Most Likely to Succeed: Greg Walton

Greg Walton never had a shot. His mother was an addict, he didn’t know his father. He was bounced into foster care and became easy prey for outside influences. So why is he now an award-winning IT specialist at MIT, and the first alumnus to sit on Year Up’s Board of Directors?

By Craig Antolini

Greg Walton was 19 and could downright fly. A former outfielder, he still measures speed in base-hits denied, and at that time he says he could chase down any would-be triple driven his way. He had proven he could outrun just about anything.

He had outrun every disadvantage laid in front of him. He had outrun a mother who had left him in favor of a drug habit, and a father whom he had never known. He was the first of his five siblings to outrun the dysfunction that was supposed to overtake him.

So after outrunning all that, he knew a cop had no chance—not when he was running with purpose. “I’m running because I’m scared,” he says. “You’re not going to catch me.”

Yet how it played out, Walton found that the one thing he couldn’t outrun was his own desire to be caught.

He had been a star, sociable and charismatic, a stud athlete who owned space on school honor rolls, hosted dance parties and led recruits on tours of his college campus. Now here he was acting as a wingman for some guy who had a Lincoln Navigator and flashy rims and had persuaded Walton to quit school because there was something better for both of them in Florida. That had fizzled and he was back in Boston, hiding in an alley with an unloaded gun in his pocket.

When the police flushed him out with a flashlight, he was relieved. He says some kind of force intervened. “Call it God,” he says. “This is enough, you’re done. I’m stopping you. It’s over.”

As the cops led him away, Walton could not stop confessing, to much more than they accused him of. He was confessing to a misdirected life.

“I kept saying, ‘I’m not a bad guy. This wasn’t supposed to happen to me. My older brother did this life. My mother did this life. This wasn’t for me. I was on a different path. I’m not that guy.’”

The Bones Are the Best Part

No, he wasn’t that guy. Years later, Timothy Dibble could see that too. When he asked Walton to be the first Year Up graduate to join the organization’s Board of Directors, Dibble, then the board chairman, told him, “The only difference between you and me is you got caught.”

It was a meaningful remark, implying the role of circumstances and surroundings, and luck, all the things that put Walton on a course meant to deposit him in a place far different from the one he now occupies. His life has been a case study in nature vs. nurture; his accomplishments defy his upbringing. He was gifted but by no means blessed.

“Conceived in Boston, born in North Carolina,” Walton says.

While pregnant with him, his mother left town with another guy, so he never knew, or even knew of, his father. Her drug addiction led to him and his siblings getting shifted into foster care when he was 4.

But Walton had a knack for finding the right people—or for having them find him. His great-grandparents lifted him out of foster care when he was 6, returning him to Boston, and taught him about selflessness and responsibility, by way of such undesirable tasks as cutting his great-grandfather’s toenails and helping him use a urinal. He also learned never to leave an uncleaned plate.

“We’d eat chicken wings and he’s yelling at you for not eating the bones,” Walton says. ‘You wastin’ this! That’s the best part!’”

When his great-grandfather passed, an aunt and uncle in a big house in Dorchester took him in. The uncle became Walton’s replacement father figure, a hard worker who commanded the household, while showing Walton there was more to manhood than that.

“He would find ways to show you that he cared about you. It’s 4 in the morning on the weekend and he’d kick in the door and be like, ‘Whoever gets dressed first is going fishing.’ And we’d go fishing. He was the only person I’d ever gone fishing with.”

When he most needed someone, there was the high school guidance counselor who took an interest in him and kept him on the path to graduate, and then resurfaced as he sat in prison, serving a year for illegal firearm possession.

She sent him letters, assuring him he would be OK. “This is just a speed bump,” she wrote. “You’re going to be great. I know it. I’m not giving up on you.”

When Walton got out, she told him about Year Up and implored him to apply. He was skeptical. “They’re not going to charge you, but you’re supposed to be getting all these things—an internship, a stipend, all of this stuff,” he says. “It didn’t make sense.”

