Hi everyone, this is the first edition of The Tea Party, a (hopefully regular) newsletter in which I dig into the past, present, and future of Massachusetts politics. Today, I’m breaking down Maura Healey’s prospects of breaking a decades-long curse haunting our attorneys general.
The Curse
On November 8, 1966, voters across the nation went to the polls for what would be the only midterm election of Lyndon B. Johnson’s presidency. In Massachusetts, voters elected Attorney General Ed Brooke (R) to the U.S. Senate in a landslide over former Governor Endicott Peabody (D). Brooke, 47, was the first African-American to be popularly elected to the senate. As of 2021, he would also be the last Massachusetts attorney general to win election to any higher office.
In the years since 1966, eight have been elected attorney general—seven Democrats and one Republican. The one Republican, Eliot Richardson, would later serve as U.S. Attorney General, Ambassador to the UK, and Secretary of Commerce. In 1984, seeking the Republican nomination for U.S. Senate, he lost in a landslide to businessman Ray Shamie. Richardson’s Democratic successors would have little luck as well. Of them, one lost renomination, three lost a primary for governor, two lost a gubernatorial election, and one, Martha Coakley, lost Ted Kennedy’s U.S. Senate seat.
This horrible track record—packed with shocking and embarrassing losses—has people wondering: is Maura Healey doomed to fail?
Tom Reilly, 1999-2007
The current situation we find ourselves in is perhaps most analogous to 2006, when the retirement of Governor Mitt Romney sparked a contentious Democratic primary.
In February 2005, the question of who would be the Democratic nominee appeared answered. A Suffolk/7 News poll found Reilly held a commanding lead with 41% over a field that included Secretary of the Commonwealth Bill Galvin winning 11% and former Assistant U.S. Attorney General for Civil Rights Deval Patrick taking 3%. Reilly was also the only Democrat to lead Romney in a hypothetical matchup.
Short on charisma, as Globe columnist Joan Vennochi described it, Reilly relied on his competency to make the case for his candidacy. However, the competency argument fell apart quickly.
In January 2006, it was reported he asked the Worcester district attorney to refrain from releasing the autopsy reports of two teenage sisters who died in a car crash. They were the daughters of Reilly’s friend and campaign donor. While there was no finding of any wrongdoing, Republicans accused Reilly of trying to “hush up” the investigation.
In February, Reilly selected State Representative Marie St. Fleur to be his running mate. Hours after the announcement, the Globe reported St. Fleur had been delinquent on her taxes and student loans. The next day, she withdrew from the race. Reilly, who boasted a 37/15 (+22) favorable rating in June 2005, saw it plummet to 35/33 (+2) shortly after St. Fleur dropped out.
In the months following, Reilly’s numbers would continue to slide as primary voters became taken by Deval Patrick, an African-American civil rights attorney and businessman originally from Chicago who had demonstrated exceptional oratory ability and laid out an inspiring vision for the Commonwealth. He won the party’s endorsement and never looked back, winning 49.6% of the vote in the primary. Reilly placed third with 23.1%.
Promising Signs
While history does not bode well for Maura Healey, there are a number of promising signs that she can break the half-century curse.
Tough Race Experience: Unlike Martha Coakley, Maura Healey brings experience as a tough and proven candidate. In the 2014 primary for attorney general, she faced former state senator Warren Tolman, who had the endorsement of Governor Deval Patrick, Boston Mayor Marty Walsh, all four living attorneys general, major unions, and the Massachusetts Democratic Party. Despite the glaring disadvantage on paper, Healey went on to win all but four municipalities in a 62-38 thumping.
Her Presentation: Unlike Tom Reilly, who once said politics was not his “strong suit,” Maura Healey, a former professional basketball player, seems born to be the center of attention. She presents well on TV and in person, connecting well with voters in town halls and everyday environments. It doesn’t appear likely she will call Big Papi, Curt Schilling, or any Red Sox legend a Yankees fan, dismiss the idea of shaking hands outside of Fenway Park, or say no terrorists are in Afghanistan.
A Trump Republican: The past two attorney generals who lost the general election for governor lost to Paul Cellucci and Charlie Baker. Both were palatable to a wide swath of Massachusetts voters. Unfortunately for the Massachusetts Republican Party, their sole candidate, former state representative Geoff Diehl, has claimed fraud in last year’s presidential election and received the enthusiastic endorsement of President Trump. If Healey faces Diehl, it is very unlikely she would lose to a Trump-backed candidate in a state where he only received 32% of the vote.
Areas of Concern
Did She Wait Too Long?: For months, it appeared Healey was locked in a Mexican standoff with Governor Charlie Baker. Both seemed unwilling to announce their 2022 intentions, perhaps fearing a costly showdown between the Commonwealth’s best-known constitutional officers. By the time Baker announced his retirement, former State Senator Ben Downing, State Senator Sonia Chang-Diaz, and Harvard professor Danielle Allen had been in the race for months. Speak to a supporter of any of the three candidates and they are likely to tell you Healey waited too long and Democrats deserve a courageous leader who was ready to take on the popular incumbent. If voters can be convinced of this argument, Healey could take a hit.
Can She Make The Case?: Last year, Representative Joe Kennedy III lost a senatorial primary considered his to lose. Despite polling ahead of Senator Ed Markey by double digits prior to his announcement, Kennedy struggled to articulate a convincing reason for his candidacy. He could not shake the perception that he believed he deserved the seat due to his family name. Maura Healey could have a similar problem. While she may not be a Kennedy, her status as attorney general makes her next-in-line to be governor. Massachusetts voters do not like coronations. She will have to move beyond her attorney general stump speech on taking on big pharma, Donald Trump, and the gun lobby. She will have to articulate her plans on taxes, handling the budget, and managing the recovery from the pandemic. It remains to be seen if voters will be taken by her vision or search for an alternative.
The Dark Horse Candidate: Deval Patrick was an unbelievable dark horse candidate in 2006, sweeping away the incumbent attorney general on his way to be elected governor. Sonia Chang-Diaz, Ben Downing, and Danielle Allen are all seeking to replicate Patrick’s success. Healey also faces a dark horse threat from the Republican Party. While some have written them off, former U.S. Attorney Andrew Lelling and Secretary of Housing and Economic Development Mike Kennealy remain possible candidates who have a chance of performing well in a general election.
My Prediction
While former Boston mayor and current Secretary of Labor Marty Walsh tries behind the scenes to force Maura Healey out of the race, it appears unlikely she will step aside. The opportunity to be governor does not come up often and if she were to wait four or eight more years, the door may be closed.
If Healey runs, I’d expect her to fare well and win the primary. Suburban voters like her and Democratic primaries are increasingly fought and won in their towns. Ben Downing and Sonia Chang-Diaz are certainly credible candidates but it remains to be seen if they have the support infrastructure to expand beyond their geographic bases. Maura Healey is the only candidate who can compete from Williamstown to Provincetown on day one.
She is also likely to be elected governor. Healey is popular, winning nearly 100,000 more votes than Baker in 2018. In the post-Trump era, it is unclear if Massachusetts Democrats and Democrat-leaning unaffiliated voters will trust a Republican not named Charlie Baker enough to elect him governor. While 2022 will likely be a bad year for Democrats nationwide, Massachusetts Democrats have reason to remain hopeful.
Having said all of that, predicting the future in Massachusetts politics has often proved to be a fool’s errand. Perhaps I am destined to be a fool.