Bruce Blakeman sat inside the Cherry Valley Country Club in Garden City last year as scores of Republicans played their rounds on the green. A local political fundraiser was in full swing just weeks before he was reelected as Nassau County executive.

But Blakeman's sights were already set on becoming governor.

"Every politician has that dancing around their head," he said. "If you've been elected village trustee, you think, 'Oh, maybe one day I might be the president of the United States.' "

Relentless ambition is par for the course for Blakeman, 70, whose pursuit for higher office began in 1993 campaigning for Hempstead town council. He went on to run for state comptroller, mayor of New York City, the U.S. House and the U.S. Senate.

Now Blakeman is challenging Gov. Kathy Hochul, making regular trips upstate and painting her as a "radical liberal" as he fights to narrow a deficit in the polls of as much as 16 points.

"I ran races that nobody else would run because the odds were significantly against me," Blakeman told Newsday. "You question from time to time whether you would be better off just making a lot of money and relaxing, but ... my goal has always been to have an interesting life."

Blakeman's breakthrough came in 2021, when he defeated incumbent Democrat Laura Curran for county executive by less than 1% of the vote. President Donald Trump, a fellow Republican, had just finished his first term, and Blakeman became a local champion of Trump's policies, from immigration to transgender issues.

Nassau County Executive Bruce Blakeman, center, announces new ICE enforcement measures on last year in Mineola.

Blakeman, in Trump's words, became "MAGA all the way."

But hitching his wagon to Trump was a calculated political move, said Jay Jacobs, the state and Nassau Democratic Party chairman.

"Like many Republicans, [Blakeman] was more moderate previously. ... But they take this opportunistic approach. They see that Trump is powerful. They see the only way to attain or maintain power is to cozy up to Trump, and he’s done that with vigor."

In the race for governor, a big challenge for both candidates will be staying true to the constituencies that have gotten them where they are, while wooing more centrist voters needed to win a statewide election in New York.

Proximity to Trump would only work if Blakeman "moves to Alabama," Jacobs said. "If he wants to run for governor of New York, it’s a non-starter."

Blakeman has historically taken moderate positions, even splitting from his party at times over the years. While 57% of Republicans and 71% of conservative Republicans say abortion should be illegal, according to Pew Research, Blakeman is pro-abortion rights. It's a decision he says is "between a woman and her doctor."

Blakeman after being named the Republican candidate for Senate at the New York State Republican convention in 2010.

He also bucked Republicans in 2017 to endorse Democrat Laura Gillen for Hempstead supervisor over his party's pick, Tony Santino.

"It was something that everybody counseled me not to do, but I felt strongly about it," Blakeman said. "Everybody said I’d be the pariah of the Republican Party, that the Republican Party would never forgive me and that I was destroying my career. And, last time I checked I’m running for governor on the Republican line."

Defending strongly held beliefs has defined Blakeman for decades, his colleagues and friends told Newsday. As former Hempstead Supervisor Greg Peterson put it, "I don’t think Bruce will ever be in lockstep with anybody. He has his own way of thinking."

Roots in an Island Park canal

Blakeman's personal story is as local as his political roots. His parents met where most bachelors don't think to find love: underwater in an Island Park canal.

“[My mother] couldn’t afford a bathing suit, so she jumped into the canal with her clothes on and my father thought she was drowning," Blakeman recalled. "He went to save her, and that’s how they met."

Both of Blakeman's parents served in World War II. His mother, Betty, was a surgical technician and his father, Robert, was a sailor on gasoline tankers, later becoming a state assemblyman.

Blakeman was raised in Valley Stream with one brother and three sisters, one of whom he calls "the good Cathy," a dig at Hochul, who spells her first name with a "K."

Growing up, he was popular with everyone, he said, including "the jocks, the hippies, the greasers." He played basketball at Valley Stream South High School and served on the youth council.

"I got a draft card when I was 17," Blakeman once told Newsday. "I considered going into the military, but that was just at the very end of the Vietnam War and the military was kind of in turmoil. I decided to go on to college, but ... it’s something that I regret."

During summers he worked as a janitor, dishwasher, busboy and garbage collector, a working-class resume he has touted in campaigns dating back to 2009. "My parents were very strong on work ethic. ... You had to have a summer job," Blakeman said.

But his summer gigs weren't what kept the lights on. Blakeman comes from "a very wealthy family," said Fran Becker, a longtime family friend who served with Blakeman on the inaugural Nassau County Legislature in the mid-1990s.

