A pair of cufflinks worn by former President Donald Trump went for $2,000 at an auction benefiting the Maine Republican Party at its state convention in Augusta last month.
Then a pair worn by Trump’s first press secretary, Sean Spicer, who spoke to attendees, went up on the block. They went for $2,600. The buyer was a wealthy scion of one of America’s most famous families. He was making a point that few could afford and probably eluded most there.
“I was trying to establish relative market value for the room to see,” said Jonathan S. Bush, the nephew and cousin of former presidents George H.W. Bush and George W. Bush, respectively, who now lives in Cape Elizabeth after moving to Maine full time in 2021.
That was a knock on Trump. But Bush now owns the accessory of a man who owes most of his political profile to the former president. His money is also going to a party trying to secure at least one of the state’s four Electoral College votes for Trump in the November election.
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It’s illustrative of how Bush and his patrician family now fit awkwardly into the Trump-loving party. Yet the 55-year-old is trying to increase his involvement in Maine politics after a limited history as a donor. He has held meetings with officials, including Joel Stetkis, the state party chair, to discuss initiatives that he could fund to help the state party make gains.
In an interview, he called Trump “personally troubled,” espousing a goal of supporting “non-kook members of both parties.” He praised Gov. Janet Mills for keeping “the lunatic fringe” of her Democratic Party at bay. But he sounds firmly like any Maine Republican in criticizing state spending and local governance in liberal Portland and is intrigued by legislative races.
“I think there’s a giant opportunity for Republicans if they were to take a look at their positioning a little bit more,” he said. “But even without that, I think just [campaign] execution — sort of north of Freeport — could create a lot more moderation in the government.”
Bush stands out among his family for wading this deeply into Maine politics and living here full time. His relatives often held fundraisers for Maine politicians at their Walker’s Point compound in Kennebunkport. Despite their identification with the state and their family origins in the Northeast, the two presidents rose in public life while living in Texas.
Jonathan S. Bush, whose father was the late George H.W. Bush’s brother, grew up in Manhattan but spent lots of time in Kennebunkport and North Haven growing up. He established firmer ties with Maine when athenahealth, the health care tech company he founded, brought hundreds of jobs to Belfastafter buying office space in 2007 that had been vacated by MBNA.
Those jobs are still there. Bush is not. He resigned as CEO in 2018 after activist investor Paul Singer’s push to oust him from the public company intersected with reports that he confessed to physical altercationswith his ex-wife more than a decade earlier. Bush admitted to hitting her, but both said then that they had repaired their co-parenting relationship after divorcing.
Bush has remained a major player in the same industry. His startup, Massachusetts-based Zus Health, is a platform for providers that makes patient data easier to use with a goal of being the “LinkedIn of medical records,” he said.
His move to Maine coincided with the early-pandemic shift to remote work that he said finally allowed him to live here full time. He bought his oceanfront Cape Elizabeth home from former gubernatorial candidate Eliot Cutler for $7.55 million in 2021. (Just more than a year later, Cutler was arrested on child p*rnography charges.)
Bush has a reputation as a loose and unconventional boss. In an article detailing his problems with Singer at athenahealth, The New Yorker saidBush “could be goofy or ribald at times.” There were company events featuring heavy drinking, and he played drinking games while shirtless with employees and investors.
Those same traits that brought him down can also make him a likable character. When a reporter suggested continuing a conversation about Maine politics over beers sometime, Bush offered to pick him up on a speedboat along the coast and head over to North Haven.
Former Belfast Mayor Mike Hurley, who spent time with Bush while his old company was coming into the liberal-leaning city, remembers him positively as a freewheeling person who was fun to talk to with an “old-money yacht buddy” aura that belies his raising.
“If I had to put him on the hippie meter — all the way to the left is the hippie, all the way to the right is some ultra-conservative — you know, I’d put him left of center,” Hurley said.
Bush’s political history is still right of center. He has given at least $568,000 to political candidates and causes across the country since 2010, according to OpenSecrets.org data. That includes $50,000 to a political committee he formed to support former South Carolina Gov. Nikki Haley, who was Trump’s biggest 2024 primary rival.
He has given relatively little of that to Maine politicians, but he has supported Republican U.S. Sen. Susan Collins. Bush also donated to both U.S. Rep. Jared Golden, a Democrat from the 2nd District, and his Republican opponent, former U.S. Rep. Bruce Poliquin, ahead of the 2022 election.
Bush is drawn to Maine in part because he sees it as an open political playing field where the center of the electorate matters. That contrasts with his pessimistic view of national politics. Referencing Biden and Trump’s age, he said both of them “could keel over any day.”
After two Bushes in Texas lost primaries in 2022, The Texas Tribune questionedwhether it would be the end of the family’s political dynasty, quoting a political scientist who said their name is “essentially what the Romanov family name is in Russia.”
When asked if he was considering becoming a candidate in Maine, Bush demurred with a joke.
“I’m a Bush. If I didn’t think about running for office, I wouldn’t breathe. I wouldn’t be breastfed as a small child,” he joked. “So, I think about it all the time. But I also like supporting people.
“It’s fun to be excited about leaders, and we don’t get that treat all the time.”
