Against that backdrop, Lisante is working to restore hope. He said the worst part of his job is seeing teenagers who seem to have given up, but the best part is watching those same young adults turn a corner. We met Lisante at a conference for “transition specialists,” who help students regain their footing after they leave detention centers. It’s one way he’s trying to make sure these students get a second chance, he said.

“When I first went to Rikers, I had a whole different picture,” Lisante said. But once he was there, he remembers thinking, “This is it? These are the most egregious kids in New York City? I just realized they were a lot like my own sons.”

We spoke to Lisante about his work in District 79, how he plans to help New York City’s court-involved youth, and whether New York state’s graduation requirements are too tough. The interview below has been condensed and edited for clarity.

Monica Disare: What got you interested in this type of work?

Tim Lisante: I worked in a vocational high school in the South Bronx and I became assistant principal of special ed there. One day, I saw this ad and all it said was “assistant principal, Rikers.” … So I went to Rikers, and the funny thing is, I never went to Rikers before I took the job. I interviewed in Manhattan and I remember driving over the bridge and seeing all these jails and that razor wire and saying maybe I should turn around. But that was 30 years ago.

When I got to Rikers, I really found that was my niche because the students [have] so many needs, multiple needs. … It’s really exciting work and it’s a population that really gets overlooked, that has no real advocates.

Disare: You said you grew up about five miles away.

Lisante: I went to Holy Cross, a Catholic school in Flushing, [Queens]. Literally, it’s less than five miles from Rikers, but my experience was so great in high school. That’s one of the reasons I became a teacher. I love school.

So then when I go to Rikers … and I see the experience that 16- and 17-year-olds have, it’s so different from what it should be. The worst experience of my career is seeing kids who give up hope at 16 and 17. What we’re trying to do is renew that hope.

There’s nothing that we like better—that I like better—than these graduations in June. One of the best things about the graduations is looking at the parents. These parents have been through a lot. They come, like, two hours before the ceremony. They’re so happy. They don’t want to leave after it’s over. Everybody’s taking pictures and everything because their children have come a long way. Those graduations … make this work really worthwhile.

Disare: How do you tackle the hopelessness?

Lisante: One of the things that we are really proud of in District 79 is we have a very good counselor-to-student ratio. We have social workers, guidance counselors, that are really, really dedicated and we give them training. I’m also concerned about them because they’re hearing horrible stories every single day, you know, in small groups and in individual counseling.