Damon Davis’ future looked grim. He didn’t learn to read until the third grade and was homeless on and off throughout his childhood. Still, he was the first in his family to graduate from high school, despite having a low GPA.

After graduation, he took a job at an Amazon warehouse but was soon put on short-term disability resulting from a knee injury. He also faced eviction. Davis, who was living in Lexington, Kentucky, turned to the one thing he was comfortable with–selling drugs–and was arrested in 2008.

Davis, now 47, served a 52-month sentence for a crime he admits having committed.

About six months into his federal prison sentence at the Federal Correctional Institute Ashland, Davis was approached by a fellow inmate who was helping other prisoners with their appeals. The man asked Davis for help with research, and Davis obliged. After helping three inmates pass the GED and poring over appeals, trial transcripts and tons of flimsy attorney notes for others in prison, Davis became motivated to help himself.

In 2013, after he was released–homeless with $26 in cash–Davis found a job at a JIF peanut butter plant in Lexington, which he took because the position offered full tuition reimbursement. He continued working the overnight shift at the factory while taking classes at a local community college during the day and snagging sleep via naps whenever he got a chance. After a year, Davis enrolled in the University of Kentucky and then the University of Cincinnati Law School.

“The guys I helped when I would pore through their transcripts–you would see how poor the level of defense was,” Davis says regarding his time as a jailhouse lawyer. “If you’ve done it as an inmate, you’re really practicing law, but it’s not official.”

But there’s a big difference between giving unlicensed legal advice to prisoners and working as a lawyer at a law firm. Would anyone hire him? Was he even legally allowed to practice?

Each state sets its own rules for formerly incarcerated people who want to practice law. In Kansas, Mississippi and Texas, for example, no one with a felony can practice law.

Puerto Rico makes it much easier for those with criminal records to practice law with the decision this year allowing incarcerated students to enroll in a JD program as part of an agreement between the University of Puerto Rico and the Department of Corrections and Rehabilitation. But even for those who live in less restrictive states, there are other hurdles to overcome.

In the character and fitness section of law school applications, most ask prospective students whether they have been convicted, placed on probation or given a deferred adjudication or other program for a criminal offense. Further examination usually follows if this applies, which may affect their admission.

Even after graduating from law school, students with criminal records face other challenges before being allowed to practice.

Davis was living in Ohio, where the Supreme Court of Ohio’s Board of Commissioners on Character and Fitness required him to undergo a background check, supply character references and evidence that he changed his ways so he could take the bar exam.

When Davis graduated law school in 2022, the board asked him questions about his support system, his fitness level and his interest in different areas of law, which was a requirement for being granted a law license. He passed the evaluation and the bar exam, and he started practicing at the Hamilton County Public Defender’s office in Cincinnati where he had done a previous internship.

His path to the bar was relatively easy, compared with Jonas Caballero’s journey.

In 2002, Caballero was first arrested in Pittsburgh for failure to disperse during a protest against the war in Iraq. The charges were later dropped, and Caballero went on to graduate from the University of Pittsburgh summa cum laude in 2010. He then moved to England to attend the University of Cambridge on a Fulbright scholarship.

After receiving a master of philosophy degree from Cambridge, Caballero moved to New York City, where he began using meth, cocaine and alcohol to help him cope with depression and PTSD that stemmed from witnessing human rights abuses in the West Bank and from being shot by the Israel Defense Forces, he says. In 2017, he was arrested and charged with selling drugs.

In prison, Caballero says, he was sexually assaulted by a guard. He filed numerous grievances, which simply led to the guards further abusing him, he says. Caballero’s mother mailed him the Prisoners Self-Help Litigation Manual, and he became a jailhouse lawyer.

“I survived several motions to dismiss in two pro se cases I filed in the [Eastern District of New York], and eventually settled those cases,” he says.

After a female corrections officer violated his Fourth Amendment rights when she viewed him receiving a colonoscopy, Caballero filed a pro se lawsuit in the New York State Court of Claims and won on liability after conducting an in-person trial in Albany.

It was then that Caballero realized he could and should attend law school.

