Working as a Jewish Chaplain at Rikers Island Correctional Facility comes with a unique set of challenges.  For instance, something as simple as sitting down to write this piece involved going through eight metal gates, waiting for an “inmate altercation” to clear and securing one of the few computers in the facility.  When I clicked on an old WexnerLEADS article for inspiration, I received the following message: “Content blocked by your organization – Reason: This Website is filtered by DOC policy: Traditional Religions.”  As an aside, while typing that sentence, an administrator working in the same office asked me, “You hear anything about that slashing that took place earlier?”  So like I said, unique.

As President John F. Kennedy noted more than half a century ago, the Chinese character for danger is the same as opportunity, and to say that opportunities for leadership and spiritual development abound at Rikers Island would be an understatement.  When I tell people I work at a jail, the first question is inevitably, “Do you feel safe there?” Personal safety does not even approach a top concern of mine. Rikers Island is the land of “we’re working on it,” “I’ll get back to you,” “somebody should really fix that” and countless other work avoidance techniques.  Nearly everything is a favor.  Beyond an inmate escape, very little else is considered an emergency. Without exercising leadership, Jewish services simply would not take place.

When I started my job, in order for my weekly services to take place, I needed to convince the Deputy Warden of Programs, Captains and Correction Officers that Jewish services were worth their time.  Rabbinical school taught me how to lead services; my Wexner training taught me how to ensure they took place.  I found a mentor in a veteran Jewish Prison Chaplain who helped me navigate the bureaucracy.  I demonstrated to the Director of Ministerial Services that I was reliable by volunteering for as much grunt work as possible. I sat down and got to know each of my coworkers and am still finding ways to show them they can rely on me. In short, I am building a reputation.  And as opposed to the private sector where an employee’s worth can be measured in terms of revenue brought in versus salary paid out, here, one’s reputation depends on being the needed ally to make things happen.

Eventually the Programs Department got on board and soon after, they brought inmates into the chapel for Jewish Prayer. I heard a voice inside: “Now, the real leadership begins.”  Each week, a stream of human beings are brought in, the detritus of society.  They all have a story of how they got here, some more closely guarded than others.  Many of them are institutionalized, believing their paths impossible to change.  When I ask an inmate in his early 20s who attended a very prominent Jewish day school what he does, he answers, “I am the criminal element.”  Jail is just part of their lives. The vast majority are in for petit larceny, burglary and assault: crimes committed to obtain money to buy drugs, the largest contributor to the Jewish inmate population.  Another young inmate struck and killed two people with his car.  He had never been in trouble with the law previously.   How to shepherd or minister to them?

I started work in January, and over these 8 months I have tried leading my flock away from drugs. I hear the sad refrain, “You’re right, Rabbi. I ain’t never coming back here. I’m done with heroin forever.” And yet, so many are released and re-offend. I reach out to their parents, grandparents, counselors, parole officers, rehab facilities, you name it. I lead unconventional services, demanding participation from inmates accustomed to thinking Jewish services means watching a movie about the Holocaust while drinking Kedem grape juice and eating matzah. We’re expecting about 50 for Rosh Hashana. Ironically, we have two inmates with strong Jewish education backgrounds who would be more than capable of leading services but refuse to travel on the bus from their facility to the one hosting services. Now the challenge is getting them a shofar, which is considered contraband (“a potential weapon”).

The Wexner lesson of not being afraid to fail as long as we examine our failures and learn from them is one I return to often. In German correctional philosophy, every inmate who re-offends is a failure, and I take that idea to heart.  Whenever somebody comes back, I ask myself if there was anything I could have done better to prevent it. I remember Marty Linsky telling our class that “enduring scars” are part of leadership. Each scar is a lesson that I hope to learn from so I can help counsel an inmate in the future away from drugs and crime and into a more fulfilling path.

Andrew Scheer, a Wexner Graduate Fellowship alum (Class 24), received ordination from Yeshivat Chovevei Torah. After earning his B.A. in Jewish History from New York University, Andrew worked for the New York Mets for three seasons and taught English in the Japanese countryside for a year, concurrently teaching Hebrew School at the JCC of Tokyo. While at YCT, Andrew had the privilege of serving as a rabbinic intern at Congregation Sherith Israel in Nashville, TN and Congregation Orach Chaim on Manhattan’s Upper East Side, and also traveling to Senegal with American Jewish World Service and participating in the Fellowship at Auschwitz for the Study of Professional Ethics. He also staffed a Birthright Trip consisting of participants from all of America’s service academies and ROTC students and since January, serves in the United States Army Reserve as a Chaplain Candidate and as the Jewish Chaplain for inmates incarcerated at the Anna M. Kross Center, the largest correctional facility on Rikers Island. He can be reached at