Mobbed-Up! The Untold Story of Sean O’Brien and Teamsters Local 25: A Rank-and-File Perspective

James Hoffa. left, and Sean O’Brien, center.

Editors’ note: This is the first of two articles with background about the union’s recent history, intended to inform readers about the election of officers now taking place in the Teamsters union (International Brotherhood of Teamsters).

The 2021 International Brotherhood Teamsters (IBT) General Election is under way and times for rank-and-file members could not be any bleaker. This year’s election will be a battle between two slates headed by current General Executive Board Vice-Presidents who ran on the 2016 Hoffa-Hall slate. One is Sean O’Brien, who heads the Teamsters United Slate of the troubled Local 25 in Boston with its historic ties to corruption and organized crime.

The other slate, Teamster Power, is headed by Steve Vairma of Local 455 in Denver. Neither O’Brien nor Vairma are reformers, nor do they have a plan for the future of the union or for leading a successful mobilization drive to unionize Amazon as discussed by reformers at the first post-debate debrief. More importantly neither plans to slash the multiple salaries and other excessive perks officers have enjoyed since James P. Hoffa’s win in 1998 restored the old-guard to power.

Vairma’s Teamster Power slate is made up of old-guard officers loyal to the current Hoffa administration in an attempt to keep the status-quo intact. For his part, O’Brien had a falling-out with Hoffa during the 2018 UPS contract negotiations. Rebuffed by Hoffa, in 2017 O’Brien reached out to the leaders and rank and filers of the Teamsters United movement. Hoffa then countered by firing O’Brien as director of the package division.

Following the 2016 Teamsters election it became quite evident that O’Brien, who had been Hoffa’s most ardent old-guard warrior in New England, had aspirations to seek the union’s top position in 2021. The UPS contract that represents over 250,000 members has been at the center of the fight in the Teamsters since 2013 when eighteen supplements were rejected by a membership enraged over healthcare changes that O’Brien himself had helped craft. In 2018 UPS workers rejected an agreement that created another tier of drivers, but using the two-thirds rule in the Teamster constitution (the need for a two-thirds majority to reject a contract) Hoffa imposed the contract, because less than fifty percent of the members voted.

Unfortunately for reformers, Fred Zuckerman, now the secretary-treasurer candidate on the Teamsters United slate, did not pick-up the fight for the members where he left-off in 2016. During the problematic 2018 UPS negotiations, Zuckerman secretly formed an alliance with O’Brien who used his ousting as UPS Package Director to disguise himself as a “reformer” and disregarded the hundreds of reform activists that had organized to reject eighteen UPS supplements in 2013. In fact, those who organized against the contract had become constant targets of intimidation and harassment from management and old-guard officers that included O’Brien. Some of these active rank-and-file reformers lost their jobs in the process as they campaigned relentlessly in the 2016 Teamsters presidential election to bring Zuckerman within less than 3.23 % of Hoffa’s vote. Still, reformers won six executive board positions. Nevertheless, in the current election cycle, Zuckerman agreed to give-up the Teamsters United top spot to a product of the most reactionary and thugged-up elements the Teamsters old-guard has to offer: O’Brien.

Not surprising, when O’Brien announced his candidacy for general president in May 2018 he had the arrogance and audacity to declare: “I told Fred we got to do it in Boston where great leaders like Dan Tobin and Bill McCarthy came from.” But what was the history and tradition of Boston Local 25?

The 1980s would become the most embarrassing and turbulent times for the Teamsters as President Ronald Reagan’s administration, after firing 11,345 striking air traffic controllers, waged open war against organized labor. At the same time Republican governors pushed anti-union right-to-work legislation in Republican ran states, while Democratic Senator Ted Kennedy pushed trucking deregulation through Congress, leading to the rise of non-union carriers in the freight industry. Within the union itself, Frank Fitzsimmons (1981), Roy Williams (1983) and Jackie Presser (1988) all finished their presidencies in legal trouble and as disgraced for their ties with both the Mafia and the FBI.

In 1988, the head of Boston Local 25 and New England’s Joint Council 10, William McCarthy succeeded to the general presidency in a nine-to-eight vote after a divisive political struggle within the mob-controlled Teamster General Executive Board (GEB). The civil Racketeer Influenced Corrupt Organization (RICO) Act suit had already been filed when he was sworn in. But more important to note is that McCarthy was not promoted to the highest office of the Teamsters based on his merits and working-class fighting credentials as O’Brien suggested. McCarthy was a loyal puppet of organized crime and he himself had allowed gangsters and thugs to infiltrate the ranks of his home local and Joint Council going back to the days he had gained control of their offices in 1955 and 1972.

In 1988 the U.S Department of Justice brought a 113-page RICO Act complaint, filed by the Southern District Court of New York (SDNY) that accused the Teamsters of being a subsidiary of organized crime. McCarthy was forced in March 1989 to agree to a consent decree that would rid the union of corruption and organized crime involvement. The consent decree also required several amendments to the IBT constitution that gave rank-and-file members the right-to-vote for the union’s GEB, ending the undemocratic and nepotistic structure of appointments. From 1988 when McCarthy was appointed General President, till the election of 1991, McCarthy looked incompetent, incapable and weak. The daily newspapers and television news stories about the Teamsters further tarnished the reputation of the Boston leader.