Blakeman’s late uncle Royal was a prominent entertainment lawyer and former president of the National Academy of Television Arts and Sciences, which distributes the Emmy Awards. Blakeman's father, Robert, after leaving office, bought Franklin Hospital Medical Center, selling it to Northwell Health in the 1990s.

Blakeman began to take his own steps into public life as a student at Arizona State University, where he was president of the Republican club.

At the 1976 Republican National Convention in Kansas City, while working for the Gerald Ford campaign, Blakeman "realized that Ronald Reagan would make a better president. ... I said to myself, if he ever runs again, I’m going to support him."

In 1980, he became a driver and aide to former First Lady Nancy Reagan.

When Blakeman entered public office in the late 1990s, he spent his days working to gain respect for the Nassau County Legislature as presiding officer — going head to head with former Nassau County Executive Tom Gulotta over taxpayer dollars, Becker said. But in his private life, he enjoyed the finer things.

"Bruce had a very expensive Jaguar, or something like that," Becker said. At one point, "one of the [Republican] leaders told him, ‘No, you can’t drive that around here. These are middle-class people.’"

Blakeman once wined and dined Nassau legislators at the elite, members-only Friars Club in Manhattan, he added. In its heyday, the largely male club hosted the likes of Johnny Carson and Frank Sinatra.

Between stints in public office, Blakeman worked as a business consultant and real estate lawyer.

In 2001, former Gov. George Pataki appointed Blakeman to the Port Authority board, where he helped lead the agency in recovery efforts and debris removal in the aftermath of 9/11. He had also recently joined the New York Guard, a volunteer force that supports the National Guard, to "make somewhat of amends" for not serving in the military, he said — standing post at Ground Zero in the aftermath of the national tragedy.

Blakeman became the Republican candidate for Senate in 2010.

Blakeman now lives in Atlantic Beach with his wife, Segal Blakeman, a Nassau family court judge. They have two kids, through her first marriage, and three grandkids.

Blakeman also shares a son, Arlen, with his first wife, Nancy Shevell, who is now married to Paul McCartney. His separation from Shevell was swift and amicable, he said, calling it a low-drama "celebrity divorce."

Political beginnings

Blakeman’s father didn’t hold back in pushing his son to run for countywide office.

In 1995, Nassau Republican Party chair Joe Cairo, then the party’s vice chair, was walking out of the Valley Stream post office one day when he ran into the elder Blakeman. "Bruce should run for the county legislature ... and be the presiding officer," Cairo recalled him saying. "I said, ‘Yeah, you’re right. He’s got leadership qualities.’ "

After two years as a Hempstead councilmember, Blakeman was elected one of Nassau’s original legislators — and its first presiding officer — when the Nassau County Legislature ormed in 1996.

He was a passionate young man, new on the scene, "full of vim and vigor," said Joe Kearney, a former Hempstead town councilman, who later became the Nassau Republican elections commissioner and executive director of the Nassau Industrial Development Agency, a state public benefit company that supports economic development.

"He sat next to me on the town board. He would talk all the time, ask a lot of questions, and then finally, if the meetings would keep going on and on, I was tasked with saying to him, ‘Finish your question and let’s move on,’ " Kearney said.

Blakeman later rejoined the Hempstead town council in 2015, serving until he was elected Nassau County executive in 2021.

The politics gene also passed on to Blakeman’s younger brother, Bradley, a senior White House adviser to former President George W. Bush.

"Brad and Bruce are two different personalities," Becker said. "Brad is more serious ... more studious, maybe a political brainiac, whereas Bruce just loves to have a good time, loves to be with people."

More than two decades later, both brothers have ties to the president.

At his inauguration in Garden City earlier this year, Blakeman told the crowd, "My brother told me he couldn’t make it here today because he had a meeting with the president." Laughing, he added, "I didn’t believe him, so he had the president call." Brad was in the Oval Office that day for a meeting about the Tunnel to Towers Foundation, of which he is a board member.

I ran races that nobody else would run because the odds were significantly against me," Blakeman told Newsday. "You question from time to time whether you would be better off just making a lot of money and relaxing, but ... my goal has always been to have an interesting life.

Bruce Blakeman first met Trump at the opening of one of his New York City projects in the early 1990s. Years later, the president has thrown his support behind Blakeman in his campaigns for county executive and now governor.

Hochul and other Democrats have used Blakeman's relationship with Trump to fling campaign attacks, appealing to voters in a largely-blue state.

In 2024, the media portrayed Blakeman as Trump’s sidekick after he was photographed holding an umbrella over the president at a wake in Massapequa for the late NYPD Officer Jonathan Diller. Blakeman later told Newsday it was Trump who first held the umbrella over them, and the two switched roles at Blakeman’s insistence.

