IUOE president James T. Callahan, who himself takes home nearly half a million dollars a year in union compensation, employs family member Thomas Callahan as the vice president of the union on a salary of $113,000 per year. James J. Callahan, meanwhile, makes about $250,000 annually as a director, and John Callahan receives roughly $215,000 per year for his work as an equipment assistant.

Tax forms only identify the three as “family member[s]” of Callahan, not divulging their specific relationships. He does, however, have a son named James, according to a union biography.

In addition to Callahan paying his family members handsome salaries, he’s also directed the union to spend millions of dollars on stays at luxury hotels and resorts. In late 2022, for instance, the union spent over $700,000 on lodging and meeting expenses at the Swan and Dolphin at Walt Disney World. The Disney-affiliated hotel is “centrally located in the heart of the Walt Disney World Resort,” according to its website. 

The union has spent millions more on stays at beach-front resorts, including multiple trips to locations in Hawaii. The biggest such expense was nearly $2.9 million paid to the Diplomat Beach Resort in Hollywood, Florida, for lodging and meeting costs related to the union’s 2023 convention. Among other amenities, the Diplomat Beach Resort features a 1,000-foot-long semi-private beach, poolside bottle service, an award-winning on-site steakhouse, and complimentary watersports rentals.

“When union officials object to proposed reforms to increase democratic control over whether workplaces should remain unionized — things like right-to-work laws, recertification requirements, and the like — they often claim that unions are democratically administered through internal elections,” Mike Watson, research director at the Capital Research Center and an expert on organized labor, told the Washington Examiner. “While technically true, the extent of nepotism in union officerships like that demonstrated by the IUOE is evidence that such democratic control by the membership is often more theoretical than actual.”

Callahan’s spending on salaries paid out to his family members and on events held at upscale hotels is funded by dues collected from rank-and-file members of the IUOE. The IUOE primarily represents heavy equipment operators working in the construction industry, mechanics, building maintenance workers, and land surveyors. The union also counts a smaller number of healthcare and petrochemical workers among its members. 

Future Forward PAC, the largest super PAC supporting the Democratic bid for the White House, was among the biggest beneficiaries of the IUOE’s political spending, taking in over $2.2 million in contributions. Senate Majority PAC, the primary political committee tasked with electing Democrats to the upper chamber, meanwhile, received more than $6 million from the union. Other major recipients of political funds from the union included the Harris Victory Fund, the DCCC, the Democratic National Committee, the event fund for the Democratic National Convention, and various state-level Democratic parties. The union did make a handful of much smaller donations to Republicans. Rep. Nick LaLota (R-NY), for instance, received tens of thousands of dollars in donations from both the national IUOE and some of its local branches. 

The IUOE has historically been criticized for nepotism, corruption, and even proximity to organized crime. In 2013, IUOE members accused the union of illegally spending union dues, squandering union funds via nepotism, collaborating with global organized crime networks, and threatening members of the union if they didn’t comply with its wishes. IUOE officials have been convicted of embezzlement, conspiring to commit extortion, and helping to conceal felonious activities. Additionally, a local branch of the union admitted in a plea deal that for some time, the construction industry in New York City has been infiltrated, controlled, influenced, and corrupted by La Cosa Nostra families.” 

La Cosa Nostra is a name used to refer to a collection of Italian-American crime families that have operated in the United States since the 1920s. The IUOE has faced multiple investigations, with some leading to convictions, over its dealings with the mob.

“This is not even a trend, it’s an ongoing scandal,” National Right to Work President Mark Mix told the Washington Examiner. “There are reports going back to the early days of labor unions about this type of nepotism.”

Mix went on to cite several examples of labor union leadership prioritizing family members for well-paying officer roles. An International Brotherhood of Boilermakers union chief, for instance, accused former union president Newton B. Jones in a federal plea agreement of misappropriating millions of dollars in union funds to keep his family members on payroll and to cover personal expenses, such as trips to Europe with his wife who happens to be 40 years younger than him. Mix also pointed to International Longshoremen’s Association president Harold Daggett. Daggett paid himself a salary of $855,261 in 2023 and his son, Dennis, received $467,664 from a high-level job in the union that same year. The ILA, like the IUOE, has spent millions on jaunts to upscale resorts and hotels for union leadership. 

“As these generational ‘leadership’ clans and cliques progress, you find that many of these executives and officers have never even been on a job site — that’s one of the things that happens with nepotism,” Mix continued. “The disconnect is growing wider and wider … not only just representing and understanding what the rank-and-file workers are dealing with day in and day out but with political ideology as well.”

As an example of this, Mix pointed toward the International Brotherhood of Teamsters releasing a poll showing that the majority of its members supported then-former President Donald Trump in the lead-up to the 2024 election but opted not to endorse any candidate for president.

The IUOE did not respond to the Washington Examiner’s request for comment.