After years of frustration, Beacon Hill progressives succeeded this week in passing legislation that they say will move the state away from a failed tough-on-crime philosophy toward what is described as a smart-on-crime approach. 

It’s not just Massachusetts lawmakers embracing a new approach to handling law-breakers. Four of the five declared candidates for Suffolk County District Attorney, running to succeed Dan Conley, supported passage of the bill.  

In fact, several of them say the law doesn’t go far enough, though they welcomed it as a step in the right direction.  

That represents quite a shift, should one of them get elected. Conley, who has opted to not run for re-election after 16 years, was one of nine DAs in the state who wrote a letter last fall to lawmakers urging them to slam the brakes on the reform bill. Only two DAs in the state declined to sign it. 

Progressives see the tide turning in their direction on criminal justice. “The bill underscores the public’s readiness for fundamental change,” says Shannon McAuliffe, one of the reform-minded candidates for Conley’s job. “Legislators are reacting to their constituents.” 

McAuliffe, like many others, suspects that Boston will follow the example of Philadelphia, which in November elected civil rights attorney Larry Krasner to be District Attorney. 

But their optimism might be unwarranted. Just as the reform bill required extensive compromise to make it through a divided legislature, voters in in Boston, Chelsea, Revere, and Winthrop might very well settle on a more cautious new District Attorney: Greg Henning, current prosecutor in Conley’s office, and the only candidate who would have voted no on the legislation. 

Barring any late entries, Henning seems to be the most conservative candidate—or nuanced, as his campaign prefers—on criminal justice reform. He is also the lone white man in the race. In the past week, City Councilor Michael Flaherty and state senator Joseph Boncore both ended speculation by announcing plans to not run for the office. Eugene O’Flaherty, Mayor Marty Walsh’s top lawyer in City Hall, also appears to have opted out.  

Henning, I learned from his campaign this week, sees “a number of positive steps” in the bill, such as making the penalties for illegally selling fentanyl much harsher than those for doing the same with marijuana. Nevertheless, he would have urged legislators to vote no without “careful revisions.” 

That aligns him with just five lawmakers in the entire legislature, all Republicans, who voted against passage Wednesday. 

A range of reactions 

The other four candidates for District Attorney all supported passage of the bill. None went as far as Democratic gubernatorial candidate Setti Warren, who announced Wednesday that he would veto the bill for creating a new mandatory minimum sentence for fentanyl and carfentanil trafficking—the provision that Henning’s campaign pointed to as a welcome change to combat the opioid crisis.  

Evandro Carvalho, a state representative and former assistant district attorney who helped craft portions of the bill, voted yes on Wednesday’s vote. Some of his proposals were kept out or pared down, but in a statement Carvalho praised the final version as “historic and sweeping.” 

Rachael Rollins, former chief legal counsel for the Massachusetts Port Authority with extensive prosecutorial experience, supports the bill, but cautions that its success lies in its implementation, says campaign consultant Scott Ferson.  

Linda Champion, a long-time prosecutor, says that she views the bill as progress and would counsel a vote in favor, although she wants to go further in eliminating mandatory minimum sentences and making young offenders eligible for pre-trial diversion programs.  

McAuliffe, a veteran defense attorney, also would have liked to see a more progressive bill. Nevertheless, she tells me that she “emphatically” supports the bill, praising in particular its approach to drug addiction among offenders. 

All four of those candidates are, in their own way, trying to capture the progressive energy for criminal justice reform that is all the rage in Democratic circles across the country these days.  

ACLU chapters and others went looking for candidates to carry the mantle in other left-leaning cities. In Boston, McAuliffe took up the cause, intending to challenge Conley from the left—when, on the eve of her announcement, he declared that he won’t run for re-election.  

Now, progressives have four intriguing candidates to choose from. Carvalho has support from six of his fellow state representatives and former US Attorney Wayne Budd; McAuliffe has been endorsed by popular sheriff Steven Tompkins and retired federal judge Nancy Gertner; Rollins has a wide network of contacts and the endorsement of the MBTA Police Association; and Champion has, among others in her corner, her ex-husband and two-time DA candidate Eddie Jenkins Jr. 

Boston would seem as ripe as any city for a reform-minded top prosecutor. Just look at November’s city elections, which placed two more progressive black women on the City Council—not to mention legislative support for the reforms in the new criminal-justice bill. 

Plus, on the day of the DA primary, half the city will also be voting in the congressional showdown between incumbent Michael Capuano and challenger Ayanna Pressley. That could bring large numbers of women, minorities, and progressive-minded voters to the polls. 

But with those voters potentially split among the four reform candidates, Henning gets to be like the Price Is Right contestant who bids one dollar more than the others. By pitching himself as progressive, but just a little less so than the other four, he can hope to lay claim to everybody from the center-left to tough-on-crime conservative Democrats. 

While Henning does not have Conley’s endorsement—at least not yet—he does have $500 of the current DA’s money. Conley is not the only member of that office who has contributed to Henning’s campaign.  

Even more striking are the number of Boston Police Department officers who have given to Henning already. They account for nearly a quarter of the $110,000 Henning has raised through the end of March. That will be seen by some voters as a strong show of support from the law enforcement community that works with Henning and other prosecutors. Others will worry that Henning would be unwilling, as DA, to challenge or provide oversight to the BPD that helped get him elected. 

Less visible in his support so far, but potentially key to Henning’s success, is Joe Kennedy III. The two attended Buckingham Browne & Nichols together, and Henning briefly served as the Congressman’s senior advisor before re-joining Conley’s office. That resume detail is omitted from the candidate’s web page, but I am assured that the two remain close. 


So, how will voters in Boston, Chelsea, Revere, and Winthrop choose in a wide-open, competitive district attorney race? 

Unfortunately for the local punditry, we have no signposts to guide us. 

Suffolk County residents have not had a truly open DA election—one without either an elected or appointed incumbent on the ballot—since 1869, when Oliver Stevens chose not to run again and John Wilder May prevailed in the subsequent election. 

Conley was appointed by acting Governor Jane Swift in 2002, when Ralph Martin left office, just as Martin had been appointed by Bill Weld when Newman Flanagan left in mid-term. Flanagan won the office in 1978 by challenging 80-year-old incumbent Garrett Byrne in the Democratic primary—winning with 40% of the vote in a three-way race with Byrne and Chris Iannella. The successions go back, and back, and back like this for nearly 150 years. 

There hasn’t even been a contested Democratic primary since 1990, when Jenkins ran unsuccessfully against Flanagan, in the racially tense aftermath of the Charles Stuart murder investigation. That was the same year that Bill Weld became Governor running on a tough-on-crime platform—and went on to enact, with the state legislature, many of the statutes that today’s legislature seeks to reform with the new bill. 

It’s a far different city now than it was then, with much different attitudes about criminal justice—but by no means unanimity of opinion.  

The current crop of candidates will give the region a much-needed airing of attitudes and arguments about those issues. Regardless of who among them prevails, the campaign should be a boon to its residents.