Daniel Zhao

In the 1980s, William “Juneboy” Outlaw III was sentenced to prison for 85 years for co-running one of the largest drug gangs in New Haven — “The Jungle Boys”.

Now, Outlaw is a community outreach worker working to help at-risk youths in New Haven and the subject of a recent biography.

On Wednesday evening, about 50 community members gathered at the Yale Bookstore to hear excerpts from “Citizen Outlaw” — a biography by Charles Barber chronicling Outlaw’s journey from criminal to activist. Barber is a writer-in-residence at Wesleyan University and a psychiatry lecturer at Yale. His work in criminal justice research led him to Outlaw, and the two spent five years working on the book.

“I had to do what I had to do to survive [in prison],” Outlaw said to the crowd on Wednesday evening, after initially being unable to speak for a few minutes, overcome with emotion. “Nobody in this room will understand that. That’s untreated trauma that I live with every day.”

In 1989, Outlaw was sentenced to 60 years in prison for the 1988 death of Sterling Williams. Prosecutors claimed he had killed Williams in a drug-related dispute. Outlaw was sentenced to an additional 25 years for second-degree assault, and his time in jail proved to be tumultuous. He became a “shot caller” — a prison gang leader — wielding power over 150 men and was transferred to maximum-security federal prisons across the country.

However, an appeal from his attorney sliced 60 years from Outlaw’s sentence. Upon his release, Outlaw moved to a halfway house and found himself working at Dunkin’ Donuts in New Haven. He struggled with his trauma in the following days, resulting in insomnia and hallucinations that were similar to the effects of psychedelic drugs.

Outlaw described an assessment he was given upon leaving prison, based on his crimes and his behavior while incarcerated. This assessment predicted that in a year, Outlaw would end up dead or reincarcerated. In his book, Barber cites that 65 percent of released black men are killed, and the same proportion of white men end up overdosing on drugs.

“But I knew in my mind I wasn’t going back to jail,” Outlaw said of the report. “I knew I wasn’t going to hurt another human being.”

Instead, Outlaw began working with the Street Outreach Workers shortly after leaving Dunkin’ Donuts. The Street Outreach Workers work to mentor youths from age 13 to 21 in New Haven involved in risky activity, such as gang violence, drugs, shootings, fighting and truancy. Mentors connect with youths from social media or from referrals from law enforcement and schools.

Often, the outreach workers get tipped off from people on the streets to come on the scene and defuse tense situations. The program has expanded over the years to work in tandem with law enforcement, the school system and Yale New Haven Hospital.

“When someone gets shot, we go down to the emergency room,” Leonard Jahad, executive director of the Street Outreach Workers, told the News. “We calm everyone down, so that their boys don’t retaliate. Then we start working with the victim. Either they’re going to retaliate or they’re going to change their lives.”

The Street Outreach Workers saw one of its biggest successes when Outlaw, alongside fellow outreach leader Trent Butler, brokered a truce between two of the largest rival gangs in New Haven. Clashes between the gangs from Read Street and Derby Avenue neighborhoods had resulted in spats of gun violence but eventually decreased as a result of the truce.

“He talked about how he wanted to be a redeemer, how he wanted to clean up the streets he had at one time destroyed,” Jahad said, referring to his first meeting with Outlaw. “He immediately got my respect. He’s so passionate and patient with the young men and women he works with.”

However, at the event on Wednesday, Outlaw acknowledged the pain he had caused the victims of his crimes.

He cited deep remorse, stating that he would never forget those he had hurt.

“My reason for getting my story published was to tell my story,” Outlaw told the News. “The most important part of the book in my redemption story.”

Citizen Outlaw was published in October 2019 and is available at the Yale Bookstore.

Meera Shoaib | meera.shoaib@yale.edu