Teamsters Local 299

Teamsters Local 299 was the Detroit union local that brought Jimmy Hoffa into professional organizing after his 1932 victory with the Strawberry Boys. It became his home local, a source of authority and political support, and later the ground on which he planned to reclaim leadership of the International Brotherhood of Teamsters. Through the local, the book traces how organizing work, pension resources, personal loyalty, and formal succession rules could converge in one institution—and how that institution remained contested even while Hoffa was imprisoned and later restricted from managing a union.

From the Strawberry Boys to Detroit Organizing

In 1932, nineteen-year-old Jimmy Hoffa worked as a loader and unloader of fresh produce at the Kroger Food Company in Detroit. The job paid 32 cents an hour, with 20 cents issued as credit for groceries, and workers were paid only when there was work. They reported at 4:30 in the afternoon for shifts that could last twelve hours, with no permission to leave the platform. When a hot afternoon brought a load of strawberries from Florida, Hoffa signaled the workers to stop moving the fruit into refrigerator cars until the company recognized their union and addressed their demands.

The workers, later known as the Strawberry Boys, sought a guarantee of four hours’ pay for each twelve-hour shift. With the strawberries at risk in the heat, Kroger gave way and granted the new one-company union a one-year charter. The following year, the company refused to negotiate another contract, and the victory proved temporary. But the campaign had made Hoffa visible: Teamsters Local 299 recruited him as an organizer, charged with persuading workers to join and using collective organization to improve their lives and their families’ prospects.

That recruitment placed Hoffa in the midst of Detroit’s industrial labor conflict. The book describes employers hiring strikebreakers and private muscle to weaken picket lines, while scarce jobs made it difficult for workers to sustain a strike. Against this backdrop, Local 299 was not simply the next rung in Hoffa’s career. It was the organization through which the young organizer could turn the Strawberry Boys’ brief success into an enduring role in the union movement.

Hoffa’s Home Local and Sheeran’s Apprenticeship

By the time Frank Sheeran arrived in Detroit, Local 299 was Hoffa’s home local, located on Trumbull Avenue down the street from Tiger Stadium. Its organizing campaign among Detroit cab drivers gave Sheeran a practical introduction to union work. He joined about eight organizers who assembled each morning, then went to garages and cab stands to picket and distribute flyers prepared by Bill Isabel and Sam Portwine. The campaign took them to places including Cobo Hall and the Warner Hotel, where organizers approached drivers, explained the benefits of union membership, and asked them to sign union cards.

Sheeran learned that an election could be triggered once organizers had signatures from 30 percent of the workers, but that Isabel advised waiting until support exceeded 50 percent. A rival union could intervene with signatures from 10 percent, potentially defeating the organizing effort after Local 299’s team had done the initial work. The practical lesson was that an organizing drive depended on building a margin of support, not merely meeting the threshold for an election. Local 299’s campaign thus brought Sheeran into the everyday work of persuasion, picketing, and competition between unions.

Sheeran hoped to become an International organizer, a post that would take him around the country and allow him to help people through legitimate union work. He believed that, if he succeeded in Detroit, he might later return to Philadelphia as an organizer attached to Teamsters Local 107. Local 299 provided the training ground and the connection to Hoffa that made that ambition possible. Sheeran recalled being pleased to work where Hoffa worked, and his meeting with Hoffa in Chicago strengthened the sense that he had entered the right institution and found a powerful sponsor.

The local’s influence was also visible in the personal network around Hoffa. At a dinner in Chicago, Hoffa asked Sheeran about his daughters and spoke about the Teamsters’ expulsion from the AFL-CIO and the pressure surrounding the union. The dinner connected the local organizer to the national leadership, while the work in Detroit tested whether he could perform the role. Bill Isabel and Sam Portwine recommended that Hoffa keep Sheeran with them so he could learn more. Local 299 therefore functioned both as a workplace and as a path into a larger union hierarchy.

Pension Power and Institutional Risk

Hoffa’s work in the Teamsters extended beyond organizing campaigns. In 1955 he established a pension fund into which employers made regular contributions for truckers’ retirement; previously, many workers had little to rely on beyond Social Security. The book describes Hoffa pressing trucking companies to create the fund on terms that gave him influence over its administration and over which borrowers could receive loans. As contributions accumulated before covered workers began retiring, the fund grew from roughly $200 million by the time Sheeran came into the union to a billion dollars by the time he retired.

That pension system carried consequences for workers and for the union’s political economy. The fund provided a new retirement resource, but its loans also became a source of financing for ventures connected to organized crime. The account describes Hoffa approving loans for selected associates and taking an off-the-books finder’s fee when customers were brought to the fund. These broader arrangements should not be confused with Local 299’s organizing work, but the local’s Detroit pension money became directly relevant in the Sun Valley Village case.

Before the Sun Valley development went bankrupt in 1958, Hoffa authorized $400,000 from the pension fund of his Detroit local to be placed in a Florida bank account as collateral for a developer’s loan. The money was intended to secure financing for roads and utilities. When the project failed, the bank retained the collateral, and recovering the $400,000 required paying the bank a total of $500,000 owed by the developer. The government alleged that Hoffa and seven codefendants then made a series of loans from 1958 to 1960, charging points and finder’s fees and directing some of the proceeds toward repayment. Hoffa ultimately repaid the $400,000 to the local’s pension fund and paid $42,000 in lost interest. Prosecutors argued that his personal interest in the development and the loans made the transactions fraudulent; they pointed to a secret trust agreement under which he was allegedly to receive 22 percent of the development’s profits.

