How mentoring changed a young man teetering between 2nd chance and jail

On a hot summer morning, Tanisha Freeman sits in the front row at the Bruce C. Bolling Municipal Building in the Roxbury neighborhood of Boston, dabbing tears from under her glasses. As she listens to her 21-year-old son, Taquari Milton, tell the audience how he turned his life around, she knows things almost turned out very differently.

Ms. Freeman, a Boston public school teacher and single mom, had long had her son’s future mapped out – he would excel in school before leaving for Morehouse College, a historically black school in Atlanta. From there, she felt, he could write his own ticket.

But halfway through high school, her studious child started “hanging out with the wrong crowd,” she says – to the point that he became embroiled in two, years-long legal cases, requiring numerous appearances in court. He washed out of two high schools and lost a job. His family was kicked out of their home after his landlord learned of his legal troubles. Mr. Milton’s life was teetering between a second chance and incarceration.

“At the time I thought that was the end of the road, that I would just be another black boy from America,” Milton tells the crowd at an event marking two years since Boston Mayor Martin Walsh began championing President Obama’s nationwide mentoring initiative, My Brother’s Keeper (MBK). “After my second [court] case threatened my mother’s job and my family’s livelihood again, I knew it was time to grow up.”

But neither Milton nor his mother knew where to turn until a chance encounter suggested that his desire for redemption could become reality.

'I need help ... I need a mentor'

Boston is home to more than 55,000 young black and Latino males – about half of the city’s male population under age 25, and 67 percent of all the city’s males age 17 and under, according to a new report by Root Cause, a consulting firm. Like many cities across the country, its social and economic future hinges in large part on helping a growing population of young men like Milton to stay on a productive track and prosper, researchers say, noting that by 2030, the majority of young American workers will be people of color.

Yet even as Boston is credited with substantial efforts to boost the prospects of young boys and men of color – ages 14 to 24 – the report’s authors say progress has stagnated on important measures like meeting math and reading standards and graduating from high school actually ready for college or work.

Milton was failing on both those fronts when he bumped into Conan Harris, a long-time family friend who now heads the MBK initiative in Boston.

“It was just kind of like this desperate plea: ‘I need work, I need help, I need a mentor,’ ” Freeman says.

To Freeman’s delight, Mr. Harris responded. “Conan just started with him – they took baby steps – they went places, they traveled, they would have lunch together … it’s been nothing but greatness since then,” she says with pride.

But for many boys and young men of color, that kind of connection – let alone greatness – remains elusive. Ultimately, Milton says, he decided on his own to change his life – but Harris was an invaluable guide.

Over the past 10 years, federal, state, and local governments, along with a handful of Boston philanthropists, have tipped more than $14 billion into organizations that directly or indirectly affect the lives of Boston’s black and Latino youths. These cover a spectrum of needs, including academic support, career exposure, mental health, life skills, and mentoring.

Still, minority academic achievement lags sharply, according to the Root Cause report. By eighth grade, just 10 percent of black boys and 14 percent of Latino boys are meeting or exceeding the reading levels expected of them, compared with 45 percent of their white peers. The gap is worse for eighth-grade math, with around a quarter of black and Latino boys achieving at grade level or beyond, compared with 65 percent of whites.

And when it comes to college, around a quarter of blacks and 16 percent of Latinos have associate’s degrees or higher, compared with two-thirds of whites, reducing their earning power in almost every case.

These deficits stem in part from a “structural racism,” says Andrew Wolk, founder and CEO of Root Cause and a co-author of the report, that puts up invisible barriers. Black students are 3-1/2 times more likely to be suspended or expelled for the same offense committed by a white student, for example. When it comes to job applications, white candidates are 50 percent more likely to get a callback than their black counterparts and 19 percent more likely than Latino applicants with “ethnic-sounding” names.

Resource rich and impact poor

The long-term economic impact is likely to be significant: “If we don’t treat [blacks and Latinos] as a potential workforce, then they become something else, they become people, individuals, families that may not have the wherewithal, the economic skills to move towards economic health or self-sufficiency,” says James Jennings, professor emeritus at Tufts University and a co-author.

But while Root Cause mapped 142 Boston organizations working to overcome these barriers, Boston faces a not-uncommon problem, according to Wolk: It’s “resource rich and impact poor.”

At its two-year anniversary, MBK, which operates in 250 communities nationwide, is trying to break that pattern targeting issues from academic achievement to job training to street violence. This year, the MBK School Success Mentor Initiative will pair 250,000 sixth- and ninth-graders with trained mentors. In Philadelphia, community leaders who pledged to cut in-school arrests by 50 percent have exceeded that goal.

Wanted: 50 mentors

In Boston, Walsh is only 50 mentors shy of his goal of 1,000 for the year. The city’s program is modestly funded at $100,000, but small, targeted grants can make a big difference, says Orlando Watkins, vice president of operations at The Boston Foundation, which is fronting half of the money.

Much of that money is for grants to individual “unsung” community leaders like John Borders, Mr. Watkins says. Mr. Borders runs a monthly breakfast program called Breakfast IV Brothers, which brings boys and men of color together to talk. Root Cause noted that the boys and men it surveyed felt such small grassroots organizations were particularly helpful, making it easier to foster real connection.

Freeman, Milton’s mom, says the kind of mentoring and advocacy Harris provided her son was a “necessity” in helping him navigate his way out of trouble. Now, Milton is into his second year at Boston’s Bunker Hill Community College, studying community organizing, and interning with the Violence Intervention and Prevention division of the Boston Health Commission.

'Everything counts'

“It’s no secret that the majority of our brown and black babies live in single-parent homes, and so they don’t have that sort of positive role model or mentor to kind of help them navigate what to do, and so programs like this are essential,” she says.

Growing up, Milton, who is now 21, says the “old g’s” (the neighborhood’s young men) would hang around the Dorchester streets where he lives smoking weed, getting drunk, and playing basketball. But they would also hand out small amounts of money to help the younger kids on the corner. That money was coming from criminal activities, enticing the younger kids to follow the same path.

Milton was one of those young men. Today, he still hands out a dollar here or there, but it’s coming from money he earns in his internship. To Milton, just his well-dressed presence in the community is a strong example for the neighborhood’s kids.

“Back then nothing really mattered because it was like, ‘if I don’t matter to people, why should everybody else matter?’" Milton says. "But now it’s like everything fits and everything matters and everything counts.”