But he applied, and to his astonishment was accepted. Walton entered the program in January 2006, five months after getting out of jail, still expecting to find out it wasn’t on the level. He came around in the first week, when he met Year Up founder and CEO Gerald Chertavian, who took note of Walton’s big personality.

“He pulled me to the side and said, ‘You’re either going to be a leader of this class negatively or positively,” Walton says, “but you’re going to be the person who decides that.’”

At a Board meeting, Gerald Chertavian presents Greg Walton with Year Up’s core value award, “Build Trust & Be Honest”.

Appreciative, he sent Chertavian an email and thanked him for the conversation. “The dude replied in less than a couple of hours,” Walton says. That left a mark.

“It was from that point that I took Year Up seriously. If the CEO himself is replying to me, then this dude’s legit. So whatever they asked me to do, I was in. I was all the way in.”

Walton flourished on Year Up’s IT track. He knew his way around technology. In high school, he was a noted mixmaster, making CDs for his friends and teachers: $8 for a custom CD, $5 for his own blend.

“If people wanted the best of Barry White, I was making the best of Barry White,” he says.

He was on his computer constantly, so he grew adept at troubleshooting and learned about software and a computer’s internal processes. “I didn’t know everything, but I was pretty proficient.”

After graduating Year Up at the top of his class, Walton was bouncing between temp jobs when he got a call from the Massachusetts Institute of Technology (MIT), which needed someone in its Information Systems and Technology department. He took the job in June 2007, and within weeks was moved from the front desk to the support team, providing tech help to multiple campus departments.

At 33, he is now in his 11th year at MIT. In 2017, he won an Excellence Award for client service, a statement about his people skills as much as his acumen. It’s the highest honor an MIT staff member can achieve. He was the first person from IT to win the award in 14 years.

Choices and Consequences

All the while Walton has maintained a close relationship with Year Up. In a demonstration of how things come back around, as a board member Walton now contributes to the performance review of the same CEO who cautioned him that he could use his abilities for good or ill. He chose good all those years ago and now tours the country speaking to young adults about the cost of choices, narrating his own path from jail to Year Up, and on to MIT. In July, in Boston, he became the first alumnus to deliver the keynote address at a Year Up graduation ceremony, and he’s been asked to do the same at Year Up’s upcoming national leadership summit in New York.

“It’s not that Year Up changed me,” Walton says. “It was always me. It was about helping me find myself and my purpose and helping me build the confidence to be who I was going to be.”

He looks back at his prison stint with gratitude, calling it “the most positive experience of my life. It reminded me that I did not want to be a bum. No matter what it took for me to make it happen, I was not going to be a bum.”

Alicia and Greg Walton with their children.

Plus, it also reacquainted him with a girl he knew in high school. He reached out to her while he was in jail and they began to communicate. Upon his release she was waiting for him at the exit gates. He and Alicia Walton have been married nine years now and have two kids.

He buttoned up another part of his personal life as well. About five years ago, Walton acted on an impulse to go track down his father. He was directed to the house of the man’s mother—meaning, Walton’s grandmother, whom he had also never met. The address panned out, and a 33-year absence ended in a half-day’s pursuit. When his father appeared at the front door, there was little emotion. It wasn’t a reconciliation, it was an introduction.

“It was like, it’s nice to finally know who you are,” Walton says. “There was still this unknown because it wasn’t 100 percent.” The relationship was cinched later when the DNA test came through. The two men now talk daily.

Walton is about to begin a Senior Education Leadership Fellowship program at New York University. He hopes to take what he learns from it and eventually design a Life Skills curriculum in the schools, to help prepare students for all the tasks and demands of adulthood.

“There’s more of me,” he says, referencing the millions of disengaged and demoralized young adults. “Because you got caught up with law enforcement doesn’t mean you’ll never be successful and gain a good job. Even if your parents never owned their own home, you can do that. It doesn’t mean it has to be the end. My story will carry me and will be something I share for years to come, to give them a sense of what is possible.”


Year Up Greater Boston, Class of January 2007 Currently an IT Support Engineer at MIT