The Teamsters for a Democratic Union (TDU) held its 44th annual convention in Chicago in early November, where it endorsed Sean O’Brien for General President and Fred Zuckerman for General Secretary-Treasurer in the 2021 Teamster election. They will run on the “Teamsters United” slate and challenge the incumbent leadership, whether it is led by the incumbent General President James P. Hoffa, Jr. or an anointed successor.

TDU’s endorsement is crucial for any candidate seeking to run as a reformer against the Teamster establishment — notorious for its bloated and corrupt officialdom and ties to organized crime. TDU has been the leading voice for reform in the Teamsters for four decades and played a major role in Zuckerman’s 2016 election challenge, when he came within a few thousands votes of toppling Hoffa from power. Now, it’s O’Brien’s turn to lead the slate.

But TDU’s endorsement of Sean O’Brien didn’t pass without controversy. O’Brien was a notorious Hoffa supporter — before he was fired by Hoffa — and has a well-deserved reputation for thuggery. Some current and former TDU supporters took to social media to criticize the endorsement, while raising serious concerns about the future of the reform movement.

Since the TDU convention, unease about O’Brien increased after he called off his local’s eighty-four day strike against Republic Services, the second-largest waste management company in the country. The strike ended in a complete defeat, raising questions about O’Brien’s leadership. As we enter the twilight years of the Hoffa era, where are the Teamsters going?

Hoffa in Twilight

Rumors of Hoffa’s impending retirement have been circulating for some time now. He was expected to announce his retirement at the October General Executive Board (GEB) meeting at the union’s headquarters in Washington, D.C. and dictate a successor. With a comfortable majority on the board, an easy transition was planned. But the meeting came and went with no announcement.

Speculation then turned to why it was taking so long. Hoffa is seventy-eight years old after all, and recent subpar performances at national Teamster conferences has led to a lot of gossip that he’s not up for the job any longer. The last national contract that he had a hand in — the 2018 national UPS contract — was voted down by the membership but “ratified” by him in a highly unpopular maneuver. Picking a successor may be more difficult than Hoffa expected.

Rumored successors such as Terry Hancock of Chicago or Kevin Moore of Detroit have serious baggage. Hancock, the president of Chicago Teamster Local 731, is embroiled in a hostile and unpopular takeover of another local union. Moore, the president of Detroit Local 299, the home local union of the Hoffa family, has proved to be an unpopular carhaul director.

Hoffa’s delayed retirement may have to do with him positioning the union to play an important role in the 2020 Democratic presidential primaries. For example, on December 7, the Teamsters cosponsored a Democratic presidential forum on workers rights in Cedar Rapids, Iowa, two months before the Iowa caucuses. Joe Biden and Bernie Sanders were the candidates who attended.

Despite having endorsed Hilary Clinton in 2016, this is something of a political pivot for Hoffa who earned a reputation as one of President Donald Trump’s most reliable union supporters on trade and infrastructure projects, including the environmentally disastrous Keystone XL and Dakota Access Pipelines and the ongoing trade war with China. Lately, however, Hoffa has soured on Trump. He told the Huffington Post in late October:

He [Trump] made promises about how he would be [a workers’] champion. I think he can do better than what he’s done. I think he could have done more to help us with collective bargaining, more to help us with pensions…. I think he could have done more for us. I do.

Hoffa admitted in an October interview that many Teamsters voted for Trump in 2016. Hoffa also predicted that many “Teamsters are likely to vote for Trump again in 2020, regardless of who the Democratic nominee turns out to be.” Such honesty may be refreshing from the likes of Hoffa. He may have astutely judged that there is a battle on the horizon for Teamster votes, especially in Michigan, the home state of the Hoffa family with a large active and retired Teamster voting bloc. In an April 3, 2019, Detroit News column titled “Michigan Will Play Critical Role in 2020 Election,” Hoffa wrote:

Michigan finds itself at the forefront of the 2020 presidential election conversation. Thanks to the slim victory voters gave to President Trump here in 2016, those running for president this time know they need to win the Great Lakes State if they want to reach the White House.

