Life After Release
Anthony Bailey, 61, was released two years ago after serving 27 years in federal prison. Since then, he has embraced life outside, driving a city bus in Indianapolis and spending time with his family. He enjoys barbecues and card games, building strong community ties.
Facing Imminent Reincarceration
Bailey’s future now hangs in the balance. A Supreme Court ruling and Justice Department action threaten to revoke his freedom. His is one of several cases affected by the May ruling that changed compassionate release conditions. This program was intended for extraordinary cases like serious illness or old age, not automatically applicable for inmates with sentences harsh by today’s standards.
Dispute Over Sentences
Retired Judge John Gleeson opposes the ruling. He argues these long sentences need correction, launching a program to help inmates petition for early release. Most affected are Black men whose cases involved stacked mandatory penalties, leading to excessively long terms.
Bailey’s Past
In September 1997, Bailey, accompanied by two others, committed bank robbery and carjackings. These crimes endangered many, including a schoolgirl. Reflecting on his past, Bailey expressed regret and vowed it would never happen again.
Efforts for Reconciliation
While incarcerated, Bailey worked as a barber without a major incident on record. Maryam Kanna, his pro bono attorney, highlighted he has served longer than many convicted of federal murder. She describes Bailey as a stable, productive citizen, arguing his danger is exaggerated.
Changing Laws, Retroactive Application Lacking
Despite legislative changes easing prior harsh penalties like those Bailey faced, they lack retroactive application. Consequently, the Supreme Court’s decision deems their cases as insufficiently extraordinary, disqualifying them from compassionate release considerations.
Bailey’s Commitment to Law
Bailey remains law-abiding, working toward potential early release from probation, which seemed promising before the Supreme Court ruling. He continues to enjoy his remaining free time with family, particularly teaching his grandson everyday tasks and indulging in special outings for his grandson’s preferred fries from McDonald’s.

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