McCarthy had initially announced that he would seek reelection, but quickly was forced to abandon his candidacy when he failed to secure the support of the majority of the GEB. With the infiltration of the violent and criminal Winter Hill Gang into Local 25 and the constant headline stories about the troubled local on the front pages of The Boston Globe and The Boston Herald, in 1991, McCarthy lost his local election to George Cashman, an opportunist disguised as a reformer. This was followed by McCarthy’s resignation as Joint Council 10 president, a position he had held since 1972. So, he retired from the Teamsters in complete disgrace.

George Cashman (1992-2003): The Perfect Opportunist

Disguising himself as a reformer in 1991, George Cashman defeated McCarthy. At the time Cashman took over Local 25, it had become the constant subject of both local newspaper and television news stories due to its members notorious behavior and close association to the gangster James “Whitey” Bulger. Up and coming right-wing zealot Howie Carr, a columnist for The Boston Herald and host of a regional radio show has since the 1990s made a name for himself exposing the corrupt legacy of Local 25, Whitey Bulger and the Winter Hill Gang. The same thuggish characters that roamed Local 25 during McCarthy’s reign continued to so under Cashman.

In 1994 The Boston Herald reported that an ex-con turned movie crew chief of Local 25 – William “Billy” O’Brien, was named in an indictment for an armored car robbery in New Hampshire that ended in the execution of two guards. William O’Brien who is the father of Sean O’Brien was never charged for renting the getaway truck used in the heist.^[1] Interestingly following the armored car heist, in an interview with AMA Highlights magazine, Carr shared that the FBI raided the home of the elder O’Brien and found $50,000.^[2] According to sources, at least seven of the eight men cited by investigators in the 1994 robbery and executions of the two armored car guards in New Hampshire have worked for Local 25’s movie division.^[3] Over the years there has been speculation in the media and by some Teamsters that O’Brien cooperated with federal investigators following the heist and so was not charged.

In April 2003, Cashman, pleaded guilty to conspiracy charges. He admitted falsifying timesheets to allow nine-teen truck drivers to illegally collect more than $72,000 in health benefits. One of the drivers was John “Mick” Murray, an admitted associate of by then fugitive gangster Whitey Bulger.^[4] In a separate scheme, The Middletown Press added that Cashman admitted to extorting $100,000 from a health care company, and pocketing $20,000 of the money. Because of his conviction, Cashman lost his two positions at Local 25 and Joint Council 10 and was barred from being employed by the union for thirteen years. Cashman was sentenced to serve over thirty-four months in prison for his scheme as head of Local 25.^[5],

Sean O’Brien (2006-): The Lust for Power

When Sean O’Brien took over as head of Local 25 in 2007, he did so with the opportunity to clean-up the local’s corrupt and notorious past. O’Brien could have purged the criminal elements that had infiltrated his local going back to the McCarthy days. But like Cashman before him, he allowed them to remain in his local and roam with the same free pass his predecessors had provided them. In fact, some of these thugs have since 2007 become O’Brien’s personal goons and are best referred today as “Seanies.” But O’Brien didn’t lift a finger when it came to addressing the ills that have afflicted Local 25.

O’Brien is a man who will stop at nothing to achieve his ends. In the past he has been referred to as the “the Boston Bully” for his behavior against reformers and those challenging his closest allies. His past attacks on reformers and his spectacles at multiple IBT Conventions demonstrate that he is a bully. In 2013 O’Brien was suspended for threatening members and in 2016 was caught lying to the Office of the Election Supervisor for the IBT. Lacking any principles or integrity other than self-advancement, O’Brien has zig-zagged and flip-flopped his way through Teamster politics since 2017—the year Hoffa fired him as UPS Package Director.

Despite O’Brien’s faults there is no denying he has a cult-like following among his supporters in New England. He was elected as the youngest GEB member on the Hoffa-Hall 2011 ticket and the highest vote getter as candidate for Eastern Region Vice-President. In the past, O’Brien has shown off his support with the entourage of goons that has accompanied his delegations to the IBT conventions in Las Vegas every five years and yearly “unity” conferences. O’Brien, who climbed the bureaucratic ladder of the IBT through nepotism, is a political chameleon that has managed to change his position and behavior to benefit his career and goal of becoming Teamster president. Together with Hoffa and Rome Aloise of Oakland, he is the most dangerous Teamster bureaucrat remaining in the union holding a position of power.