“Recognizing my knack for the law and my passion for defending human rights, especially those of prisoners and individuals affected by colonial occupation, I decided to pursue a legal education,” he says.

Daniel Bollana Jr., an assistant professor of law and director of Bar Success at Albany Law School where Caballero is studying, says incarcerated individuals like Jonas can make excellent attorneys because they understand the power and pain the justice system can bring. 

Caballero in particular, says Bollana, has a deep understanding of the mental, emotional, familial, professional and financial implications of civil and criminal actions.

“As an aside,” Bollana says, “Jonas is one of the most thoughtful, talented and professional students I’ve had an honor of working with in my legal career. He is someone I expect to rise very high in our profession and will be a leader in advocating for those who often are left behind by the justice system.”

Transitioning from incarceration to law school, however, posed significant challenges. Obstacles have included routine denial of medical benefits due to lingering inaccuracies in the system still marking him as incarcerated. Securing housing also has been difficult.

Despite being a Fulbright scholar, his formerly incarcerated status often overshadowed his achievements. “It felt as though admissions committees viewed me solely through the lens of my past mistakes,” he says.

He was rejected from all but two of the 10 law schools he applied to–and those two yielded waitlists.

Eventually, Caballero was able to attend Albany Law School at the age of 40 on a scholarship and is on track to graduate a semester early. He's also interning at the Abolitionist Law Center. 

Caballero is not alone in his struggle to transition out of prison–and some universities are attempting to ease this adjustment by launching programs specifically for incarcerated students.

Northwestern University rolled out a prison education program in 2018 to help prisoners earn bachelor’s degrees and currently has 80 men and 20 women enrolled. The first cohort of 16 students graduated Nov. 16, 2023, and one was accepted to Pritzker School of Law at Northwestern, says Jennifer Lackey, the director of Northwestern’s Prison Education Program.

“Offering educational opportunities to incarcerated people has been shown to be one of the most effective ways of positively intervening in the criminal legal system,” says Lackey.

In 2015, New York University also launched a prison education program offering free college courses to incarcerated and formerly incarcerated students at Wallkill Correctional Facility in New York State–but they have yet to have a student go on to become a lawyer. 

Still, prison education programs like these are few and far between, leaving most former prisoners to fend for themselves if they want to further their education.

Vincent T. O'Neil had his first misdemeanor criminal conviction at 16, and two drug felony convictions at 19 and 25. After his release from jail in 2017, O'Neil attended community college and decided to become an attorney because he felt he would understand his clients. He was accepted into Albany Law School while living in Henderson, Nevada.

“A former prisoner knows how debilitating the process of a criminal proceeding can be and how much small acts of kindness, empathy and solidarity can mean,” he says. “Throughout my legal troubles, I only had one defense attorney who asked about my well-being and the problems causing me to act out in the ways I did. As a formerly incarcerated person, I understand the life that leads up to a criminal conviction, and the circumstances that can cause a person to act illegally.”

O'Neil is in the process of securing internships and preparing for the either the New York or Minnesota Bar, the latter of which is more difficult for those with criminal records. “New York, thankfully, has a holistic approach to its character and fitness tests, but it will still require a lengthy process in terms of both time and application materials,” O’Neil says.

Regardless of the hurdles, a handful of former prisoners have gone on to excel in school and in their legal career.

Reginald Dwayne Betts is one of them. He was incarcerated at the age of 16 for armed carjacking in Springfield, Virginia, and was sentenced to nine years in prison (he served eight), including 14 months in solitary confinement at seven institutions, including a juvenile detention center and two prisons. He passed the time–especially while in solitary confinement–by reading. At the age of 24, in March 2005, Betts was released, and by 2009, he had a bachelor’s degree from the University of Maryland. He received a 168 on the LSAT and was admitted to Yale Law School. While in law school, Betts started helping his former prisoner friends and managed to get six of them out of prison.

“I dreamed of doing something absurd,” Betts says. “The audacity of thinking you could go into the legal world as a criminal? We’re chasing the American dream. What if the American dream is about redemption?”

Updated on Oct. 30 to clarify information about Vincent T. O'Neil.