Boston mayoral candidate Tito Jackson in his living room.
Boston mayoral candidate Tito Jackson in his living room.
John Tlumacki/Globe Staff

Jackson finds he is suited to public life

The origin story of mayoral candidate Tito Jackson.

Successful people often have compelling origin stories that say something about who they are, or how far they’ve come. Bill Clinton is from a place called Hope. Michael Jordan was left off his high school varsity basketball team. Marty Walsh survived cancer and addiction to build his public career.

It is not so easy to distill Tito H. Jackson’s origin story to one line. He revealed publicly in 2014 that he was born to a teenage rape victim. Adoptive parents raised him in Grove Hall, between Dorchester and Roxbury, with the Holy Bible and an iron hand, during some of the most violent years in the city’s history. His father was a community activist for worker and minority rights. His best friend died with a bullet hole in his heart. He has a gift for building relationships; people have long gravitated to him.

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“I’m the sum total,” Jackson said, “of all of the people who have spoke life into me.”


Voters in Roxbury and parts of Dorchester, the Fenway, and the South End have elected Jackson four times to the Boston City Council, after he fell short of winning a citywide seat in 2009. Usually dressed in a suit and hard to miss at 6-foot-2 and 265 pounds, Jackson is forgoing what looked to be an easy reelection to the council, choosing instead an underdog mayoral bid against the incumbent, Walsh.

If he wins, Jackson would become the first black mayor of Boston, a majority-minority city that has not had a black mayoral candidate on the November ballot since Mel King in 1983.

Jackson has made income inequality and the economic pressure on the middle class the pillars of his campaign, and has drawn on his personal backstory for the credibility to address those issues.

The 42-year-old councilor is at ease speaking on race and class, equally comfortable in City Hall’s corridors of power or shaking hands along the toughest streets of his district, where he has lived nearly all his life. As an undergrad at the University of New Hampshire, Jackson was elected student body president by a nearly all-white school. Even then, he moved easily among groups and cliques, neither alienating nor settling down with any one of them.

“Tito belonged to everyone,” said Shelly-Ann Richmond, a former college schoolmate of Jackson’s.


A framed photograph Tito Jackson as a child sat above a couch in the living room of the house where he grew up.
A framed photograph Tito Jackson as a child sat above a couch in the living room of the house where he grew up.
John Tlumacki/Globe Staff


In his district, it seems everybody who Jackson bumps into knows him, and has a story or a bit of news to share. Jackson will lean in to listen and to whisper. Most of these encounters break up with laughter. Jackson has good comic timing and a command of self-deprecating jokes. “UNH was transformative for me,” he likes to say. “I went in skinny.”

A friend described Jackson as somebody who knows at least a little bit about everything, so he can gab with just about anybody. His political style is to persuade by educating; he liberally cites statistics and facts. When Jackson gets going on a topic, he can slip into a preacher’s cadence. Conversations often circle back to faith.

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“My faith is such a large part of who I am because, hey — all the data says I’m not supposed to be here,” he said, in one of two lengthy Globe interviews for this profile. “In the ’90s when I was growing up, the mentality was that boys who looked like me didn’t live past 25.

“I’ve been blessed. My calling is to share blessings with others and ensure my life is faith in action. Faith is great, but there’s an African proverb: ‘When you pray, move your feet.’ It is so critical for me to step forward and not only say, but most importantly to do.


Politically, he is a progressive Democrat with the instincts of a community organizer, inherited from his late father, Herb, whose example over decades molded Jackson into an activist.

Herbert Jackson was born in Boston in 1939, and grew up a foster child in Plympton, a small town south of Boston. Herb Jackson liked helping people, and became a “real roll up your sleeves, get down in the weeds, grass-roots activist,” said Charles R. Stith, who was the Jacksons’ minister at Union Church and was later US ambassador to Tanzania. Herb Jackson worked with the South End church on voter drives in the mid-1970s, against the backdrop of school desegregation and court-ordered busing. The registration drives were meant to build a voter base capable of boosting candidates of color into office, Stith said.

The work paid off. In 1977, John D. O’Bryant was elected the first black member of the Boston School Committee. Four years later, Jean McGuire became the city’s first black school committeewoman. That same year, 1981, Bruce Bolling was the first African-American elected to City Council in a decade.

Herb Jackson, who died in 2002 at age 63, opened one of the city’s first black-owned cab companies and was an environmentalist who ran a recycling business. His evenings were busy with neighborhood meetings, to which he sometimes brought young Tito. He would rant about illegal dumping in Roxbury and was known to pick through trash looking for clues to who left it. He had a dedicated phone line in his house for community-related calls.