Some Teamster votes were responsible for Trump winning in Michigan — and other states in the upper Midwest — which allowed him to eke out a victory in the Electoral College, bringing catastrophe to us all.

A Fraying Old Guard

Hoffa’s old guard has been fraying for the past two Teamster elections, with previous supporters — many of whom were pillars of his coalition — running against him. In 2011, Hoffa was challenged by longtime supporter and Wisconsin Teamster leader Fred Gegare, who told the Milwaukee Journal Sentinel that he decided to run because “James Hoffa Jr. is dismantling the union his father built, piece by piece.”

Gegare’s sudden conversion from hack to opposition candidate was greeted with mockery from TDU. In an informational bulletin about Gegare’s candidacy titled “Why He Can’t Win…and Why That’s a Good Thing,” TDU asked, “Why is Gegare running against Hoffa?”:

That’s a good question. Gegare is long-time Hoffa loyalist. As a candidate, he criticizes Hoffa’s handling of the Central States Pension Fund and Hoffa’s concessions to UPS and UPS Freight. But Fred’s rhetoric doesn’t jibe with his record.

Despite the weak basis of Gegare’s campaign, Hoffa’s aides and campaign staff were unnerved by the revolt of loyalists, including Fred Zuckerman, President of Local 89 in Louisville, Kentucky, who also ran on Gegare’s slate. Hoffa’s inner circle was so desperate that they offered a bribe to Zuckerman. “They expected me to support the Hoffa slate and not run against him,” Zuckerman reported to the Teamster election supervisor Richard Mark.

In the end, Hoffa handily won reelection with 137,000 votes against Gegare and TDU leader Sandy Pope. Gegare won a little over 54,000 votes, while Pope also did surprisingly well: supported by a small number of dedicated volunteers but little money, she received nearly 40,000 votes. Pope was also the first woman to run for the top spot, a milestone in the U.S. labor movement.

“Teamsters United” was born out of the veterans of Gegare’s old slate and TDU supporters and members. For the 2016 Teamster election, Teamsters United first nominated Tim Sylvester, the President of Local 804 in New York City, to be candidate for General President. Sylvester, a former UPS driver, was a veteran Carey supporter and activist.

Sylvester won the race for the leadership of Local 804 in 2009 on the 804 Members United slate, beating the incumbent two to one. The local was the longtime political home of Ron Carey, the first and only reform leader of the Teamsters. Under Sylvester’s leadership, the local made important gains in contract negotiations against UPS, by far the biggest employer for Local 804 members.

While Teamsters United got off to a strong start, it was badly jolted when Sylvester narrowly lost reelection for local office after a highly factionalized and destructive campaign in 2015. As a result, Sylvester switched positions on the slate to run for General Secretary-Treasurer. Fred Zuckerman stepped forward to run for General president. He was Hoffa’s carhaul director before being fired by him. Despite this blow to the campaign, Zuckerman rose to the occasion. He was a down-to-earth person with a straight-talking style, which had a great appeal to Teamsters used to bluff and bluster.

Zuckerman made a name for himself on the campaign trail for his aggressive attacks on Hoffa’s unnecessary concessions to UPS in 2013, the lack of organizing in freight and carhaul, and — most importantly in the Midwest and South — the looming bankruptcy of the Central States Pension Fund on Hoffa’s watch. Sean O’Brien came in for a special skewering because he the coordinator of the UPS contract supplement that were repeatedly voted down but ultimately imposed by Hoffa.

When the ballots were counted Hoffa nearly lost the election, and his regional vice presidents were wiped out in the Midwest and the South, replaced by virtual unknowns from the Teamsters United slate. Chicago-area Teamsters voted for Zuckerman and Teamsters United by a slim margin, something inconceivable in previous elections. A large minority of Teamsters were prepared to vote for any credible alternative to Hoffa.

