It was four years ago Sunday, political aides to Gov. Charlie Baker confirmed what had been an open secret. The Swampscott Republican was indeed going to run for a second term. The news set the 2018 gubernatorial race into motion, which culminated with Baker cruising to re-election without really breaking a sweat. He's currently mulling whether to go for a third term in 2022.
Baker gets a bit prickly whenever he's asked the question that's on a lot of people's minds. Are you going for a third term?
"I don't understand why you're in such a big hurry for me to make a decision about this," Baker told reporters at a press availability earlier this month. While shrugging off questions about his political plans, he said he's still considering three big questions.
"The first one is, do you believe you have something productive and helpful to say? Do you have the desire and the commitment to serve the people of the constituency that you represent? And do you believe that this is something you want to spend the next few years of your life working on if you are fortunate enough to succeed?" he explained at the time.
Baker concedes that, since his previous bids for office, voters know even more about what a Baker administration is like.
"The people of Massachusetts have had a chance to take a good look at the lieutenant governor and myself over the course of the previous seven years," he said. "And if we believe that we can continue to do the work to make this state better and stronger as we work our way out of this recovery in a post-COVID 19 world, I'm sure they'll be interested in what we have to say."
"I don't understand why you're in such a big hurry for me to make a decision about this."Charlie Baker
People close to the governor say he does love the job, and while governing during the pandemic presented him a lot of headaches, he genuinely appears to be enjoying himself.
He seems proud of his record thus far, and may fear that his work over the past two terms could be un-done by his successor, should he not run again.
But there are also factors that could lead him to decide not to run.
At 65, he has to also be asking himself if it's time to cash out, and enjoy retirement with his wife Lauren while both are reasonably young and healthy.
Not running for re-election would likely bring an end to various protests and demonstrations that have popped up on Monument Street outside the Baker home.
Or after eight years on what would be considered a meager salary for a CEO in the private sector, hang out his shingle as a consultant or corporate board member, and bring in some big bucks to the Baker household.
Republican strategist Rob Gray said whatever he decides, Baker controls this race and could wait until February to declare when nomination papers become available.
"He probably won't go quite that far. But there's certainly an element of the longer he waits, the more he freezes out the attorney general, Maura Healey, who's probably his toughest opponent," Gray said. "She seems to be waiting for Gov. Baker. And that would put her off to a very late start if Charlie Baker doesn't announce until January."
If Baker does decide he's going for a third term, he will have other decisions to make about a path to victory.
The state Republican party has shifted to the right since Baker was first elected in 2014, and is more reflective of Donald Trump than of Baker's brand of Republicanism.
Gray said Baker has to be somewhat concerned about the candidacy of former state Rep. Geoff Diehl, who has already picked up an endorsement from the former president.
"There's some polling out that shows that Geoff Diehl is pretty strong with the Republicans in a Republican primary, and that Charlie Baker is far less popular with Republicans in a really odd twist than he is with independents and Democrats," Gray said. "So that's highly unusual, and it certainly has to be a concern for Gov. Baker that, in a very small Republican primary, could Diehl get him because so few votes are required."
One potential option for Baker would be to skip the Republican primary, and run in November as a third party independent.
To do so, he would need to unenroll as a registered Republican by March 8, and then gather 10,000 signatures by early August, a seemingly easy task for Baker.
But Gray thinks Baker should remain a Republican, adding there's no guarantee should Baker switch to independent.
"Three-candidate races are very unpredictable," he said. "They can get very lopsided and out of whack, so I'm not sure that Charlie Baker wants to be in that situation. He'll probably only go there if he's forced to, if that's really, he thinks, the clear path to winning a third term."
Either as the Republican nominee, or an independent third party candidate, Baker will still need to bank on unenrolled and registered Democrats to give him a third term in November.
He remains popular with those voters, including state Rep. Chris Markey, a centrist Democrat from Dartmouth.
"There are things that he has done that disgruntled some Republicans and he's done some things that have disgruntled some Democrats," Markey said. "But I think, in the end, that's what good government is. Focusing on the middle and trying to balance out everything. And he has just done a tremendous job of that."
Baker campaign advisor Jim Conroy said the governor still has not yet made up his mind about going for a third term.
But with the calendar about to change to an election year, Baker will not be able to slough off questions about his future plans much longer.