At the 1966 Miami Beach convention, Hoffa changed the union constitution to create a general vice-president position with authority to run the union if the president went to prison. He installed Frank Fitzsimmons in the new role, while raising his own annual salary from $75,000 to $100,000 and securing its continuation if he were incarcerated. Delegates also approved payment of his past and future legal expenses; the past expenses totaled $1,277,680 at the time. These were decisions about the International Brotherhood of Teamsters, not Local 299 alone, but they shaped the local’s future: Hoffa’s capacity to return to power depended on a union structure in which his supporters and successor could preserve his influence.

Sheeran’s Local 299 Presidency and the Local Network

After Hoffa divided Teamsters Local 107 into three locals, he gave Sheeran the charter for a new Wilmington local, Teamsters Local 326. Sheeran became its acting president pending an election. Hoffa’s first instruction was that he go to Philadelphia and dismiss five disruptive organizers whom the Teamsters Local 107 president, Mike Hession, was unwilling to fire. Sheeran dismissed Johnny Sullivan, Stevie Bouras, and others, including Big Bobby Marino and Benny Bedachio. He stayed in Philadelphia for a time to watch for retaliation, then returned to Delaware and learned the work of his new position firsthand, spending two weeks driving a car hauler at a Chrysler plant because he did not want members to doubt his understanding of their grievances.

Sheeran later described his presidency of Teamsters Local 326 as his favorite part of his working life. The local had previously been run from Philadelphia; Hoffa’s charter gave it its own standing. Sheeran said he handled members’ grievances and enforcement of their contracts day to day. When he was incarcerated, the local made him Honorary President for Life. He recalled that it had more than 3,000 members when he went to jail and about 1,000 at the time of his account. In 1979, he obtained a new building for its headquarters, replacing the earlier office at 109 East Front Street in a rundown neighborhood by the railroad station.

This account of Sheeran’s local presidency clarifies why Detroit’s Teamsters Local 299 mattered beyond its own membership. Hoffa’s support and charters could shape the organization of other locals, while the local presidents who emerged from that network could carry his influence into union politics. Sheeran’s loyalty to Hoffa was personal, but it was also expressed through institutional acts: accepting assignments, organizing members, handling grievances, and building an independent local.

Succession, Restrictions, and the Fight over Detroit

Hoffa’s imprisonment did not end his claim on the union. He hoped to return to the presidency, and the July 1971 convention offered a possible route if he were released in time. Fitzsimmons had said he would run for president if Hoffa did not make parole, a challenge made more consequential by the fact that Hoffa still held union offices while incarcerated. Hoffa’s release came on December 23, 1971, after President Nixon commuted his sentence, but the commutation barred him from direct or indirect management of any labor organization until March 6, 1980. The condition left him free but unable to take the union role he had been working to recover.

The restriction redirected the contest toward Local 299. Dave Johnson, Hoffa’s old associate, remained its president. The plan was for Johnson to stay in office until Hoffa could return to the International; once the restriction ended, Johnson would appoint him as a business agent, making him a delegate eligible to challenge Fitzsimmons at the 1976 convention. Fitzsimmons, meanwhile, pressed Johnson to retire early so that he could appoint his own son, Richard, to lead the local. The struggle over Detroit was therefore a struggle over a specific institutional pathway: control of Local 299 could determine whether Hoffa had a route back to national leadership.

The pressure on Johnson escalated. He received hang-up calls at home, and someone fired a shotgun at the window of his office in the union hall. About a week before Hoffa lost the first round in court over the restriction, someone blew up Johnson’s forty-five-foot cabin cruiser. The book presents these attacks as messages from Fitzsimmons and his allies, while reporting that Fitzsimmons’s son accused Hoffa of being responsible for the boat explosion. Johnson remained president; he and Richard Fitzsimmons reached an arrangement under which Richard became vice-president instead. Later, Richard’s car was also blown up. The sequence left the local’s leadership in place but made clear how precarious that position had become.

Hoffa’s connection to Local 299 remained visible in the final period before his disappearance. In May 1975, he testified before a grand jury investigating no-show jobs at his former Detroit local and invoked the Fifth Amendment. Afterward, he told a reporter he was proud of doing so. That same day, he met with his son and Anthony Giacalone, who tried to arrange a meeting with Tony Provenzano; Hoffa refused. In late May, Fitzsimmons threatened to place Teamsters Local 326, Sheeran’s former local and another of Hoffa’s power bases, under trusteeship. Local 299 and Local 326 were distinct institutions, but together they reveal the reach—and vulnerability—of the network Hoffa had built through local union leadership.

Local 299’s significance lies in that long passage from shop-floor organizing to contested institutional power. It began in the story as the union that recognized Hoffa’s organizing ability after the Strawberry Boys’ brief victory. It became the Detroit base from which he built his career, the source of pension funds implicated in a major fraud prosecution, and the prize at the center of a succession struggle conducted through appointments, constitutional rules, court challenges, and intimidation. Its importance did not disappear when Hoffa went to prison or when his freedom came with a union-management ban; instead, control of the local became one of the ways his return could still be imagined—and opposed.