"What happened to a lot of the other kids that were on the streets with you?" Logan asked.
"Well, unfortunately, you know, a lot of friends are either dead or in jail," he replied.
Wahlberg used to sneak out of his bedroom window and hit the streets for late nights of boozing, brawling, dealing and stealing.
Asked if he was a good thief, Wahlberg told Logan "I was pretty good. I was pretty good. I was pretty daring."
"You were a pain in the neck but you were always respectful," Father Jim Flavin told Wahlberg.
A rare positive influence for Wahlberg was Flavin. The street punk and the parish priest struck up an unlikely friendship. Flavin saw a glimmer of Wahlberg's future one day during one of Wahlberg's many appearances in court before a judge.
"He was just pouring it onto the judge, you know, 'I'll never do it again.' You know, 'I'm sorry,' and he was wonderful. You know, he started tearing up, and the judge just melted and said, 'All right, you know, this'll be it.' And he turned around and started out. And he looked at me and winked. And I said, 'You little bugger. That was an Academy Award performance in the court room,'" Fr. Flavin remembered.
"Father Flavin says that he could barely see you over the steering wheel when you were driving around, waving at him from stolen cars," Logan told Wahlberg.
"That is true," Wahlberg replied, laughing. "I just liked to drive."
"A lotta people like to drive cars, but they don't necessarily steal them to drive them," Logan remarked.
"Well, that was not a good idea," Wahlberg acknowledged.
But on an April night in 1988, Mark's crimes turned more serious. He attacked a man with a stick on a Dorchester sidewalk simply because he wanted the man's two cases of beer.
"Did you realize that this man who you'd hit with a stick in the eye, that he'd lost his eye?" Logan asked.
"Not until later, until we started going through the court proceedings," Wahlberg said.
Asked what he thought, Wahlberg said, "Oh God, I was just, you know, horrified."
Wahlberg said he apologized to the man. "I got up in front of the court, was able to address the court and him. And, then you know, they just put the shackles on me and took me away," he remembered.
Wahlberg pled guilty and was sent to a 19th century prison. He was 17 years old.
"It was one of the worst prisons we had in Boston," Flavin remembered.
Asked if Wahlberg was afraid, Flavin said, "He'd never admit it."
"But you thought he was?" Logan asked.
"Yeah," Flavin replied.
"At first, I'm thinking, well, I'm one of the guys now. I made it. And then I just realized, well, this is what it means to be one of the guys. And I just wanted more out of my life," Wahlberg said.