Herb followed former city councilor Chuck Turner as head of the Greater Roxbury Workers Association, policing construction sites to see if contractors were hiring the required number of local and minority workers, and protesting those who weren’t. Jackson made little money as a community organizer. Sometimes he got threats.

“Even when contractors were opposing him, they had to admire him for his persistence, the fact that he would always come back,” Turner said.

Herb Jackson’s activism was grounded in his command of facts and information, Turner said. “His organizing was designed to raise people’s consciousness about the need for taking action.”

At a young age, Tito began to emulate his father.

“He started looking like him, he started acting like him,” said Tito Jackson’s mother, Rosa. “Some things he would say to me, I’d say, ‘That’s your dad coming out of you.’ ”

Tito Jackson walked down the staircase from the second floor of his home.
Tito Jackson walked down the staircase from the second floor of his home.
John Tlumacki/Globe Staff


In the late 1960s, Herb Jackson met a young woman who had grown up in Greensboro, N.C., as Rosa Johnson. After high school, she had ridden a Trailways bus to Boston, thinking the city would be the best place to continue her education. She took a number of classes at Northeastern University and worked at Mass. General as a dietary aide. She was a young woman from the South, without much money, but wanted “to do more for myself,” Rosa, now 75, recalled.

When she met Herb, Rosa was recently widowed with three children. She was grieving, and he was kind to her. He cared for her as a friend. One day, Herb told Rosa’s mother that he planned to marry her daughter.

“She said to me, ‘I didn’t know you were going to get married to Herb,’ ” Rosa said in a phone interview from her home in Jacksonville, Fla. “And I’m looking at her in shock. I said, ‘Where’d you get this?’ I didn’t know either.”

Herb and Rosa married in 1970. Two years later, they bought a home on Schuyler Street, where Tito Jackson still lives. He is a bachelor. “I’m a hopeless romantic and I believe there is somebody out there for me,” Jackson said. “I’m also very committed to doing this work. It’s not conducive to dating.”

His parents papered their home’s interior walls with enormous floor-to-ceiling murals of outdoor scenes, a world away from city life: a palm tree beach, an English garden, a hardwood forest in autumn. Today, the house is a pack rat’s clutter of papers, books and boxes, family photos and figurines.

Herb and Rosa had four children between them from their previous marriages, what Rosa calls “a beginning of a family.” They both loved children — Herb had grown up with eight in his foster home — and they decided to adopt.

In 1975, they were offered a 2-month-old boy. A foster mom had called him Bill.

Campaign posters from Tito Jackson's Boston city council race were piled in a box on the front porch of his home.
Campaign posters from Tito Jackson's Boston city council race were piled in a box on the front porch of his home.
John Tlumacki/Globe Staff


Rosa wasn’t keen on calling him Bill. She chose “Tito” from a book of baby names. Short and simple, she thought, so when he got to school it would be easy for him to write his name. It did not occur to her there was already a very famous Tito Jackson.

“I wasn’t even thinking of the Jackson 5,” she said.

The Jacksons knew nothing of the baby’s biological mother, and Tito Jackson didn’t learn about his birth mother’s circumstances until he was in college, he said. A doctor had asked him to track down his family medical history; the adoption agency revealed to him that his mother was a 13-year-old girl who had been sexually assaulted by two men, Jackson said.

She would be in her mid-50s now. Jackson very much wants to find her. He supports legislation that would allow people like him to more easily locate their birth parents. He speaks of his birth mother in heroic terms.

“I see her as a strong, resilient, caring woman, who through a very traumatic experience did something I’m forever thankful for,” he said. “At that time it was not typical for children to have children. I’m eternally grateful.”

The circumstances of his birth also suggest his biological father was a rapist. Jackson doesn’t seem burdened by this. He recalled that when he got the news about his birth mother, he was in training at a sexual harassment and rape prevention program.

“It was a confirmation of my life,” Jackson said. “I was already doing the work . . . it was super confirmation I was doing the right thing.”


The Jacksons were strict parents. No baggy jeans. No swearing. No hanging out in the neighborhood. Young Tito signed up for all the activities he could, because he was not allowed to leave the house unless he had someplace to go. “I had to learn how to ride my bike in the driveway,” he said.

The rules, he came to realize, were “a matter of life and death.” In 1990, the year Tito turned 15, Boston logged a record 152 homicides, many not far from his home. He remembers breaking his 8 p.m. curfew once. When he got home his mother was in tears. She had thought he might be dead.

