Healey and Diehl are on the ballot, Healey is in the lead, but Trump is prominent in the race for governor of Mass.

The race for governor of Massachusetts features two candidates with starkly different views on former President Trump.

As a Republican state representative, Geoff Diehl latched onto Trump as soon as he walked down the Trump Tower escalator in 2015 to announce his candidacy for the White House. Consider Diehl one of the first to have been loyal to the former president since then and who welcomes Trump’s support in his long bid to become the state’s next governor.

By contrast, Democrat Maura Healey has spent much of her tenure as state attorney general suing the Trump administration. Healey isn’t just anti-Trump; she fought him several times in court and often won.

Donald Trump rides an escalator to a press event to announce his candidacy for the US presidency at Trump Tower in 2015. (Christopher Gregory/Getty Images)

The former president personally weighed in to help Diehl defeat Wrentham businessman Chris Doughty for the Republican nomination.

“Geoff is a proven fighter who successfully fends off ultra-liberal extremists,” Trump said the day before the Massachusetts primary, when he led a online rally for Diehl. He predicted that the Whitman Republican would “rule your state with an iron fist and do what needs to be done.”

Diehl does not present himself as someone who would govern “with an iron fist”. But he is proud to have been among the first Massachusetts lawmakers to endorse Trump and to have co-chaired Trump’s 2016 campaign in Massachusetts.

Trump “wasn’t just addressing your grassroots Republican, but I’m just thinking about the average American,” Diehl told WBUR.

As he sat in his campaign headquarters in Plymouth, Diehl ticked off a number of reasons why he supported Trump’s presidency. He said Trump puts American interests first, cut taxes to help businesses, opposes US involvement in foreign wars, supports “law and order” and opposes illegal immigration.

“While Trump certainly had his personal flaws, what he did as president was something I certainly supported in 2016,” Diehl said. “And I would love to come back to some sort of presidency like that in 2024.” (Trump continues to hold campaign-style rallies, but he hasn’t said definitively whether he’ll run for president again.)

Geoff Diehl speaks with protesters against vaccination proof requirements at Boston City Hall.  (Robin Lubbock/WBUR)
Geoff Diehl speaks with protesters against vaccination proof requirements at Boston City Hall. (Robin Lubbock/WBUR)

Healey is also eager to tie Diehl to Trump, knowing how unpopular Trump is in deep blue Massachusetts, where Trump has lost two consecutive presidential elections by 2-1 margins.

“We have an adversary who is Donald Trump, who is looking to bring Trumpism to Massachusetts,” Healey said the day after winning the Democratic primaries.

Healey knows enough about how to approach Trump politics.

Shortly after his inauguration, Trump imposed a travel ban from a number of Muslim-majority countries, and Healey quickly challenged the action in court.

She went on to sue the Trump administration nearly 100 times, often joining other Democratic attorneys general. His office has filed a lawsuit to protect immigrant rights, reign in predatory student lenders, fend off challenges to the Affordable Care Act and preserve environmental regulations, among dozens of lawsuits.

Healey told WBUR that after Trump’s election victory, she had no choice but to sue his administration again and again “to keep bad things from happening to the people here in Massachusetts.”

“This election has been galvanizing,” she said.

But some Republicans blame Healey for becoming the chief anti-Trump lawyer.

“Maura Healey, unfortunately, has armed her attorney general’s office,” said Jim Lyons, chairman of the state’s Republican party.

Lyons said the lawsuits were part of Healey’s political agenda, when she should have been “fighting for the people of Massachusetts.”

Healey said his office continued to do its normal legal work, even suing the federal government.

“We haven’t missed a thing when it comes to worker and consumer protection here,” Healey said.

Scott Harshbarger, a former Democratic attorney general who ran for governor in 1998, also dismissed the charge that Healey abused the power of the AG’s office by challenging Trump so aggressively in court.

“Those lawsuits were about consumer protection, environmental protection, civil rights,” Harshbarger said. “And the Attorney General – the people’s advocate – represented the broader public interest of Massachusetts.”

Maura Healey walks through Maverick Square.  during a first campaign stop in East Boston.  (Jesse Costa/WBUR)
Maura Healey walks through Maverick Square. during a first campaign stop in East Boston. (Jesse Costa/WBUR)

The two candidates also spoke about other issues in the race.

In his campaign, Healey promised to expand housing, improve transportation, lower the cost of living and protect the right to abortion. She also repeatedly attacked her Republican opponent, saying voters would face a tough choice in November.

“Geoff Diehl wants to tear people apart,” Healey said in Worcester the day after the primary. “We want to deliver for people.”

But while Healey often tries to tie Diehl to Trump, many Republicans hope Diehl can benefit from dissatisfaction with the current president.

“President Biden is on the ballot in November, not Donald Trump,” Lyons said. “And what we’ve seen are the policies of Biden and Maura Healey that are destructive not just for Massachusetts, but also for America.”

According to Lyons, Democrats will have to answer for a growing sense of economic uncertainty, high inflation and “reckless spending.” In contrast, Lyons calls Diehl a fiscal conservative who supports parental rights and law and order.

Diehl is also leading an effort to repeal a law giving undocumented immigrants access to driver’s licenses, which will be passed in November.

“I think what’s extreme are policies like rewarding people who came here illegally with a document,” Diehl said.

Still, polls suggest that Diehl is well behind Healey, just as Trump fell behind Hillary Clinton and Joe Biden on the ballot in Massachusetts in previous elections.

But Diehl and his supporters say they have passion on their side. They also point out that politics can hold surprises, even in Massachusetts. Ask Scott Brown, the Massachusetts Republican who shocked Democrats in 2010 when he won a special election to become a US senator.

Healey and his fellow Democrats are determined to avoid another surprise like that this year. And they’re hoping Trump will help make a difference in November.

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