Jeffrey Abramowitz: From the Courtroom to Community Empowerment

From Philadelphia Courtroom to Federal Prison

Jeffrey Abramowitz had what most people would call the American dream. For over 20 years, he practiced as a trial attorney at the same firm in Philadelphia. He had cars, homes, a beautiful daughter, and was married to a wonderful wife. But something was missing.

“I had what everyone would think is a dream. You know, you just you just are happy, married to go on vacations. You travel the world and you do all those wonderful things. But the truth was I really wasn’t happy,” Jeff told me. “I didn’t really have that drive and purpose that I have now that I was searching for and even as a lawyer.”

The choices Jeff made while searching for that purpose landed him in federal court in March 2012. When the judge’s gavel struck wood and he received a five-year sentence, something unexpected happened. “I was had this incredible sense of relief,” he said. Instead of going home to prepare for prison, Jeff was immediately remanded. He went straight from the courtroom through underground tunnels to the federal prison in Philadelphia.

Learning Behind the Walls

Jeff’s first cellmate was serving a double life sentence. The first morning, when the cells opened for breakfast, a line of men waited outside with their legal materials. Word had gotten out that there was now a lawyer in the unit.

“My cellmate took me under his wing and showed me, you know, what I needed to know. And yeah, the camaraderie inside of a prison is something pretty remarkable,” Jeff explained. He found sneakers on his bed, sweatshirts from other inmates, and people constantly giving him books.

Jeff threw himself into learning everything he could. He read over a thousand books during his sentence. He taught 65 classes. He practiced every religion available in the prison, from Muslim prayers to Christian Protestant services. “I really wanted to understand the world. And this allowed me to see the humanity inside our prisons and jails that I would never have gotten to see.”

He also learned practical skills. Jeff learned how to change oil on a car, operate a forklift, and oversaw the unicorn project at his prison. He lost 55 pounds and got in the best shape of his life.

From Prison to a Homeless Shelter

When Jeff got out, he faced a harsh reality. As a 50-year-old lawyer who could no longer practice, with a felony conviction and financial crime on his record, he didn’t even know if he could get a bank account. He had gotten divorced while incarcerated and had no home to return to.

Jeff made a decision that surprised many people. Despite having family he could have stayed with, he chose to figure things out on his own. “I’m just a proud person. And I dug this hole for myself,” he said. “I opened the door by doing something and making a choice that was wrong. And anything that flowed from that I took as I needed to learn from it.”

He ended up in a homeless shelter in North Philadelphia. The conditions were brutal. Finding toilet paper was a daily challenge. The food wasn’t edible, so every meal meant finding food outside. He lived in a 10-by-10 room with three other people, and residents were regularly overdosing on K2.

“I really began to understand some of those real big challenges,” Jeff reflected. “So, again, these were learning experiences for me, but they also opened the door up for me to understand better how you begin to fix a system that’s horribly broken.”

Building Victory by Victory

Jeff approached his reentry with a simple philosophy: one victory per day. Maybe it was getting a pass for a job interview, finding a good meal, or conquering a personal fear. He started running the Ben Franklin Bridge in Philadelphia, which is over a mile up and down, to overcome his fear of heights.

“They were little ones, but they were also important for me to know that I wasn’t going to come back in one day. And it was going to take time. And I needed to be intentional about it,” he explained.

His first job was teaching GED math just a few blocks from the shelter, in one of the most challenging areas of Philadelphia. From there, he began networking and started justice-impacted programming. He founded the National Workforce Opportunity Network with a colleague, focusing on helping people find careers rather than just jobs.

After three and a half years, Jeff landed a position as executive director over justice programs at JVS Human Services, a $800 million nonprofit that had been around for 70 years. This opened doors he never expected. The Pennsylvania Attorney General’s office asked him to join the Pennsylvania Reentry Council. He took a seat on the Pennsylvania Workforce Development Board. The Coalition on Adult Basic Education asked him to start their Prison Literacy Committee nationally.

Leading Change as CEO of PD Green

Today, Jeff serves as CEO of PD Green, an organization that educates people impacted by the justice system. They provide tutoring inside and outside of prisons and jails across the country and operate in over 1,100 facilities.

Jeff has become a sought-after speaker, giving around 40 keynote addresses last year as a subject matter expert for the U.S. Department of Education. When he spoke at the U.S. Chamber of Commerce in Washington, he didn’t hold back with employers interested in hiring justice-impacted people.

“You’re the wrong people in this room,” he told them. “If you really want to learn how to hire talented people that are just as impacted, then we need to see your HR people in this room, because they’re the ones doing the actual hiring.”

Jeff emphasizes that employers can teach anyone to do almost any job, but they struggle with what he calls “essential skills.” These include showing up on time, managing conflict, and basic workplace behavior. He also advocates for understanding the 14,000 documented barriers that people face when reentering society.

Returning to prisons as a free man still makes Jeff nervous, but he values the opportunity to show current inmates that transformation is possible. His story demonstrates that even from the depths of a homeless shelter, it’s possible to rebuild not just a life, but a purpose-driven career dedicated to systemic change.