Jackson grew up a morning person, a news junkie, and an intense listener, his mother said. “In the morning he would get up while I’m trying to get [Tito’s siblings] ready for school,” Rosa Jackson said. “He’d be listening to the radio and he’s saying, ‘Mom did you hear this? They’re saying this, that.’ I’m saying, ‘OK, Tito, but you know we’ve got to move along.’ ”

His parents wanted to give him every edge to succeed, so they often sent him to school in a jacket and tie. “My friends would be like, ‘You know there’s no class picture today, right?’ ” Jackson recalled.

Jackson learned how to speak in public by reciting Bible passages before the congregation at church. He recalls one embarrassing service when he got the passages late, didn’t have time to practice, and stumbled over big words and long names. He felt down on himself, until a congregant kindly sought him out to say he did a great job — he just needed to work on his pronunciations. That little act of encouragement “just epitomizes to me the steadfast, persistent love in that community,” Jackson said.

Through the Metco program, Jackson went to Brookline schools, graduating in 1993 with a diverse class. He liked that the school staff had high expectations. It wasn’t a matter of whether he would go to college, but where.

Jackson’s first choice was Morehouse College in Atlanta, the historically black college Martin Luther King Jr. had attended, and where his buddy from the neighborhood, Oronde Khary Allie, had started a year earlier.

But Morehouse didn’t award him enough financial aid, he said, and Jackson was steered to the University of New Hampshire by a former Boston school administrator, Roger Beattie, who coordinated UNH’s minority recruitment. Jackson’s campus tour included the field house, where he saw a number of students of color.

“It seemed like a lot of them,” Jackson recalled. “In fact, that was all of them.”

Of the school’s 12,000 students, roughly 75 were black, he said.

Tito Jackson placed a hard hat on a shelf in his living room graced with photos of his mother, Rosa, and his uncle Claver.
Tito Jackson placed a hard hat on a shelf in his living room graced with photos of his mother, Rosa, and his uncle Claver.
John Tlumacki/Globe Staff


It was not long before Jackson became a campus activist pushing for a more diverse school. He was among a handful of students who revived the defunct Black Student Union, which put together a list of demands, including more recruitment of students of color beyond athletes. The students gathered signatures and presented them to the administration, which agreed to take steps to make the campus more racially diverse.

Jackson’s activism on such an overwhelmingly white campus worried his parents, who feared a potential backlash, Rosa Jackson said.

“Tito, being such a little activist as he was, he went there and did a lot of changing,” Rosa said. “And that’s when Herb and I were nervous, because we didn’t know what would happen.” They prayed for their son. “We gave it over to God’s hands, and he did it; he protected him.”

Jackson majored in history. College friends say he was charming and affable, and seemed to know everybody. One of Jackson’s former college roommates, Malik Aziz, tells a story about how he and Jackson were among a group of UNH students who drove to a conference at Yale. The group had stopped to eat at a food court of a random shopping mall in Connecticut when someone came up and asked a familiar face: “Are you Tito Jackson?”

“Everybody at the table just threw their hands up,” Aziz said. “Tito’s just known everywhere.”

But Jackson’s sophomore year at UNH took a dark turn, and became one of the most difficult years of his life.

In November 1994, Oronde Allie, Jackson’s buddy who had gone to Morehouse College, was carjacked and shot in the back after leaving the school library. Left bleeding on the curb, he died at an Atlanta hospital. Two years later, a 22-year-old preacher’s son was sentenced to 50 years in prison for Allie’s murder and other crimes.

Jackson was stunned by his friend’s death. Depressed, he skipped too many classes and came close to flunking out of school.

“It was difficult for me to deal,” he said. He took a semester off, and wound up working two jobs that would shape his sense of what he could do, and wanted to do, in his career.

Tito Jackson worked on a laptop on his dining room table.
Tito Jackson worked on a laptop on his dining room table.
John Tlumacki/Globe Staff


At one job, he fulfilled data requests at a bank being gobbled up in a merger. Longtime employees were terrified they would be laid off. They didn’t control their own destiny. It made Jackson want to get his degree all the more.

In his other job, at a Lechmere store, Jackson was hired to carry TVs to customers’ cars. He soon moved up. “I told my manager I was too good-looking to be in the warehouse,” Jackson said with a smile. He was moved to the retail floor, where he learned skills he would later use in his career in sales.

In 1997, back at UNH, Jackson ran for president of the student body and won with 55 percent of the vote in a three-way race.

“Twelve thousand kids on campus,” he recalled. “It wasn’t the black vote.”

