The Union That Can’t Escape Itself: The Unfinished Story of the Teamsters

It is fairly certain that the International Brotherhood of Teamsters is the most famous, or rather the most infamous, union in the United States. While one can hope the first thing that comes to mind when the Teamsters come up is trucking, it is just as likely thoughts turn to Jimmy Hoffa and his unsolved murder, Las Vegas, the Mafia, etc. Martin Scorsese made quite a bit of hay on such matters in films like Casino and The Irishman. Hoffa himself will go down as the only figure to be portrayed by both Jack Nicholson (Hoffa) and Al Pacino (The Irishman). 

If all that is firmly entrenched in popular culture, Joe Allen’s new book Teamsterland: Reports on America’s Most Iconic Union touches on plenty more. The book features a compilation of pieces Allen wrote for various publications from 2019 to early 2025 and inside we’re reminded of the Teamsters’ undermining of Cesar Chavez’s United Fruit Workers and the union’s longtime and early support for Israel, among other things. 

Then there is the actual business of organizing and running a union. While hauling freight in trucks is probably still what the Teamsters are most known for, that largely went away when the trucking industry was deregulated in the late-1970s. The union now represents workers across the economy in sectors from warehousing to food processing (membership peaked at 2 million in 1976, now it sits at 1.4 million). For a while even the roughly 300 horse-drawn carriage drivers in Central Park who skillfully convince tourists to part with large amounts of money for 20-minute rides were under the Teamster banner. 

But the main thing now is package delivery to homes and United Parcel Service (UPS) is the largest Teamster employer in the U.S. as well as the largest unionized employer in the U.S. As Allen explains, many Teamster locals wouldn’t exist without UPS and the union as a whole would be ‘a ramshackle collection of old freight companies and local employers with little national clout.’ 

The union seems to live in endless contradiction. Back during the pandemic Bloomberg ran a story with the headline ‘Highly paid Union Workers Give UPS a Surprise Win in Delivery Wars.’ The article described how UPS was outperforming its nonunionized counterpart FedEx by meeting the delivery deadline for 95 percent of its packages, as opposed to FedEx’s 85 percent- proving again that an organized workforce gets the job done. Yet that same year NBC News reported at least 107 UPS workers in 23 states had been hospitalized since 2015 for heat illness due to lack of air conditioning in UPS trucks. Yet Teamster leadership was slow to make demands. The latest contract, agreed to in 2023, requires the company to equip its fleet with at least 28,000 new air-conditioned trucks by the time the contract expires in 2028 (that’s roughly a third of the fleet). According to new reports, few appear to have been purchased so far.

As Allen points out, the Teamsters are one of the few major unions that have membership directly elects the top offices. Yet membership turnout has long been on the decline, crashing to 15 percent in 2016 when longtime incumbent James P. Hoffa (son of the Jimmy Hoffa) was nearly defeated. This Hoffa would serve 24 years as union president. When membership voted down a proposed contract and supplements in 2018, Hoffa used an obscure clause in the Teamster Constitution originating in 1940 to declare the contract passed. 

Reform movements within the union bubble up only to fizzle out or be co-opted. In fact, the current president, Sean O’Brien, came out of the longtime Teamsters for a Democratic Union (TDU) faction. He has spent some of his days in office hobnobbing with the likes of Trump and Josh Hawley. O’Brien even spoke at the Republican National Convention in the lead-up to the 2024 election. 

Teamsterland chronicles a period that can be described as both eventful and ultimately uneventful. Besides the election of O’Brien, there was the drama around a national strike against UPS in the summer of 2023 and the long overdue, and thus far fruitless, fight to organize Amazon. 

The last national strike took place in August 1997 under the leadership of Ron Carey. At that time 180,000 workers hit the picket lines for three weeks under the banner ‘Part Time America Won’t Work.’ Allen explains it was the most important industrial struggle in a generation and the strike was victorious. The result was a pay raise, the creation of full-time jobs from part-time positions, and the maintenance of the union pension that UPS wanted to get out of and offer its own company plan. 

However, in the aftermath of the strike Carey was forced out. Allen puts it like this: 

However, in the weeks and months that followed the strike, the combination of a witch-hunt atmosphere created by the Republican-controlled Congress and criminal investigations by President Clinton’s Department of Justice successfully ousted Ron Carey from leadership of the Teamsters, and eventually expelled him from the union. This government sponsored counter-reform coup was a big factor in bringing Hoffa to power for two decades…UPS won on the political battlefield what it couldn’t win on the picket line. The wider potential of the strike, such as organizing FedEx- a virtual twin of UPS and the natural next step in organizing the burgeoning non-union logistics industry of the 1990s, was thwarted. 

It appeared conditions were in place for a possible national strike in the summer of 2023. New leadership was in place, the previous contract had been voted down by membership, SAG-AFTRA was shutting down Hollywood while UAW was leading a successful strike against the car companies. That June, leadership announced that locals representing UPS workers would begin conducting strike votes. Yet the affair ended in a whimper as the union ended up agreeing to a contract that the Wall Street Journal described as win for the company. The contract preserved low pay for new part-time hires and according to WSJ ‘greater flexibility in work schedules and new technology.’

As for Amazon, in 2024 the Amazon Labor Union (ALU) voted to affiliate with the Teamsters. ALU, which successfully won a vote in New York City in 2022, the first successful vote in an Amazon fulfillment center, in the vote that made Christopher Smalls a national sensation, has been stuck the past couple of years. The union lost four subsequent votes at other fulfillment centers and hasn’t been able to get recognition or a contract off Amazon in New York. The affiliation with the Teamsters is meant to bring financial and organizational muscle. 

Last December the Teamsters did attempt to stage something of a five-day strike at eight Amazon locations across four states. However, though the union labeled it ‘the largest strike against Amazon in U.S. history’ it had basically no effect on Amazon’s operations as only roughly six hundred workers took part. Allen points out that the letdown from the non-strike at UPS could have lingering effects to organize Amazon.

The Teamsters have managed to get affiliation cards from a majority of drivers at the DGT5 facility in Atlanta, and in Chicago’s Skokie suburb, and several in Southern California, including workers at a mega-warehouse in San Bernardino (these were the sites for the strike). Like in New York, the road to finally getting recognition or contracts from Amazon still appears long. 

In these challenging times anyone, interested in the state of the American labor movement and especially its most iconic union, should make Teamsterland required reading. 

   

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