Professor Jeff Bolster’s book“Black Jacks: African American Seamen in the Age of Sail” and his years of mentoring helped convicted felon Gregory White pursue his lifelong dream of a life on the sea. With the help of Bolster and his brother, Peter, a mariner who gave White his first job on the water out of prison, White has turned his life around and is living his dream.
The heartwarming story of this long-time friendship is captured in the Washington Post’s recent article “‘Black Jacks’ persuaded inmate Gregory White to shape up and ship out.”
We asked Bolster to tell us more about his friendship with White and what it has been like watching him turn his life around.
What was your first reaction when Gregory contacted you and sought your advice?
That was a long time ago. I think that I tried to be encouraging and not judgmental. His letter came out of the blue. But after I responded, he wrote back to me. And so we developed a pen pal correspondence that allowed us to size the other up over a long period of time. We wrote for years before I ever heard his voice or saw a picture of him, much less met him in person.
Gregory White writes after that first contact with you, “It was almost as if he had heard me shuffling around in the dark and handed me a flashlight.” When did you realize how profound of an impact you made in this man’s life?
That realization grew, but it took a long time. There were many phases to this relationship. Greg was in prison for the first six years we corresponded. I was living in Denmark for a year, where I had a Fulbright Chair, when he was paroled. That was in October, and I did not return to the United States until the following August. But we continued to write, and we also finally talked on the phone.
What were some of the most challenging aspects of mentoring Gregory?
No challenges. He is a very sweet guy. He takes disappointments in stride, and there were lots of disappointments. Sometimes I think I was more disappointed at times than he was when he got turned down for something that I believed him eminently qualified to do. The rejections were because of his past, because of something stupid and illegal he had done years before.
What were some of the rewards of mentoring Gregory?
Lots of rewards. He was appreciative. He was responsive. He wanted to move ahead on the path he had charted. After a while I could tell he had determination. I was also happy to enlist my brother, Peter, who is mentioned in the article, and my old friend and shipmate, Capt. Daniel Moreland of the Barque Picton Castle, to mentor Gregory. They are both professional mariners.
How did your brother react when you proposed he hire Gregory?
By then he had heard about Greg so he took it in stride just fine. Peter has a fairly large staff, and he has responsibility for hiring and firing. Greg had to go through all the procedures at the Living Classroom Foundation. I certainly helped open the door for him, but after Peter interviewed the guy he was willing to give him a chance. And it worked out fine.
What has your relationship with Gregory taught you?
Personal relationships make a difference. Books make a difference. We all know that the recidivism rate for men who have spent decades in prison is very high. I am extraordinarily proud of Greg for meeting his parole obligations, and for not drinking or doing drugs or getting into any trouble since he has been out. He has beat the odds.
My relationship with Greg has also put a human face on the travesty of the American incarceration system. As the new book “The New Jim Crow: Mass Incarceration in the Age of Colorblindness” by Michelle Alexander refers to it, "mass incarceration" is the "new Jim Crow in the age of colorblindness." Our nation has more people in prison than some nations have people. What Greg did was by no means excusable, but we need to ask ourselves if putting him in prison for 22 years was good for him and good for us