But while Bush has tried to carve out a lane as a business-oriented outsider with moderate instincts, early polling suggests Republican primary voters are gravitating toward candidates more closely aligned with Trump-style politics. A recent University of New Hampshire poll found Charles leading the field with 37% support, followed by Bush at 18% and Midgley at 11%. Another poll modeling Maine’s ranked-choice voting system showed Charles ultimately defeating Bush 59% to 41% after redistributed ballots.

Mike Leavitt, a Maine Republican strategist and founder of Red Maverick Media, said Charles has clearly emerged as the front-runner heading into the final days of the race.

“Bobby Charles is in the driver’s seat,” Leavitt said. “The question is what impact ranked-choice voting is going to have.”

Another Maine Republican operative questioned whether public polling has accurately captured the dynamics of the race, arguing that surveys may overestimate support for Bush because they rely on inflated samples of unenrolled voters.

“Bush has very little on-the-ground support,” the operative said, speaking on condition of anonymity to discuss the race candidly. “He’s got name recognition, and he spent a ton on TV, but he is not going to win the Maine Republican primary.”

Maine’s ranked-choice voting system, first approved by voters in 2016 and reaffirmed in a second referendum two years later, allows voters to rank candidates in order of preference. If no candidate wins a majority outright, lower-performing candidates are eliminated and their votes redistributed until someone crosses 50%. Several Republicans interviewed for this story also cautioned that Maine’s ranked-choice voting system makes the primary unusually difficult to model, particularly because supporters of lower-performing candidates could ultimately decide the winner through redistributed ballots.

Leavitt said Bush may struggle to consolidate support beyond his initial base.

“His high watermark is probably going to be the first ballot,” Leavitt said. “I think it’s going to be very difficult for him to garner second-ballot votes.”

Charles, a former Reagan and Bush administration official, has run a staunchly MAGA-aligned campaign focused on immigration, crime, and opposition to Democratic policies. Despite positioning himself as one of the most pro-Trump candidates in the race, Charles has not secured Trump’s endorsement. Former House Speaker Newt Gingrich recently endorsed him, comparing Charles favorably to Trump.

Bush, meanwhile, has leaned heavily into his outsider image rather than his political lineage. In campaign ads, he jokes about voter skepticism toward the Bush family name.

“I know what you’re thinking, not another Bush,” the candidate says in one ad. “But hear me out.”

He has emphasized his business credentials, highlighting the relocation of his healthcare technology company, Athenahealth, from Massachusetts to Maine in 2007, a move that brought roughly 1,000 jobs to the state. Bush has also poured substantial personal resources into the race, raising roughly $1.3 million and contributing nearly $877,000 of his own money.

Still, some Republicans argue Bush is an imperfect test case for whether a more establishment-style Republican can still succeed in today’s GOP.

“I get the framing that this is a Bush in a Trump era,” said a Maine Republican strategist familiar with the race who spoke on background to discuss internal GOP dynamics candidly. “But the idea of Jonathan being the test subject to this is really not a fair study, because he’s such an incredibly flawed candidate.”

The strategist pointed to past domestic violence allegations involving Bush that resurfaced after divorce filings became public years ago, in which the candidate acknowledged assaulting his ex-wife. Bush later resigned from Athenahealth after the filings became public. Bush’s ex-wife, Sarah Selden Bush, has since publicly defended him and endorsed his campaign.

“Jonathan is a loving father. A man of decency who cares deeply about the state of Maine,” she said in a statement released by the campaign. “I support him and I hope the people of Maine will too.”

The strategist argued Bush’s political struggles stem from both the ideological direction of Republican primaries and his own personal baggage.

“The more establishment sort of anti-Trump candidate is not going to win,” the strategist said. “But it’s also complicated because he’s got these things in his past that I don’t think he could survive in a general election with.”

Mark Brewer, a political science professor at the University of Maine, said Bush represents a style of Republicanism that has largely faded from prominence nationally.

“If you’re looking at the Republican Party nationally, the old establishment wing represented certainly by George H.W. Bush is really kind of persona non grata within the party anymore,” Brewer said.

Brewer said Maine Republicans historically differed from the national GOP because the state long supported a more moderate, Northeastern brand of Republican politics associated with figures such as Sen. Susan Collins and former Sen. Olympia Snowe.

But the Maine GOP has in recent years increasingly embraced a more populist, Trump-aligned identity. Former two-term Republican Gov. Paul LePage, a populist Tea Party-era conservative, remains popular and is the presumptive nominee for Maine’s 2nd Congressional District.

“LePage likes to say that he was Trump before Trump,” Brewer said. “And I think if we look at the last 15 years of the Republican Party in Maine, it’s definitely changed.”

That evolution, Brewer said, has made it harder for candidates similar to Bush to win Republican primaries, even in blue-leaning states where moderate Republicans historically performed well.

“Bush is really the only one that fits that traditional establishment-type Republican model in whole,” Brewer said. “I think he’s got a tough road to come out of this primary.”

Leavitt, however, cautioned against viewing the race strictly through a “Bush versus MAGA” lens, arguing the dynamics are also being shaped by broader changes in campaign strategy and media consumption.

“I think it’s really a transition away from traditional campaigns that have primarily been done on television,” Leavitt said. “Bobby Charles’s campaign has been heavily focused on digital and social media, and they’ve done a heck of a job.”

Bush and allied groups have spent heavily on television advertising throughout the race, while Charles has relied more heavily on digital outreach and social media messaging.

Regardless of who wins the GOP primary, Republicans remain optimistic about their chances of flipping the governor’s mansion in November.

Unlike the primary, Maine does not use ranked-choice voting in gubernatorial general elections because of constitutional restrictions, meaning a candidate can win with only a plurality of the vote. An independent candidate, former state Sen. Rick Bennett, is also expected to run a competitive general election campaign, possibly reshaping the race.

“The person that wins this race for governor is going to win it with a plurality, not a majority,” Leavitt said.

MAINE’S BIPARTISAN BRAND OF POLITICAL NEPOTISM

He added that Maine’s political culture is often misunderstood by national observers who view the state strictly through a partisan lens.

“There’s really an independent streak here,” Leavitt said. “People in Maine don’t like being told what to think or do by people ‘from away.’”