Teamsters General President Sean O’Brien has told union members he expects an eventual strike against UPS when the current five-year national contract expires on July 31, 2028, according to a September 10, 2026 report by FreightWaves based on his comments across a series of union podcast appearances and public events. “It’s going to be a battle and we are probably going to strike UPS,” O’Brien said. “I am not optimistic of coming to a tentative agreement without striking UPS.”
What the current contract already delivered
The agreement now in force, ratified in 2023, is valued at $30 billion and covers roughly 330,000 UPS Teamsters nationwide. It delivered a $2.75-an-hour raise in its first year, ended the two-tier wage structure for delivery drivers, and made 60 changes to working conditions. Part-time workers — historically UPS’s lowest-paid group — have since seen starting pay rise to $21 an hour, climbing to $23 an hour for those who advance. O’Brien said senior full-time drivers now earn about $170,000 a year in combined wages and benefits, a figure the union points to as proof the 2023 deal was real money, not just a headline number.
| Detail | Figure |
|---|---|
| Current contract value | $30 billion |
| Workers covered | ~330,000 UPS Teamsters |
| Contract expires | July 31, 2028 |
| First-year raise (2023) | $2.75/hour |
| Part-time starting pay | $21/hour, up to $23/hour |
| Senior driver pay | ~$170,000/year, wages and benefits |
| UPS 2025 revenue | $88.7 billion |
| UPS 2025 stock buybacks | $1 billion |
What the union is fighting to protect next
O’Brien laid out four priorities for the 2028 round of bargaining: blocking any rollback to health and pension benefits, limiting automation and autonomous-vehicle deployment inside UPS’s delivery network, stopping outsourcing through UPS-owned subsidiaries such as Roadie and Happy Returns, and winning the right to strike mid-contract over unresolved grievances in every region — a right Teamsters in the union’s Central Region already have. UPS reported $88.7 billion in revenue in 2025 and returned $1 billion to shareholders through stock buybacks that same year, numbers O’Brien has pointed to as evidence the company can afford to hold the line on benefits rather than trim them at the table.
Part of a pattern in 2026
The UPS fight is still two years out, but it lands in a year when organized labor has already shown it will use its leverage. Teamsters mechanics at Frontier Airlines just ratified a five-year deal by a 93% vote, the union’s Central States pension fund climbed to roughly 98% funded after a federal rescue, and UPS Teamsters’ existing contract-guaranteed cost-of-living clause has kept delivering raises through 2026. Each of those results came out of a specific contract, negotiated at a specific moment — not a guarantee that carries automatically into the next one.
What stays with the job, and what doesn’t
UPS Teamsters have the largest and best-funded private-sector union contract in the country, and O’Brien’s own warning is that even it gets renegotiated — and re-fought — every few years. Pension contributions, health coverage, and job protections that look secure today are bargaining chips the next time the contract comes up, and none of it is guaranteed to survive intact once automation, outsourcing, and profit pressure enter the room.
A whole life or final expense policy that a UPS worker owns individually, separate from the union’s welfare and pension funds, doesn’t depend on how the next round of bargaining goes. It keeps its death benefit and cash value intact through a strike, a job change, an automation-driven route cut, or retirement — coverage that travels with the worker rather than staying behind with the contract.
For Teamsters and other union members weighing their own coverage, our union members coverage page, whole life and final expense pages, and free calculator are good starting points.
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Frequently Asked Questions
Is a UPS strike actually happening in 2028?
Not yet — no strike has been called and formal negotiations have not begun. Teamsters General President Sean O’Brien said in a September 2026 report that he expects an eventual strike when the union’s current national contract with UPS expires on July 31, 2028.
What does the Teamsters union want from UPS in the next contract?
O’Brien named four priorities: protecting pension and health benefits from rollbacks, limiting automation and autonomous-vehicle deployment, stopping outsourcing through UPS subsidiaries such as Roadie and Happy Returns, and winning the right to strike mid-contract over unresolved grievances in every region.
Why does a future UPS contract fight matter for a worker’s own life insurance?
Pension and health benefits negotiated into a union contract apply only as long as that contract holds and the worker stays covered by it. An individually owned whole life or final expense policy sits outside any employer or union plan, so it keeps its value regardless of how a future strike, contract, or job change turns out.
Coverage that stays with you, not the contract
A licensed United Trust Life agent can help Teamsters and other union families find final expense or whole life coverage that travels with them — free, and no pressure.
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