Two months later at a rally in the Bronx, Trump flattered Blakeman for his Hollywood looks. "If I’m doing a movie of a politician, this is the guy I have playing him," he said.

In November, Blakeman became the first Nassau County executive in 32 years to win while a member of his own party occupied the White House. He became a success story for Republicans on an election night that was largely dismal for the GOP nationwide.

Just 48 hours later, he announced his run for governor.

A bid for governor

In a state where registered Democrats outnumber Republicans more than 2-to-1, Blakeman faces an uphill battle. It doesn’t help that he’ll have to play fundraising catch-up to Hochul, or that the national Republican brand is muddied by Trump’s shaky support, experts told Newsday.

"Blakeman’s chances are slim to none, but they are not none," said Lawrence Levy, dean of suburban studies at Hofstra University. He's "a microcosm ... for Republicans all over the country. They are being dragged down by Trump’s cratering approval ratings."

Trump’s approval rating fell to 34% in May, compared to 41% for Biden at this point in his term, according to Pew Research. Polling shows Republicans in particular are pulling their support, with 56% in favor of Trump’s policies as of January compared to 67% last year.

More than half of voters nationally believe the country is "headed in the wrong direction," according to a recent Siena poll. Earlier this month, Blakeman removed references to Trump on his campaign website, Politico reported.

Bruce Blakeman, right, alongside President Donald Trump at the wake of NYPD Officer Jonathan Diller at Massapequa Park Funeral Home in Massapequa Park in March 2024.

Blakeman’s ties with Trump may prove to be an obstacle in appealing to independents and Democrats across the state, Levy said, but he can’t isolate Republicans and Conservatives in the process of winning them over.

"His biggest problem is ... that he’s a pro-choice Republican. That may help him in the general election, but ... he can’t afford to lose a single Republican vote," Levy said.

Blakeman has localized Trump’s national agenda in recent years. In 2024, he enacted the country's first post-pandemic mask ban. That same year he barred transgender athletes from playing on women's and girl’s sports teams on county property. Last year, he partnered with the U.S. Immigration and Customs Enforcement to help arrest and deport Long Island's immigrants.

While Blakeman has doubled down on his support for Trump’s mass deportation agenda, Hochul is trying to ban local partnerships with ICE, like the one in Nassau. Blakeman needs to "turn it down on immigration, and raise the volume on economic issues," Levy said.

On the fundraising front, Hochul had a near 20-fold lead over Blakeman when he joined the race. As of January, she was sitting on a pool of $20 million cash on hand compared to Blakeman’s $1.2 million.

The gap may scare off Republican donors from outside New York looking to hedge their bets, Levy previously told Newsday.

Blakeman "campaigns well, but he governs poorly," said Jacobs, chair of the state and Nassau Democrats. "He’s a three-piece suit guy that knows how to say the right things to the right audience."

'Thick enough skin'

Blakeman seems to enjoy every shade of limelight, bringing equal confidence to a small crowd as he does to a stage before hundreds of people.

At a fundraiser in February at an Elmont pizza shop, a cameraman asked Blakeman if he wanted a fork and knife to eat his mushroom slice.

"Hell, no. No Bill de Blasio moment," he replied, mocking the former New York City mayor who once stained his reputation as a New Yorker by using a fork at a Staten Island pizzeria.

"That’s how I knew he wasn’t really Italian," Blakeman joked. "In Massapequa, I call myself Bruno Blakeman."

Even beneath a public persona that's — at times — angry, Blakeman turns to humor.

He has criticized Newsday for coverage he views as unfair, naming the New York Post the "official" newspaper of Nassau County, resulting in a lawsuit from Newsday last year.

At the pizzeria that day in February, he ordered a pie for the media. "Is there poison in this?" one Newsday reporter asked.

"Oh, right," Blakeman shouted toward the kitchen, laughing. "Where’s the special Newsday pie?"

Becker, the former Nassau legislator, put it this way: "If you want to call politics a game, he has a great love for the game. ... He loves it. He loves the stage, he loves being around people. ... It’s part of his DNA."

But sitting in the Nassau County executive chambers the next day, Blakeman took a more reflective tone on his career.

"I would’ve liked to have been successful in all my races, but sometimes it doesn’t work out. ... You learn about whether or not you have the fortitude, whether you have thick enough skin to be able to repel the criticism," he told Newsday. "Basically, you learn a lot about your personality. ... I’ve become wiser, I hope."

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