forfeit future wages, health coverage and pensions. It looked a lot like the earlier Driver Voluntary Separation Program that many drivers had already rejected. Local unions filed grievances. Arbitration loomed.
Pressure worked. By April, UPS and the Teamsters reached a settlement. The company capped severance offers at 7,500 drivers nationwide. Eligible long-haul feeder and regular package car drivers could take $150,000 for early retirement, with offers based on seniority. UPS agreed not to launch any other severance programs for the rest of the contract, which runs through July 31, 2028. Seniority rights stayed protected. O’Brien claimed victory. “UPS never had the contractual right to unilaterally offer driver buyouts, but with enough pressure and member solidarity, UPS finally did the right thing by putting its commitments to hardworking Teamsters down in writing.” (Teamsters.org, April 5, 2026)
The Roadie battle carries a different flavor. It centers on outsourcing. The 2023 contract, according to the union, bars UPS from handing off tasks that belong exclusively to union members to gig operators. In November the union went public with complaints. Roadie, they said, was pulling packages that should travel through the main UPS network. A national Roadie Committee formed to gather evidence from members. They mapped facilities. They collected stories. The convention resolution now gives top leadership marching orders to press grievances and force compliance. (Yahoo Finance, June 18, 2026)
UPS pushes back. The company insists it follows the contract for its small-package business. All such deliveries, it says, go through union drivers. Disputes belong in the grievance system that has operated for years. Roadie, executives note, focuses on same-day urgent shipments from stores. Groceries. Oversize items. Orders from Walmart, Tractor Supply or Benjamin Moore that never touch the main sortation hubs. Those loads, UPS maintains, fall outside the core agreement. Yet the union sees a slippery slope. Every package diverted weakens the bargaining power built over decades.
And the tension shows no sign of easing. Recent social media from the convention captured rank-and-file UPS Teamsters taking the stage. They spoke of victories won in 2023. They listed priorities for the next round of talks. Air-conditioned trucks. Full-time job conversions. An end to what they call overtime abuse. The union has already sent formal requests for information on heat protections, staffing levels and open grievances. Volume may be softer than peak years, but UPS still reports solid profits. The company cut thousands of managers after the last contract. That fact hasn’t gone unnoticed among drivers who remember the strike threat that produced their record deal.
So the grievances keep coming. The lawsuits test the limits. Settlements get negotiated under duress. Each episode reveals the same underlying contest. UPS wants flexibility to reconfigure its network and control costs in a competitive market that now includes Amazon and a swarm of gig platforms. The Teamsters want every piece of work that fits the contract to stay inside the union fold. They remember how close they came to a nationwide strike in 2023. That memory fuels their current push.
Recent coverage shows the fight remains active. A FreightWaves report echoed the Yahoo Finance story, noting the convention resolution and the union’s determination to reclaim outsourced work. No new settlement on Roadie has surfaced. The grievances are still moving through the system. Arbitrators will have their say. But the message from Las Vegas was unmistakable. The union that forced UPS to the table once stands ready to do it again. Member solidarity, the delegates believe, remains their strongest card.
UPS, for its part, continues to reconfigure operations. It highlights employee interest in the earlier buyout offers. It points to the settlement as proof that dialogue works. Yet the pattern suggests dialogue alone won’t settle every difference. The 2023 contract runs another two years. Plenty of time for more grievances. More resolutions. And, if needed, more pressure on the streets.
WebProNews is an iEntry Publication