WOBURN — It is shortly after dawn and Kevin O’Connor, the President Trump-backing Republican candidate for Senate, is making his case to a small group of police officers behind the police station here, telling them he will do what a Kennedy could not: defeat Edward J. Markey.
“We’re going to win,” he says, not for the last time this day.
Anything is possible, but in a state poised to repudiate Trump perhaps by a 70-30 margin, O’Connor could be headed for a drubbing.
Which begs this question: Why is this 58-year-old, recently a partner at a major law firm, who lives in a well-to-do town, running a seemingly quixotic, long-shot campaign?
Markey, O’Connor said, is a senator who has taken positions that “will compromise neighborhood safety and crush our economy and kill jobs.” The longtime Democratic pol from Malden is incapable of working across the aisle, according to O’Connor. Markey’s record is beatable and O’Connor is convinced he’s the candidate to beat him.
“I understand how to identify strengths and weaknesses, how to make a case against weaknesses,” said O’Connor recently. “I understand how to work with people.”
O’Connor grew up the second of six siblings and spent parts of his youth in the New York City area and Connecticut. His father worked in journalism and his mother was a public school teacher. There was and continues to be a broad range of political opinions in the family, according to O’Connor. He says his father was a Democrat but switched parties to vote for him in the primary.
“I think it’s the party where common sense . . . has a more solid home,” he said of why he is a Republican. “I believe in safe neighborhoods, good jobs, and private sector economic growth. I believe that’s the best way to advance the human condition.”
He graduated from high school in Greenwich, Conn., where he played football with future NFL star Steve Young. He would go on to play outside linebacker for the football team at Trinity College, and said he still enjoys watching the game.
Asked about his take on the Patriots season, he gives a true politician’s answer: “It’s an interesting year. I love Cam Newton. Miss Tom Brady, love Cam Newton.”
He went to law school at Boston College, and before the campaign he was working as a partner at Hinckley Allen, where his legal practice focused on business and intellectual property litigation. He lives in Dover.
A long way from downtown Boston law offices, he’s now in the back parking lot of the police station, rattling off some internal polling that he says shows that Massachusetts voters are receptive to ousting Markey.
Dressed casually in a zip-up jumper, jeans, and boots, O’Connor raps Markey for wanting to end qualified immunity for police, saying his opponent has chosen to vilify law enforcement. He says the incumbent is not “dialed in on our issues.” In this moment in Woburn, O’Connor’s entire campaign entourage is comprised of his 18-year-old nephew and driver, Andy Moore, who is holding a box of Dunkin' Donuts coffee to give to the cops.
Similar scenes have played out throughout his campaign; O’Connor said he has visited dozens of police stations throughout Massachusetts. He called it a “systemic way to reach communities," but it’s also clearly a political calculation. O’Connor is banking on police disenchantment with progressive Democratic lawmakers like Markey amid a broad push for substantial police reform. He will later claim “we have every police officer in Massachusetts and their families.”
In his first bid for public office, O’Connor, who defeated Shiva Ayyadurai in the GOP primary, is adamant that Markey can and should be defeated. After the Woburn PD stop, O’Connor, a father of four, pointed out that Massachusetts, for all its reputation as a liberal bastion, has a history of electing GOP governors in recent decades.
He finds himself doing a strange dance: voicing support for President Trump while simultaneously trying to frame himself as an independent thinker.
The state’s current, popular Republican governor, Charlie Baker, has distanced himself from Trump. O’Connor is voting for the president, and said he thinks Trump “did a good job of creating an economy that was very inclusive.” He does not think the 45th president is racist or xenophobic. He said that he is different temperamentally than Trump, and calls himself a “Kevin O’Connor Republican."
When asked where he disagrees with the president, O’Connor said he is more “oriented to free trade than the president.”
”He’s a bull in a china shop, often," O’Connor said of Trump. “His approach is not without its downsides.”
On the morning of his Woburn visit, a stop at a Gloucester fish pier followed, and it was MAGA country. There was a lengthy parade of cars lined up on the pier with flags and signs: “Trump 2020 Keep America Great,” “Women for Trump,” “Massachusetts for Trump,” “Back the Blue.”
The parade’s participants had love for Trump, but some drew a blank when it came to O’Connor’s candidacy. The name didn’t register for Willy Eastman, a 74-year-old retired police officer from Gloucester, who was sitting in his Jeep in the line of vehicles on the pier, a “Veterans for Trump” hat on his head.
“Who’s he running against?” asked Eastman, who said he plans to vote Republican on Nov. 3.
Another person in the line, Peter Parisi, a 63-year-old Gloucester commercial fisherman, said O’Connor was on his boat recently. Parisi gave a skeptical assessment.
“He says he ain’t a Baker Republican, and he says he ain’t a Donald Trump Republican,” said Parisi. “Do we know what kind of Republican he is?”
Jonathan Ring, a 41-year-old retail worker from Rockport, is more unabashed in his support, calling O’Connor a “common-sense conservative and Republican."
”Ed Markey has been there too long," said Ring.
Framing Markey as out of touch is central to O’Connor’s campaigning. He steers most questions back to what he perceives as Markey’s failures. Markey, he said, is not a hard worker and is not in Massachusetts enough. No one, said O’Connor, has ever won statewide here running as far left as Markey.
“He’s wrapped himself in the AOC, Bernie Sanders, Democratic Socialist wing of the party,” he said.
Markey’s Green New Deal, which the senator touted throughout his Democratic primary contest with Joseph P. Kennedy III, is unrealistic and utopian, and the effect of the measures called for in that proposal would be “devastating economically,” said O’Connor.
In response to the barrage of criticism from O’Connor, a Markey campaign spokeswoman said such attacks “are desperate moves by a candidate who is desperately out of touch with the needs of the people of Massachusetts." The state’s voters, according to Markey’s campaign, will reject O’Connor because “they reject the Trump agenda.”
“We don’t have to tie our Republican opponent to Donald Trump, he’s done that all by himself,” said Liz Vlock, a Markey spokeswoman.
At the Gloucester pier, O’Connor passed on joining the Trump-supporting car parade. He gave a wave as the procession left the pier in a cacophony of honks, and made small chat with a couple of people who weren’t in the motorcade.
From there, he walked around downtown Gloucester, where both the unpredictable aspects of retail campaigning and the raw nature of this election were both featured. He said hello to a bearded man sitting on a wharf and a gruff reply came back: “Don’t call me sir, you aren’t in the army.”
He ordered lobster rolls from a food truck and mentioned to the person taking his order that he’s running for Senate. The pitch ended there.
Eventually, the motorcade of Trump supporters rolled through. O’Connor waved to some children holding Trump signs in the back of a pickup. Moments later, a man on foot screamed at the vehicle procession: “You’re all racists!”
O’Connor headed to Stage Fort Park in Gloucester for his next scheduled event. He arrived to find a gorgeous view of the harbor, but not the fish fry he was seeking. After some confusion, he headed back to the pier. People in Trump gear were tucking into grey sole and chatting.
He addressed the crowd without a microphone or bullhorn, telling people that Massachusetts voters want safe neighborhoods, good jobs, and “unity.”
“True unity,” he said. “Not cancel culture unity. Not political correctness unity. True unity rooted in liberty and justice for all.”
A yell came from the crowd: “USA!”