Three men mowed the lawn and swept trimmings outside Tito Jackson’s home in Dorchester on a recent Tuesday evening as a few campaign workers and volunteers set up tables and yard signs in the backyard.

The campaign event, a casual mix of door knocking voters in the neighborhood and a backyard barbecue, was hosted by the former Boston city councilor — but he was nowhere to be seen as a few folks started to arrive at quarter to five.

This time last year he was campaigning for mayor, going to parties like these for his own race. Now, he’s campaigning for Rachael Rollins, a candidate for Suffolk District Attorney.

Rollins arrived fifteen minutes before the host, driving herself, and wearing a dress, black blazer, and sturdy heels you can actually run for office in. “This is by far the coolest thing I’ve ever done in my life,” Rollins said.

Jackson rolled into the small party with a red backpack slung over his shoulder. He put his bag down and introduced Rollins to the group of less that a dozen campaign volunteers and guests standing in a circle in his driveway.

“I know that Rachael will have transformative policy that will ensure that we stop that school-to-prison pipeline, that we deal with the issue in the Boston Police Department where we only catch 4 percent — they call it a ‘solve rate’ — for non-fatal shooting, so we have neighborhoods and communities where those who have been victimized are seeing the perpetrators on a regular basis,” Jackson said, echoing much of the rhetoric he used in his own campaigns.

Jackson also referenced “the revolving door” of addiction, an issue he's working on now as the CEO of Verdant Medical, a medical marijuana group.

“We spend about $60,000 a year incarcerating folks, ironically — I was the chair of education [on the Boston City Council] — they spent $20,000 a year educating people in the Boston Public Schools,” Jackson said, taking a line from his campaign stump speech that he had delivered with some variation dozens of times last year when he ran for mayor against Marty Walsh.

The group dispersed with campaign literature to hand out to prospective voters in the hope of convincing them to support Rollins in two weeks. Jackson stayed behind to fire up the grill for a post-canvassing cook out. He had taken off his suit jacket, but still wore a white shirt and tie as he hauled two bags of charcoal out of the garage and over his shoulder. He fought to light the grill for a few more moments before sitting down on his back stairs for an interview.

Jackson’s orange and white cat, also named Jackson, trotted down the stairs and stretched as his owner scratched behind his ears.

Tito Jackson's cat Jackson.
Maddie Kilgannon WGBH News

But despite the politicking Jackson can’t seem to shake, he says that he’s not looking to get his name back on the ballot anytime soon.

Verdant is in the process of opening three dispensaries in Provincetown, Mattapan, and Rowley. Jackson sees his new role as an opportunity to continue the work he was doing at City Hall.

“We’re working to ensure that the cannabis base is as diverse as the usership,” Jackson said.

Employees at Verdant make at minimum $15 an hour, something Jackson fought for as a councilor and as a candidate. The cannabis industry is an opportunity to build wealth for minority business owners, Jackson said.

From 2011 until the end of 2017 Jackson was the District 7 city councilor representing Roxbury, parts of the South End, Dorchester and Fenway. During his tenure, Jackson repeatedly pitted himself against Walsh when it came to education funding — arguing that the Boston Public School system was severely underfunded. He also voted in 2014 to raise the city councilors’ salary by $20,000, a move he was heavily criticized for despite his rationale that the increase would result in higher quality candidates running for office.

After leaving the city council, Jackson took a temporary position at Parenting Journey as a fellow, working to lift families out of poverty. He began working at Verdant in May.

“I came from the medical sales business, and there’s just as much innovation in this space as we’re seeing in the pharmaceutical business,” Jackson said. “I believe that we’re on the vanguard of innovation and opportunity.”

When asked if he regretted leaving his council seat and launching a campaign for mayor, Jackson did not hesitate for even a moment before saying, “No. Not at all. Not a bit. Never. Not a drop.”

Jackson has not endorsed in the Secretary of the Commonwealth race or the Massachusetts 7th Congressional District race — both with candidates who were his colleagues in City Hall. When Jackson ran for mayor, he did not receive a single endorsement from his colleagues on the council, though he says that's not the reason why he hasn't formally backed anyone.

Even though he’s not where he’d hoped to be a year ago, Jackson says he's having the time of his life working at Verdant.

“Government people talk about limitations and what they can’t do," he said. "In business, people envision, talk about, and find solutions about what we can do."

Jackson then went back to working on the grill while Jackson the cat sat in the driveway waiting for the campaign volunteers to return for the cookout.