Two years after walking free from federal prison, Anthony Bailey has constructed a new life in Indianapolis. The 61-year-old drives a city bus, attends family barbecues, and teaches his 4-year-old grandson how to mow the lawn. However, a recent Supreme Court ruling threatens to dismantle everything he has built, potentially returning him to prison for decades.
Bailey was released in July 2024 after serving 27 years in the federal penitentiary. A judge granted him early release through the compassionate release program, designed for extraordinary or compelling circumstances. Since his release, Bailey has maintained a clean record, working long hours and developing deep roots in the Indianapolis community.
"I'm hoping and praying that everything turn out and I get my life back," Bailey said, speaking to NPR. "Today, right now, I'm a better person — I'm a productive citizen, I work hard."
The threat to Bailey's freedom stems from a Supreme Court ruling issued in late May that significantly narrowed the scope of the compassionate release program. The high court determined that the program should cover circumstances such as severe illness or old age, but ruled that inmates serving sentences much longer than current punishments would receive are not automatically eligible for early release.
Bailey's case is among approximately a dozen directly affected by this decision. Following the ruling, the Justice Department has taken legal action that could force Bailey to return to prison within weeks to complete his original sentence, which would keep him incarcerated until 2050, when he would be nearly 86 years old.
The circumstances that led to Bailey's lengthy sentence date back to September 3, 1997. On that day, Bailey and two other men robbed a bank and subsequently carried out two carjackings. Prosecutors noted in court papers that his crimes were serious and endangered several people, including a school-age girl.
"Something that I totally regrets — will never happen again, ever, in life," Bailey told NPR.
Bailey spent most of his incarceration at the federal prison in Terre Haute, Indiana, where he worked as a barber. The position gave him access to scissors and other sharp tools, demonstrating the trust prison officials placed in him. His record inside prison remained clean for decades, with only one minor infraction mentioned in court filings.
The severity of Bailey's sentence reflects the harsh mandatory penalties that were common in the 1990s. Most of those inmates affected by such penalties are Black men who used a gun in connection with other crimes. Prosecutors added severe mandatory penalties to their cases, stacking those punishments even if no shots were fired, resulting in prison terms of 50, 60, or even 100 years.
Maryam Kanna, a pro bono lawyer representing Bailey, emphasized that he has already served more time than most people convicted of federal murder. "He has a stable, happy life and is a really productive member of society, so I mean, the idea that he poses a danger is completely farcical," Kanna told NPR.
Retired federal Judge John Gleeson, who launched a pro bono program that has helped more than 100 people in prison petition the courts for early release, strongly disagrees with the Supreme Court ruling. "These are indefensibly long sentences, and they need to be corrected," he said, speaking to NPR.
Congress has since lightened some of the harsh mandatory penalties that applied to Bailey and others convicted in the 1990s. However, lawmakers did not make that change retroactive to apply to people already inside prison. The Supreme Court's ruling interprets this to mean that such sentences are not extraordinary or compelling under the compassionate release program's requirements.
Prosecutors are now signaling that they could move soon to send Bailey back to serve the remainder of his sentence. Kelsie Clayton, a spokesperson for the U.S. attorney in the Southern District of Indiana, where Bailey's case is pending, said the office speaks only through official court filings.
Before the Supreme Court decision, Bailey had been receiving positive evaluations from his probation officer, who indicated she would recommend his early release from probation this fall. Bailey said he would abide by the law. "OK, just got to keep fighting," he told NPR.
As uncertainty looms over his future, Bailey continues to make the most of his time with family. He enjoys barbecues and card games in the park, and has developed a special bond with his young grandson, who eagerly participates in everyday tasks.
"He's a worker, you know. Everything I do — he sit there and just watch and then he [asks], 'We washing the car?' Or, 'We taking the trash out?' Like, yeah, c'mon," Bailey said, describing his grandson to NPR.
Bailey has been teaching his grandson how to mow the lawn and, as a treat, taking him to enjoy the boy's favorite food: french fries at McDonald's. These simple moments now carry profound weight as Bailey faces the possibility of losing his freedom once again, uncertain where he will be in September.