Yet apathy and cynicism was also hallmark of the 2016 election, which had the lowest turnout since the first rank and file election in 1991. It should be noted that during this time, Sean O’Brien was a menacing Hoffa loyalist.

“Old-School Values”

It’s been an open secret for many years that Sean O’Brien wants to be General President of the Teamsters. He was thirty-four years old when he was elected president of Teamsters Local 25 in Boston in 2006, making him the youngest person elected to that position in the local’s history. Local 25 has over 12,000 members in a variety of industries, but the largest employer by far is UPS, the logistics giant.

Teamsters Local 25 has never had a good reputation. Boston Magazinesummed up its sordid history pretty well a few years ago:

The union had ties to Whitey Bulger’s Winter Hill Gang; one of its former presidents spent time behind bars; its rank-and-file members have been convicted of crimes ranging from armed truck robbery to embezzlement; its officers once had a reputation for shaking down movie crews. In 2011, a retired union member was found dying on a train platform carrying $180,000 in mysterious cash.

Local 25’s long time president was William J. “Billy” McCarthy, sometimes called “mad dog.” He ruled the local from 1955 to 1992. McCarthy was a longtime associate of organized crime. McCarthy’s successor was George Cashman, who styled himself a “New Teamster” and allied himself with Ron Carey, but he let the gangsters run amuck in the local’s movie division. According to Boston Magazine writer Michael Damiano:

Local 25’s movie crew, where Sean O’Brien worked and his father was a transportation coordinator, was earning a reputation for extorting Hollywood filmmakers. In 1994, a top representative of Local 25’s movie crew was convicted on federal conspiracy charges connected to a mob-related scheme to extract bribes from movie executives.

In 2003, George Cashman pled guilty to two counts of conspiracy in relation to embezzlement and extortion schemes and was sentenced to federal prison. O’Brien ran for local office in 2006 on what Damiano called a “conservative pitch.” “We needed to go back to our old-school values,” O’Brien exclaimed. “Go back to what made us successful.” “Old-school values” is a loaded phrase in Teamster politics, harkening back to the days of mob control and violence with a heavy dose of nostalgia for a “strong leader.”

O’Brien quickly allied himself with Hoffa on the national level and was rewarded by being added to Hoffa’s slate. He was elected an international vice-president for the eastern region in 2011. Hoffa rewarded O’Brien again by naming him the coordinator for the supplements and riders to 2013 national UPS contract. While the 2013 national contract passed by a slim majority, the supplements were repeatedly voted down because of membership anger at unnecessary concessions.

“O’Brien coordinated supplemental contract negotiations in 2013,” according to the Teamsters United website, “when a record 18 regional and local supplements and riders were rejected by the members.” Hoffa, prefiguring his actions in 2018, nevertheless imposed the national contract and supplements on an angry membership in 2014. O’Brien said and did nothing to oppose this.

In 2013, Rhode Island Teamsters got a taste of O’Brien’s “old-school values” when he directly intervened in the election of Local 251. Faced with a strong challenge from the TDU-aligned slate of reformers led by UPS driver Matt Taibi, the old guard incumbent Joe Bairos called in O’Brien for help. At a fundraising rally, O’Brien threatened retaliation against anyone who voted for Taibi and his United Action slate:

“I’ve got news for you, anyone who takes on my friend, Joe Bairos and his team, or Local 251, they’ve got major problems,’’ O’Brien said, according to transcripts of the union hall rally in Rhode Island during late summer. “They’ll never be our friends. They need to be punished. They need to be punished, and they need to be held accountable for their actions, trying to divide and tear down this local.’”

O’Brien was charged with intimidating members and suspended for fourteen days by the Independent Review Board, a disciplinary body created by the federal consent decree in 1989 that guaranteed rank-and-file elections free from the threat of violence and intimidation.

