ILA President Harold Daggett’s shady past and lavish lifestyle come into focus with crippling port strike

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Harold Daggett, the 78-year-old chief of the International Longshoremen’s Association, isn’t pulling any punches. It’s not his style.

“People are going to sit up and realize how important longshoremen jobs are,” Daggett said Tuesday. “They won’t be able to sell cars. They won’t be able to stock malls. They won’t be able to do anything in this country without my f***ing people. And it’s about time they start realizing it.”

International Longshoreman’s Association President Harold J. Daggett speaks to union workers at the Port Newark/Elizabeth-Port Authority Marine Terminal complex on Tuesday, Oct. 1, 2024, in New Jersey. (AP Photo/Stefan Jeremiah)

The white-haired, acerbic, profane-laden leader is in his fourth term as union president. He is leading thousands of men and women into the organization’s most militant stance yet against port operators following decades of fierce contract negotiations with ocean carriers. 

Daggett, who often shows up to sit-down interviews in muscle shirts, gold chains, and large medallions, is throwing himself into the fight of his life — to win a historic pay raise and stop automation in its tracks.

On Tuesday, he was at the Port Authority in Elizabeth, New Jersey, wearing a blue sweatshirt and a gray baseball hat. He was also carrying a bullhorn.  

“We are prepared to fight as long as necessary, to stay out on strike for whatever period of time it takes, to get the wages and protections against automation our ILA members deserve,” his raspy voice rang out. It was the ILA’s first coastwide strike in almost five decades. 

The existing contract between the union and the port operators group, the United States Maritime Alliance, which covers roughly 45,000 longshoremen, expired on Monday. Negotiations have stalled since June, when, citing the use of labor-saving technology at the port in Alabama, the ILA broke off talks.

Daggett is gunning for a 77% pay increase over six years. That would boost the base hourly rate for dockworkers to $69 from $39. Port employers and ocean shipping companies initially offered nearly 40%. Under pressure from the White House on Monday, they increased their offer to 50%.

Daggett said no deal and vowed the strike would continue until employers meet his demands.   

International Longshoreman’s Association President Harold J. Daggett, center, speaks to union workers at the Port Newark/Elizabeth-Port Authority Marine Terminal complex on Tuesday, Oct. 1, 2024, in New Jersey. (AP Photo/Stefan Jeremiah)

During a recent “candid conversation” posted on YouTube, Daggett said it “wasn’t fair” that companies are “making billions of dollars” off the backs of workers.

“We brought them to where they are and now they want to get rid of us?” he said. “That’s not fair. That’s not fair at all. And this union has been around close to 200 years, so you can see why I am always fighting.” 

Those closest to Daggett say he is the heart and soul of the union and has positioned himself as the working man’s hero. They said he wants to cement his legacy with this last contract. The union has already dedicated a statue to him outside their headquarters in New Jersey. 

But there are others who say Daggett’s words don’t really match his actions or his lifestyle and that his everyman routine is all an act. 

For starters, while union workers are trying to make a living wage to support their families, Daggett is living the good life. 

Just last year, he raked in $728,000 in compensation from the ILA. He picked up another $173,000 as president emeritus of a local union branch and lives in a $2.4 million 7,136-square-foot house on a 10-acre lot in Sparta, New Jersey, according to property records and labor department filings. 

He’s also got a house in Highland Beach, Florida, that was assessed at $1.4 million in 2023, according to Newsweek

His $728,000 annual compensation is $428,000 more than his fellow union bosses at the AFL-CIO, Teamsters, and autoworkers unions, according to a tally by Politico.

Daggett has also been known to drive around town in a Bentley and owns yachts. Even Elon Musk called him out on his lavish lifestyle.

“Dude has more yachts than me!” the Tesla and SpaceX CEO tweeted. 

Daggett also has some peculiar bedfellows. 

He was accused by the Justice Department in 2005 of being an associate of the Genovese crime family, one of the original “Five Families” that dominated organized crime in New Jersey and New York and made up the “American Mafia.” He was charged with being part of a RICO conspiracy. A jury found him not guilty on several of the charges. 

His coziness with former President Donald Trump has also been making the rounds. Social media users shared a picture of him and Trump from a meeting in November. The images themselves were pulled from a July post on the union’s website following the assassination attempt on Trump in Pennsylvania. 

In the post, Daggett recalled a 2023 meeting with Trump where the former president appeared to express support for the Longshoremen.

“We had a wonderful, productive 90-minute meeting where I expressed to President Trump the threat of automation to American workers,” Daggett said. “President Trump promised to support the ILA in its opposition to automated terminals in the U.S. Mr. Trump also listened to my concerns about Federal ‘Right To Work’ laws which undermines unions and their ability to represent and fight for its membership.”

The strike began just days after Trump admitted to avoiding paying overtime at a rally in Erie, Pennsylvania. 

“I know a lot about overtime,” he said. “I hated to give overtime. I hated it. I’d get other people, I shouldn’t say this, but I’d get other people in. I wouldn’t pay.”

Daggett claimed his post with Trump had more to do with their background than any endorsement of his policies. Trump and Daggett are the same age and are from Queens. 

Daggett spent his childhood in Queens, where he was once a port worker himself. He began his longshoreman career as a mechanic after leaving the Navy and worked his way up to foreman. 

In 1967, he joined the union and over the next 57 years has served in various roles, including as the secretary-treasurer of union branch Local 1804-1 in New Jersey and as a wage scale delegate. 

He became president of the ILA in July 2011.

Within his first seven years as international president, Daggett negotiated two major contracts that keep union members among the best-compensated blue-collar workers in the country. His signature achievements in each of these six-year contracts included “protecting ILA members’ jobs and futures by blocking any ILA ports from the ravages of automation.” 

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“President Daggett has promoted men over machines and pledged that ILA workers would always out-produce automated equipment,” the union boasted on its website. 

In his personal life, Daggett has three children as well as six grandchildren and two great-grandchildren. His son, Dennis, is an executive vice president of the ILA.

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