A pair of cufflinks worn by former President Donald Trump sold for $2,000 at a fundraising auction for the Maine Republican Party convention in Augusta last month.
Later, the shoes worn by Sean Spicer, Trump’s first press secretary, who addressed the crowd, were auctioned off for $2,600. The buyer was the wealthy scion of one of America’s most famous families, who was making a point that few could afford, and probably most could not understand.
“I was trying to establish the relative market value for looking at the room,” said Jonathan S. Bush, a nephew and cousin of former presidents George H. W. Bush and George W. Bush, who moved to Maine in 2021 and now lives in Cape Elizabeth.
That was a criticism of Trump. But Mr. Bush now has the accomplice to owe much of his political standing to the former president. His money is also flowing to the party trying to secure at least one of the state’s four electoral votes for Mr. Trump in November’s election.
It’s a good example of how awkwardly Mr. Bush and his patrician family fit into a party that supports Mr. Trump. But Mr. Bush, 55, has been trying to get more involved in Maine politics, despite his limited history as a donor. He’s been meeting with officials, including state party Chairman Joel Stetkis, to discuss efforts he could fund to help the state party grow.
In the interview, he called Trump “personally problematic” and asserted his goal of supporting “the non-knaves of both parties.” He praised Gov. Janet Mills for keeping the “fanatic wing” of the Democratic Party in check. But he is just like other Maine Republicans in his criticism of state spending and local autonomy in liberal Portland, and he has an interest in congressional races.
“If Republicans would reassess their position a little bit, I think they would have a great chance,” he said. “But even without that, [campaign] Maybe an execution somewhere north of Freeport would bring more moderates into the government.”
Bush stands out among his family for his deep involvement in Maine politics and his permanent residence here; his relatives frequently hosted fundraisers for Maine politicians on the grounds of their home in Kennebunkport’s Walker’s Point neighborhood. Despite their attachment to the state and their family origins in the Northeast, both presidents ran for office while living in Texas.
Jonathan S. Bush, the son of the late George H.W. Bush, grew up in Manhattan but spent much of his childhood in Kennebunkport and North Haven. He developed stronger ties to Maine when the medical technology company he founded, Athenahealth, bought office space vacated by MBNA in 2007, bringing hundreds of jobs to Belfast.
Those jobs remain in place today. Mr. Bush is not. Mr. Bush stepped down as CEO in 2018 after activist investor Paul Singer’s push to oust him from the company combined with reports that he had confessed to a physical relationship with his ex-wife more than a decade ago. Mr. Bush acknowledged that he had beaten his wife, but both said at the time that they had repaired their co-parenting relationship after their divorce.
Bush remains a major player in the industry: His Massachusetts-based startup, Zus Health, is a platform for health care providers to make patient data more accessible and aims to become the “LinkedIn for health records,” he said.
His move to Maine coincided with the shift to remote work early in the pandemic, which he says finally allowed him to live here full time. He bought an oceanfront home in Cape Elizabeth for $7.55 million in 2021 from former gubernatorial candidate Elliot Cutler. (Just over a year later, Cutler was arrested on child pornography charges.)
Mr. Bush was known as a freewheeling, unconventional boss. In a story detailing his troubles with Mr. Singer at Asenahealth, The New Yorker wrote that Mr. Bush “could sometimes be goofy and vulgar,” that he would drink heavily at company events and once played shirtless drinking games with employees and investors.
The same traits that brought him down can also make him likable: When a reporter suggested they meet up sometime to discuss Maine politics over a beer, Bush offered to pick him up in a speedboat down the coast and take him to North Haven.
Former Belfast Mayor Mike Hurley, who spent time with Bush when his company was expanding into liberal-leaning cities, fondly remembers him as a fun, easy-going guy who had the vibe of a “yachting buddy from an old family” that was contrary to the environment he grew up in.
“If you were to measure him on the hippie-meter, with the far left being hippies and the far right being ultra-conservative, I would place him on the left of center,” Hurley said.
Bush’s political record remains center-right: He has donated at least $568,000 to national candidates and campaigns since 2010, according to data from OpenSecrets.org, including $50,000 to a political committee he formed to support former South Carolina Gov. Nikki Haley, Trump’s main rival in the 2024 presidential primary.
While he has donated relatively small amounts to Maine politicians, he has supported Republican Senator Susan Collins, and ahead of the 2022 election, he has donated to both Democratic Rep. Jared Golden, who represents the 2nd Congressional District, and his Republican opponent, former Rep. Bruce Poliquin.
Mr. Bush is drawn to Maine in part because he sees it as an open political arena where core voters matter, a contrast to his pessimistic view of national politics, where he has said both Biden and Trump “could fall at any moment,” referring to their ages.
After the two Bushes lost the 2022 Texas primary, The Texas Tribune quoted a political scientist as saying the Bush name was “essentially the name of Russia’s Romanov family” and questioned whether that would mark the end of the Bush political dynasty.
When asked if he was considering running in Maine, Bush joked:
“I’m Bush. If I wasn’t thinking about running for office, I wouldn’t be breathing, I wouldn’t have been breastfed as a little kid,” he joked, “so I think about it all the time. But I also like supporting people.”
“It’s fun to get excited about a leader, but we don’t always get to have that fun.”