He knocked on doors in the campaign. “Every single door in the school,” Jackson said. His platform was “student empowerment,” he said, the idea that “the school should be there to meet our needs.”

He was quick to speak out on racial issues at school and address episodes that he considered racist, said Aziz, his former schoolmate. “Tito was not willing to let anything slide,” he said. “We felt we had to speak to every incident.”

One time, Jackson and Aziz paid a visit to a student who had hung up a Confederate flag. Jackson took the lead in trying to persuade the student to take it down, Aziz said. “We let him know how offensive it was to people of color, in as soothing a voice as we had,” he said.

In that case, Jackson couldn’t make the sale. The student would not remove the flag.

“It went better than most would expect, but it was not what I wanted,” Jackson said. He recalls thinking, “This is my school; I’m not leaving. But what does it mean for the next person who comes along after me and sees that?”

In 1998, frustrated by what they considered the slow pace of change at UNH, Jackson, Aziz, and other members of the Black Student Union led a sit-in at the office of school president Joan Leitzel, demanding more be done to diversify the campus.

Aziz, then president of the Black Student Union, was initially reluctant to take such a drastic step, which put students at risk of punishment and arrests, he said. Jackson, though, “was all for it,” Aziz said.

For 16 hours, some 60 to 100 students – both white and students of color — occupied the office in silence while a few leaders, including Jackson, negotiated with administrators. “For hours on end we were sitting there, arguing our points,” Aziz said. Jackson had already built a rapport with administrators, and “it would not have been a success without Tito at the table.”

Under an agreement struck that day — a victory for the students — administrators agreed to steps to increase the number of black students and professors. In 2013, marking the 15th anniversary of the sit-in, Jackson returned to campus for a panel with other leaders of the demonstration. News coverage of the reunion noted that the climate for minority students had improved, but that UNH had still not yet hit the target numbers set in 1998 for black students and faculty.

Tito Jackson's home on Schuyler Street is the house he grew up in.
Tito Jackson's home on Schuyler Street is the house he grew up in.
John Tlumacki/Globe Staff


After college, Jackson worked as a pharmaceutical sales rep, marketing drugs to physicians. At one job, with Eli Lilly, he sold the erectile dysfunction drug Cialis. He loved selling Cialis. “It was a really fun product to market, but also it helped a lot of people and helped a lot of relationships,” he recalled. “I felt very encouraged and motivated.”

While working for Alpharma in 2005-06, he marketed the pain reliever Kadian. Jackson, who has made the opioid crisis a key issue in his campaign, came under scrutiny last spring for marketing the morphine-based drug to doctors. He defends his work, saying Kadian helped patients in chronic pain, often in palliative care.

“All of the medicines I sold, at the time I considered them to be things that helped patients,” he said.

Alpharma fired Jackson in 2006, saying that he failed to meet company standards for administrative work, including his expenses, the Globe has reported. Jackson sued Alpharma in 2007, claiming unpaid wages. The suit was ultimately dismissed. Jackson says he harbors no bitterness about his time with the company.

“The thing about being in the private sector, sometimes you get laid off, sometimes you get downsized, and sometimes you get fired,” he said. “That’s a reality. I’m not ashamed. Things happen, you move on.”

In 2007, Jackson joined the state’s Office of Business Development, where he worked to recruit and retain technology businesses, and help them expand. He liked the work. He liked working for then-Governor Deval Patrick, whom he found inspiring. It felt like he was helping people.

“Seeing what happens when you bring opportunities and jobs, getting to look in people’s faces who got an opportunity based on some of the work that you did — that was motivating.”

Patrick, he said, “told us we got the government we deserve. He told us to run.” To run for office. “I heard him and I listened.”

Jackson had previously been involved in nonpartisan politics, working on a voter registration project. The first political campaign he worked on was Patrick’s, he said.

In 2009, Jackson began mulling a run for City Council. He prayed for guidance. Not long after, a 15-year-old, Soheil Turner, was slain at 7 a.m., at the corner of Adams and Dudley streets, not far from Jackson’s home. Turner had been eating a honey bun and waiting for a bus when he was shot in the back of the head.

Jackson never knew Turner but said he was deeply affected by the murder. Eight years later, he still speaks haltingly when he talks about it.

“We undervalue the whole city of Boston if we undervalue the lives of anyone in Boston,” he said. “We lose a bit of the future if any young person leaves us.”

“I knew that I had to get off my butt and get out here and run,” Jackson said. “And run even when people said I didn’t have the name or the money.

“I knew I had a very important perspective to bring,” he said. “And a story to tell.”