AT A TIME when talk of criminal justice reform is in the air, Greg Henning looks like the face of the status quo.
One of five candidates in the Democratic primary for the open Suffolk County district attorney’s seat, Henning has spent a decade as a prosecutor in the office, most recently directing its gang prosecution unit. He has the blessings of outgoing DA Dan Conley, who, with his wife, has donated $1,000 to his campaign. Henning parts ways with several of his opponents on criminal justice policies, including mandatory minimum sentences and bail reform. And he has raked in more than $60,000 in donations from police officers, a fundraising bounty that has some questioning whether he’d deal fairly with the many cases involving police. (He’s the only candidate who has said he would not appoint a special outside prosecutor to handle police-involved shootings.)
While Henning is seen widely as the law-and-order candidate in the race, Joe, a wiry 23-year-old former gang member calls him something very different. “That’s my family,” he said of Henning.
Joe, who grew up in a troubled Roxbury household, says Henning has been there for him when no one else was, including taking a day off from campaigning in April to drive out to the state prison in Shirley and pick him up when he was released following a three-year sentence for armed robbery.
You could say it was the least Henning could do for him, since he helped put Joe away for both prison sentences he has served over the last five years.
Henning has developed close relationships with several young men he prosecuted, playing both parts of the good cop, bad cop routine. It’s a side of the 38-year-old candidate that softens his image as the prosecutor backed by the law enforcement establishment. But some of his opponents in the race say his after-hours compassion stands in sharp contrast to a commitment to tough-on-crime policy positions that are increasingly coming in for scrutiny in the rethinking of criminal justice policies.
In late 2009, Henning started volunteering with College Bound Dorchester, a program that works to help offenders turn their lives toward more positive pursuits. They needed someone to tutor and coach their basketball team. It turned out the starting point guard was a young man Henning had prosecuted who served a jail sentence. Shortly after starting, Henning and the young man drove together to New Hampshire for a game.
“We just kind of talked it out,” said Henning. “It was a strange conversation because all the things you want to say to somebody that has been involved in locking you up and all the things you want to say to somebody that you had locked up – we had an hour and half to do it.”
Joe, who does not want his real name used because he’s worried about being known as a friend to the former head of the DA’s gang unit, said Henning reached out to him after their first encounter – when Henning was prosecuting him on a gun charge at age 17. “He said, after I do my time if I wanted to change my life around to reach out,” said Joe. “I’m like, this guy put me in jail, now he’s trying to help me?”
They began corresponding even before Joe got out of South Bay House of Correction. Henning helped with everything from getting him signed up for MassHealth to deal with health problems he suffers from to obtaining a state ID. But within a year of his release at age 19, Joe was facing a new armed robbery charge.
In a bizarre twist, Henning wasn’t the prosecutor in the case but a witness. He happened upon the scene of crime because he was driving through the area looking for Joe. He wound up testifying against him before a grand jury. Joe pleaded guilty before the case went to trial and was sentenced to three years in state prison.
“It was hard for me for lots of reasons,” said Henning. “When he got locked up it was him reoffending, and that was the thing I’d always been hoping that it never happened.”
“He would come visit me all the time, he wrote me all the time,” Joe said of his interactions while in prison with Henning, with whom he has stayed in close since his release this spring. “Him helping me, helped me help myself,” said Joe, who is now trying to get on track and says of his involvement in the criminal justice system, “it’s behind me.”
Henning said his volunteer work with College Bound Dorchester and early experiences reaching out to young people he dealt with in court “set me on the path to trying to be something other than a courtroom prosecutor.”
He left the DA’s office in 2011 and spent a year teaching at Boston charter school. Henning said the contact with teenagers was rewarding – he’s still in touch with several former students — but he didn’t think teaching was his strong suit and he returned to the DA’s office in 2013.
Henning, seen by many as the front-runner in the race, has said that if elected he wants to launch a mentorship program that would pair prosecutors and police with at-risk young people to try to help steer them away from any involvement in the criminal justice system.
He rejects the idea that there anything inconsistent about reaching out to people he has also prosecuted in court. “Holding people accountable and helping them are not mutually exclusive,” he said. “And I think it actually does a disservice to people if you don’t do both.” People need to be held accountable for their actions, he said, especially crimes that involve weapons or violence. “But it doesn’t mean we give up on you.”
Shannon McAuliffe, a veteran defense lawyer and one of the other four candidates in Democratic primary for the DA’s post, said not giving up on people is the right approach. But she said it has to involve a wholesale shift in how the office deals with young offenders, not just offering a hand to those with troubled backgrounds who end up behind bars.
“Placing someone already traumatized into a hyper-traumatizing and violent place like jail makes them worse – worse for themselves and worse for the community,” said McAuliffe, who most recently ran the Boston office of Roca, a nonprofit that works with gang involved young men on education and employment issues. She said we can hold young offenders accountable in much more positive ways that make them less likely to commit crime again.
“Greg continues to do the same old, same old,” she said. “Prosecute, lock up – and then try to help them dig themselves out of a deeper hole.”
Paying attention to the issues that have led young people into the criminal justice system “needs to happen well before people serve their sentences and get out,” said Rachael Rollins, a former US assistant attorney and general counsel at the MBTA and Massport, who is also vying in the Democratic primary. “Greg has been part of this system that is very flawed.”
Henning says he dealt with cases as a prosecutor by considering all the factors involved, and that he would bring that same approach, not a one-size-fits-all policy, to cases as DA.
Henning is clearly benefiting from the backing he’s received from Conley and police officers, and he stands out as the establishment candidate in field where voters hungry for reform may divide their support among several other candidates. He balks at many of the changes other candidates support, such as eliminating most mandatory minimum sentences.
At the same time, he insists that he represents more than the status quo. Of his work with offenders that he prosecuted, Henning said there are others in the DA’s office “who think that what I do is crazy.” Along with setting up a mentoring program for at-risk young people, if elected he said wants to arrange for prosecutors in the office to meet with people who have been incarcerated and trauma experts “to teach them how our work impacts people.”
“All of these things are different than the way the office is run now,” he said. “Status quo means keeping it the same and not changing it.”