The dark past and lavish lifestyle of ILA president Harold Daggett comes into focus with a crippling port strike |

Harold Daggett, the 78-year-old chief of the International Longshoremen’s Association, makes no bones about it. It’s not his style.

“People are sitting up and realizing how important longshoreman jobs are,” Daggett said Tuesday. “They won’t be able to sell cars. They can’t supply shopping centers. They won’t be able to do anything in this country without my damn people. And it’s time for them to realize that.”

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

Daggett, who often appears in muscle shirts, gold chains and large medallions for sit-down interviews, is embarking on the fight of his life: winning a historic pay raise and putting a stop to automation.

On Tuesday, he was at the Port Authority in Elizabeth, New Jersey, wearing a blue sweatshirt and a gray baseball cap. He also had a megaphone with him.

“We are prepared to fight for as long as necessary, to continue striking no matter how long it takes, to get the wages and protection from automation that our ILA members deserve,” his hoarse voice said. It was the ILA’s first coast-wide attack in nearly five decades.

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

Daggett aims for a 77% wage increase over six years. That would increase the base hourly rate for longshoremen from $39 to $69. Port employers and shipping companies initially offered almost 40%. Under pressure from the White House, they increased their offer to 50% on Monday.

Daggett said there was no deal and promised the strike would continue until employers met his demands.

During a recent “candid conversation” on YouTube, Daggett said it “wasn’t fair” for companies to “make billions of dollars” off the backs of employees.

“We got them 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 for almost 200 years, so you can see why I always fight.”

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 latest contract. The union already has a statue dedicated to him outside their New Jersey headquarters.

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

For starters, Daggett lives the good life while union workers try to earn a living wage to support their families.

Just last year, he collected $728,000 in compensation from the ILA. He earned another $173,000 as president emeritus of a local union chapter and lives in a $2.4 million, 7,136-square-foot home on 25 acres in Sparta, New Jersey, according to property records and Labor Department files.

He also has a home in Highland Beach, Florida, which was valued at $1.4 million in 2023, according to Newsweek.

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

Daggett is also known to drive around town in a Bentley and to own yachts. Even Elon Musk spoke to him about his lavish lifestyle.

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

Daggett also has some special bedfellows.

He was accused by the Justice Department in 2005 of being a member of the Genovese crime family, one of the original “Five Families” that dominated organized crime in New Jersey and New York and formed the “American Mafia.” He was accused of being part of a RICO conspiracy. A jury found him not guilty of some of the charges.

His friendship with former President Donald Trump is also making the rounds. Social media users shared a photo of him and Trump from a November rally. The images themselves come from a July post on the union’s website after Trump’s assassination attempt in Pennsylvania.

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

“We had a wonderful, productive 90-minute meeting in which I expressed to President Trump the threat of automation to American workers,” Daggett said. “President Trump pledged 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 that undermine unions and their ability to represent and fight for the membership .”

The strike began just days after Trump admitted he would not pay overtime at a rally in Erie, Pennsylvania.

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

Daggett claimed that 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 longshoreman himself. He started his career as a longshoreman as a mechanic after leaving the Navy and worked his way up to foreman.

He joined the union in 1967 and over the next 57 years served in various positions, including as secretary-treasurer of the union branch Local 1804-1 in New Jersey and as a pay scale delegate.

In July 2011 he became chairman of the ILA.

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

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“President Daggett promoted men over machines and promised that ILA workers would always exceed the production of automated equipment,” the union boasted on its website.

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