They are either with him or against him.
The “him” being President Donald Trump.
So, any Republican running for governor in 2026, with any remote chance of victory in liberal Massachusetts, must choose to run with Trump or against him.
There is no middle ground, not with Trump and not in Massachusetts.
So that is the dilemma facing Mike Kennealy of Lexington, the first Republican to announce that he is running to unseat progressive Democrat Gov. Maura Healey in 2026.
Other potential GOP candidates will face the issue as well. Only one of them will win the Republican convention endorsement and nomination.
Hardly had Kennealy, a former member of GOP Gov. Charlie Baker’s cabinet, announced than the Democrats immediately labeled him as a Trump supporter, calling him “MAGA Mike.”
Kennealy, attempting to walk a tightrope on Trump, did not mention him in his video announcement. He has said he did not vote for Trump in the last election but would work with the Trump administration if elected.
That will not cut it among Trump’s diehard supporters who will be a major presence at the GOP convention and in the primary.
Besides, by the year 2026, Trump, a most consequential president, may have accomplished many of his goals, ranging from shutting down the border and deporting criminal illegal aliens, to bringing home thousands of manufacturing plants and millions of jobs under his tariff initiatives.
And if jobs become an issue — as it usually is — then Trump supporters could be searching for a gubernatorial candidate who is a full-throated supporter of the Trump agenda as opposed to some wishy-washy Republican.
Or they could seek out a Trump-supporting Democrat to run against and topple anti-Trump Maura Healey in a Democrat primary. That Democrat would most likely be elected in the November election in Democrat-controlled Massachusetts.
That Democrat challenger could be Massachusetts native Sean O’Brien, 53, the fiery and outspoken head of the powerful 1.3 million International Brotherhood of Teamsters, who has a solid relationship with Trump.
O’Brien last July became the first Teamster president to address the Republican national convention that endorsed Trump. He urged delegates to respect and support the American working class.
His earlier request to speak at the Democratic convention was ignored despite the union’s history of supporting Democrats and contributing heavily to their campaigns.
Following the GOP convention, the Teamsters decided not to endorse either presidential candidate, which was a victory for Trump.
O’Brien later revealed that an internal poll showed that 60% of its members supported Trump over Democrat Kamala Harris.
O’Brien, with roots in Medford and Charlestown where his father and grandfather were Teamsters, is an aggressive advocate for jobs for the middle and working class. He believes that Trump, not the Democrats, can bring those jobs back from overseas.
The outspoken Democrat labor leader, who worked his way up from the bottom of the union ladder to the top, has taken the Democratic Party to task for abandoning the labor movement and American workers.
He told the Boston Herald that he speaks to Trump three to four times a month.
“The Democrat Party is not the party I grew up in,” he said.
In 2011 Democrat Gov. Deval Patrick appointed O’Brien to the board of directors at Massport.
While battling for workers, O’Brien has also raised millions of dollars for charity, including “Light Up the Night, an annual fundraiser for children with autism.
The interesting thing is that O’Brien could run for governor as a Trump Democrat — or even run as a Republican. That’s a dilemma too. Either way, he would have the support of a grateful Trump.
Political reporter Peter Lucas can be reached at peter.lucas@bostonherald.com.
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