Anthony Bailey, aged 61, cherishes moments with his grandchildren. A photo taken in May 2025 captures such a memory, illustrating the family ties Bailey has embraced following his early release from a federal prison two years ago. After serving 27 years, Bailey began rebuilding his life, driving a city bus in Indianapolis and enjoying family gatherings and card games.
Bailey now faces an uncertain future due to a Supreme Court ruling and actions by the Justice Department that may lead to his return to prison shortly. The ruling, from late May, restricts the use of the compassionate release program. The program is limited to prisoners facing severe illness or advanced age for release.
“I hope and pray everything gets better and I regain my life,” Bailey shared in an interview. “Today, I am a better person, a productive citizen who works hard.”
Bailey’s case exemplifies a broader legal challenge. Retired federal Judge John Gleeson advocates for more leniency in sentences. He initiated a pro bono program helping over 100 inmates, primarily Black men who committed crimes with firearms. Prosecutors imposed harsh mandatory penalties, leading to prolonged sentences.
In Bailey’s situation, he participated in a bank robbery and two carjackings in September 1997. These offenses placed many, including a young girl, in danger. Reflecting on his past, Bailey expressed remorse, stating, “Something I completely regret—it will never happen again.” While at the Terre Haute federal prison, Bailey maintained a clean record, working as a barber and incurring minimal infractions.
Maryam Kanna, Bailey’s pro bono lawyer, argued for his release. She emphasized that Bailey has outlived the typical time served for more severe crimes, asserting that he leads a stable and productive life. “The notion that he poses a danger is absurd,” Kanna stated.
Despite changes in laws reducing harsh penalties from the past, these adjustments were not applied retroactively. A spokesperson for the U.S. Attorney’s office in Southern Indiana maintained their position only via official court documents. Bailey’s sentence, as per current laws, projects release at age 86 in 2050.
Bailey remains committed to lawful compliance. He received positive feedback from his probation officer, who supported early release from probation this autumn. The Supreme Court’s decision altered his certainty about September, but he continues cherishing time with family.
Connecting with his 4-year-old grandson, Bailey shares life lessons. While teaching yard work, Bailey delights in his grandson’s constant curiosity about tasks, from washing cars to taking out trash. He rewards such diligence with trips to McDonald’s for the boy’s favorite, french fries.