Damian Jackson weighed two pounds when he was born. The doctors told his mother, Veronica Worley, that he’d have to stay in the hospital for 90 days, inside a tiny incubator, until his body was ready to fend for itself in the world. So each day, for 90 days, Worley went to visit her son. She’d put her hand inside the incubator to feel his impossibly small stomach, his little baby head, and his doll-size hands. But she wasn’t allowed to hold him. She missed him, even though she didn’t know him yet.

On the 90th day, Worley finally brought him home. Even then, he was only five pounds and she remembers her own mother scolding her for cradling him in the palm of her hand. “He wouldn’t fit in my arms,” Worley laughed. “He would have fallen out.”

Worley believes that her son’s premature birth set his course in life. He was always slightly undersized. That’s what got him into trouble, got him sent jail at age 12. She said he was carrying around a box cutter in the park after curfew. “Trying to prove he wasn’t a little kid, that he was a man,” Worley said. Later he joined the TBO gang—True Bosses Only aka Team Bang Out—based in Brooklyn. Jackson is 20 now, and he’s been at New York City’s Rikers Island jail for more than two years, awaiting sentencing on two counts of robbery, one count of assault, and two counts of attempted assault. Most of the charges are gang-related.

During his time at Rikers, Jackson said he’s spent a total of more than 200 days in solitary confinement. Almost every time he has been sentenced to solitary, his mother said, it’s been for a stint of 90 days. “That number alone just makes it crazy,” Worley told me.

On top of all the solitary time, Jackson has been forced to pay a $25 fine each time he’s been put in the box. That’s in addition to the thousands in fines Worley said he’s racked up from rule violations where he wasn’t sent solitary, restitution fees for property he’s damaged, and court fees.