But by far the most notorious episode of O’Brien’s reign was the Top Cheffiasco. The popular cooking series on Bravo is hosted by former model Padma Lakshmi. On June 10, 2014, Top Chef was started filming at the Steel & Rye restaurant in Milton, a suburb of Boston, without union labor. A Local 25 picket line was set up and led by Secretary-Treasurer Mark Harrington.

Instead of focusing on the use of nonunion labor, an explosion of racist, sexist, and Islamophobic slurs took place, including the threat, “That’s the pretty one. We want to smash her face in.” The activities of O’Brien’s crew were almost entirely recorded by cell phone. Federal prosecutors in Boston, who have a long antiunion record, quickly jumped on the case and indicted five Local 25 member including Mark Harrington for extortion under the Hobbes Act.

Harrington was so certain he would be convicted that he pled guilty, while four others went to trial. Luckily for the labor movement, the jury returned a not-guilty verdict. A conviction would have had serious repercussions for the rights of workers to picket employers across the country. The jury’s decision doesn’t, however, absolve the racism and bigotry displayed by O’Brien’s men. Charges of racism were at first dismissed by O’Brien as “fiction at best,” but he was forced to eat his words after the recording of his men surfaced.

O’Brien once again displayed his “old-school values” by verbally assaulting reform delegates at the Teamsters convention in June 2016 in Las Vegas. His behavior and that of other Hoffa delegates was investigated by the Office of the Election Supervisor of the Teamsters, and while it wasn’t deemed to have risen to the level of preventing nominations, one investigator reported that O’Brien “lied” to them. O’Brien went on to deliver a solid block vote from his local union that endorsed Hoffa’s reelection.

For his loyalty, Hoffa appointed O’Brien director of the Teamsters Package Division in February 2017, setting him up to be the chief negotiator for the 2018 contract. “With Sean’s experience, enthusiasm and commitment I am confident that he will lead the fight for our members to achieve a strong contract,” said Hoffa

Fred Zuckerman was not so pleased, “UPS Teamsters voted for new leadership to fight for a strong contract,” he said. “Instead, Hoffa is serving up a retread who screwed up the last negotiations and imposed weak contracts and concessions.” O’Brien’s subsequent falling-out with Hoffa blocked his rise to Teamster General President, and so he has sought another route. Given O’Brien’s clear record, it is a serious mistake for TDU to endorse him for General President and bestow on him the image of a reformer.

Where Are the Teamsters Going?

James P. Hoffa Jr. has been leader of the union for twenty years. He’s won five successive elections. Despite his winning streak, Hoffa has never been a particularly popular leader. If he retires as expected, it very probable that the old-guard coalition he relied on as his power base will crack up into competing factions, possibly reflecting regional rivalries.

As past Teamster elections have shown, if the old guard is split in two or three parts, reformers have their best chance of winning; that’s what happened in the first rank-and-file election that brought Ron Carey to power in 1991. Still, with nearly two years to go before the election, it’s anyone’s guess how many candidates and slates will be campaigning for the top spots in the union and whether a reform slate stands a good chance.

All of the announced or probable candidates for General President — by far, the most powerful position in the Teamsters — carry huge political baggage with them or have potential skeletons in their closets, so it’s hard to know how many of them will make it to the finish line. For example, another ambitious Teamster leader, Rome Aloise, the Secretary-Treasurer of Local 853, whose two-year suspension from the union ends later this year, plans to run for General President. How can he possibly think he can be a candidate without being subjected to greater scrutiny?

The issues the next Teamster leadership will face — the continued rise of nonunion giant Amazon, the prospects of the next recession savaging the traditional freight industry, self-driving trucks, surveillance in the workplace, the dire issues of environmental destruction and the union’s posture towards a Green New Deal — aren’t going away. None of the announced or probable candidates running for Teamster General President are up to the task of confronting them. The Teamsters are long overdue for a fundamental change in direction after two decades of stagnation.