O’Brien missed his opportunity to shine as a great Teamster leader during the 2013 UPS Contract negotiations when he was appointed coordinator of supplemental contract negotiations. Instead, O’Brien worked in collusion with UPS management to harass Vote No activists and because of him, some were fired. At Local 804, the home of Ron Carey and leader of the 1997 UPS Strike—O’Brien attempted to strongarm Teamster members into accepting a concessionary supplement. Former leader of Local 804 Tim Sylvester best summed it up in 2017 following O’Brien’s removal as UPS Package Director:

Where was Sean O’Brien’s tough talk about Hoffa before he got fired? Sean O’Brien backed Hoffa without a word of criticism in the last election. In fact, he threatened any member who dared criticized Hoffa. During the last contract negotiations, O’Brien tried to strong-arm my local into accepting a lower pension increase and eliminating twenty-five and out. We refused and united the members instead. We won a $400/month pension increase including twenty-five years of service and out regardless of age. Now after his termination by Hoffa, Sean says he is for the members and this is not about politics.

Pension Fund Problems

In fact, in 2005 O’Brien’s New England Teamsters Pension Fund was forced to eliminate their twenty-five and out program do to pension inefficiency and was forced to raise retirement eligibility to age 57.^[6] No other Teamsters pension fund requires any members to work to late an age. Since O’Brien took over as head of Local 25, the New England Pension Fund has continued to suffer from financial mismanagement and failure to make adjustments. In December 2008, the fund was certified by its actuaries to be in “critical status” as defined by the Pension Protection Act (PPA).^[7]

Although O’Brien was not a union Co-Chairman of the fund in 2008, he served as one of three trustees when it entered “critical status.” Since taking over as co-chairman the fund has not stopped declining. The fund entered “critical and declining’ status in 2012 when it fell below the 65% funding level—triggering a decision by UPS to pull-out from contributing into the failing fund.^[8] Under O’Brien’s watch the past five years have been the worst for the New England fund since it was founded in 1958. The collapsing fund began the 2020 year at 48.2% funded, the second worst after the Central States Pension Fund and it will require a government bail-out provided by funds from the Butch Lewis Act passed by Congress last April.

The rapid collapse has to do with the New England Pension Fund currently having more retirees collecting benefits than members contributing to it. The problem lies in the region’s failure to organize new members. As leader of New England’s Joint Council 10, O’Brien has been unsuccessful in leading any significant union organizing drives that would have brought new contributing members into the union and helped the struggling fund, this despite New England states having amongst the friendliest labor laws in the nation and not having any right-to-work states. There is no one else to blame for this failure but O’Brien himself who is the sole decision maker regarding organizing drives by Joint Council 10.

Also, under O’Brien Local 25 has continued to be the subject of not only local media stories, but national ones as well thanks to its continuing violent behavior. He himself was suspended for 10 days for threatening the members of Local 251 in a sister local in Rhode Island. O’Brien’s failure to change the local’s horrible reputation is an embarrassment to every hard-working rank-and-file member and a blemish that has not yet disappeared despite the federal government’s takeover of the union.

This analysis is not an endorsement of any slate. This article is intended to expose Sean O’Brien and to reveal Boston Teamsters Local 25 for the failure it has been. As the ballots make it to members’ homes this October, it is very important that each and every one of those members knows this history before they vote. O’Brien is nothing more than an impostor disguising himself as a reformer.

It should be the duty of all rank-and-file members to study the lessons of the past as a necessary precondition to better their union at a time when greedy corporations have waged open war against them. In the words of the great Spanish-American philosopher George Santayana: “He who does not learn from history will forever be doomed to repeat it.”

Edgar Esquivel has been a member of Local 952 UPS Teamsters in Orange County CA for over twenty years. He was formerly an activist with Teamsters for a Democratic Union (TDU). He holds a Master’s Degree in History from California State University-Fullerton and has served as an adjunct professor of History at both Mt. San Antonio College and Santa Ana College in Southern California. He has in the past written for Socialist Worker.

[1] “Winter Hill Gang Nets True Crime Figures,” IGN Entertainment, June 17, 2012. https://www.ign.com/articles/2001/11/20/winter-hill-gang-nets-true-crime-figures

[2] “Howie Carr,” AMA Highlights. https://amahighlights.com/howie-carr/

[3] Jack Sullivan, “Teamsters movie crew includes some very bad actors,” The Boston Herald, July 27, 2000.         CNN – Local News – Teamsters movie crew includes some bad actors – July 27, 2000

[4] Denise Lavoie, “Teamsters Leaders Plead Guilty to Fraud,” The Middletown Press, April 26, 2003.

Teamsters leaders plead guilty to fraud (middletownpress.com)

[5] Editorial, “Teamsters case shows: Goons are bad for business,” The Boston Globe, September 26, 2012.

Teamsters case shows: Goons are bad for business – The Boston Globe

[6] “Pension Cuts Hit New England,” Teamsters for a Democratic Union, July 27, 2005. Pension Cuts Hit New England (tdu.org)

[7] 2009RehabPlan.pdf (nettipf.com), 1.

[8] Barry B. Burr, “UPS to leave New England fund, strikes new funding deal,” Pensions & Investments, August 27, 2012. UPS to leave New England fund, strikes new funding deal | Pensions & Investments (pionline.com)