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Trump likes Diehl. He also likes the Yankees. Could this be Trump’s least relevant endorsement?

Baker has not said if he will seek a third term

Former president Donald Trump.Ben Gray/Associated Press

In any other state and in any other election, an endorsement from Donald Trump is the single biggest moment in a Republican primary, whether the election is for a new senator or the town dog catcher.

Candidates for Congress in Wyoming were literally flying to New Jersey over the summer to meet with the former president at his county club, as if gaining Trump’s endorsement was a reality television show.

In Massachusetts? Trump’s endorsement of Geoff Diehl for Massachusetts governor will be about as popular as Trump’s endorsement of the Yankees.

Massachusetts isn’t a Republican state. And next year’s race for governor may feature a popular Republican incumbent who benefits from shunning Trump, should Charlie Baker seek a third term.


In one sense, the choice is clear for Trump. There’s no love lost between him and Baker.

Baker famously said he didn’t vote for Trump in either 2016 or 2020. And the feeling is mutual.

“Baker is definitely not an American First or Make America Great Again kind of guy,” Trump said in his endorsement statement of Diehl, in which he blasted Baker over everything from green energy to the MBTA.

Diehl, on the other hand, endorsed Trump shortly after the 2016 New Hampshire primary and served as a Trump surrogate in Massachusetts. Diehl says he is a Trump Republican. On Monday, he even spouted Trump-like, baseless claims about election integrity in Massachusetts.

That Trump prefers Diehl over Baker should surprise no one. What should surprise everyone is that Trump would be willing to weigh in on a Republican primary that, at least for the moment, looks like a helpless cause.

Trump faced the same crystal clear choice in 2018 when Diehl was the Republican nominee against Elizabeth Warren in her Senate re-election race, months before she decided to run for president. Warren was arguably Trump’s chief Democratic antagonist at this time, frequently sparring with him over Twitter. Warren beat Diehl by 24 points. Notably, Trump didn’t endorse Diehl in that race.


Trump had a reason to not back Diehl then. He cared a lot about his win-loss record for endorsements. This time, Trump appears more motivated by settling scores. He is, after all, making endorsements against or otherwise attacking Republican incumbents like Georgia Governor Brian Kemp, Alaska Senator Lisa Murkowski, and, as mentioned above, Wyoming Representative Liz Cheney, three politicians who stood prominently against him as he tried to contest his 2020 election loss.

For the next six months in this contest, two things matter: Baker’s decision to run, and whether Diehl can compete with him financially. Trump might be a part of how Diehl does that, but right now this is a race where the Trump factor is about as small as it has ever been since he became president.

James Pindell can be reached at Follow him @jamespindell and on Instagram @jameswpindell.