“[Lewandowski] traveled the country twice in two campaigns with Donald Trump and kind of built that barnstorm, grassroots-energizing campaign,” former Massachusetts GOP political director John Milligan said in an interview. “Diehl is likely hoping he can recreate that here.”
But this is still Massachusetts, and in a state where general-election voters have repeatedly and overwhelmingly repudiated Trump and candidates who trumpet his brand, Diehl’s latest move is head-scratcher.
“He thinks he is going to have some sort of star power if he calls in the big guns,” former Massachusetts GOP Chair Jennifer Nassour said of Diehl in an interview. “The more he talks about Trump and brings in Trump people, the less chance he has of wooing those folks that are in the middle.”
Appealing to the middle is key in a state where independents make up more than half of registered voters and have routinely helped send moderates from both parties to the corner office on Beacon Hill. Even Democratic state Attorney General Maura Healey read the room and ditched her progressive prosecutor past in favor of a more middle-of-the-road, economy-focused message when she entered the governor’s race last month and immediately became the frontrunner.
This wasn’t always Diehl’s path. He initially pivoted away from Trump when he launched his campaign in July, deflecting questions about the former president’s conspiracy theories about the 2020 election and saying he’d “rather leave national politics out of this race.”
But Diehl was already starting to trend toward Trump behind the scenes, bringing on prominent Massachusetts Trump supporter Amanda Orlando — a fellow GOP state committee member and ally of Trump-touting state party Chair Jim Lyons — as campaign manager.
A few months later, faced with the prospect that Baker might actually seek a third term, Diehl dove headfirst into Trump World with an endorsement from the former president himself.
“Everything [Diehl] has done for the last year was contingent upon the expectation of a primary fight between him and Charlie,” GOP state committee member Mike Valanzola said.
But Baker bowed out in December, creating a power vacuum. And Trump hasn’t exactly come through for Diehl since.
The former president publicly danced on Baker’s political grave in a statement that failed to mention Diehl by name. And his endorsement hasn’t opened the floodgates of campaign cash, either. Diehl is still trailing all three Democrats running for governor in monthly fundraising hauls while Healey is outraising the entire field by orders of magnitude.
Diehl isn’t ditching Trump because, in part, he’s still got a Republican primary to get through and a vocal pro-Trump faction of a deeply divided state party he’ll need in his corner to secure the GOP nomination.
There’s also a new moderate Republican in play: Chris Doughty. The wealthy investor is relatively unknown compared to Diehl — who launched an ill-fated campaign against Democratic Sen. Elizabeth Warren in 2018 — but he’s already winning support from GOP state lawmakers and is expected to at the very least make Diehl work for the party’s blessing.
Enter Lewandowski. Despite being dumped from Trump’s old super PAC and cut off by South Dakota Gov. Kristi Noem after he allegedly made unwanted sexual advances toward a Trump donor at a charity event, the former aide still carries some weight in his native Massachusetts.
“Corey is an incredibly talented campaign strategist,” said GOP state committee member Amy Carnevale, who worked across from Lewandowski on Capitol Hill in the early 2000s. “And his roots in the Bay State run deep.”
Still, Carnevale said hiring Lewandowski is “perplexing” and sends a clear message that Diehl’s campaign is “very much focused on winning the primary election and has not shifted into a general election mode.”
It’s mathematically impossible for Republicans to win a statewide general election in Massachusetts without support from independent voters and even some Democrats. Baker, for instance, polls better with Democrats and independents than among his own party.
And general-election voters in Massachusetts have little love for Trump. The state gave him barely one-third of the vote in both of his presidential runs.
“[Diehl’s] got plenty of issues to run on that would appeal to independents and middle-of-the-road voters — inflation, energy prices, the Biden administration’s failure to reign in Covid like they said they would,” said Colin Reed, former campaign manager to former Massachusetts GOP Sen. Scott Brown.
“He’s got so much to work with,” Reed, who also served as an aide to Sen. Mitt Romney (R-Utah), added. “Yet he’s running a campaign seemingly grounded in the past.”
Diehl’s continued embrace of Trump also opens a door for Healey, who built up her reputation in part by repeatedly suing the Trump administration, to regain the foil she lost when the president left office.
“With Corey Lewandowski in the fold, it is even clearer that Mr. Diehl’s agenda is fueled by hate and division,” Healey blasted out in a statement Wednesday saying the contrast between her and her Republican foe “could not be more stark.”
To Diehl, Lewandowski is a “key advisor to have in running this campaign,” he said in a statement. And he paired Lewandowski’s hire with the announcement that former New England Patriots lineman Fred Smerlas and his wife, Kristy, would serve as fundraising co-chairs for his campaign. Smerlas crossed paths with Diehl on the Trump fundraising circuit years ago and has in the past toyed with running for office himself.
GOP activists say Lewandowski, who has access to national-level donors, could also help bring in the money Diehl will need for the primary and potentially against Healey, the likely Democratic nominee who’s already sitting on more than $3.9 million, in a general election.
“Like him or hate him, he’s a nationally recognized name that gives some form of legitimacy to Geoff Diehl’s campaign,” Valanzola said. “You can argue it comes with more harm than good, certainly with the ties to Trump. But Corey’s not stupid.”
