A judge freed Anthony Bailey in July 2024 after 27 years in federal prison, giving him a second chance. Bailey, now 61, has spent the past two years working as a city bus driver in Indianapolis, attending family barbecues, playing card games with relatives, and teaching his 4-year-old grandson how to mow the lawn.
But a Supreme Court decision in late May and a legal move by the Justice Department could send him back to prison in a matter of weeks.
“I’m hoping and praying that everything turn out and I get my life back,” Bailey said in an interview. “Today, right now, I’m a better person — I’m a productive citizen, I work hard.”
The high court ruled that the compassionate release program, which allows prisoners to petition for early release due to extraordinary or compelling circumstances, is designed for such things as severe illness or old age. The majority held that inmates serving much longer sentences than the punishments they would receive under current laws are not automatically eligible for the program.
Congress has since lightened some of the harsh mandatory penalties that applied to Bailey and others convicted in the 1990s, but did not make those changes retroactive. The Supreme Court said that means those sentences are not extraordinary or compelling for purposes of compassionate release.
Bailey was sentenced to decades in prison after a 1997 bank robbery and two carjackings. Prosecutors said his crimes were serious and put several people in danger, including a school-age girl. Under the mandatory-penalty rules at the time, prosecutors added severe firearms enhancements and stacked them, even though no shots were fired, producing a sentence that would have released Bailey in 2050, when he would be nearly 86.
“Something that I totally regrets — will never happen again, ever, in life,” Bailey said of his crimes.
During his time at the federal prison in Terre Haute, Indiana, Bailey worked as a barber. His record was clean for decades, with only one minor infraction mentioned in court filings.
Pro bono lawyer Maryam Kanna, who represents Bailey, noted 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 said.
Prosecutors are now signaling they could move soon to send Bailey back. The U.S. attorney’s office in the Southern District of Indiana, where Bailey’s case is pending, declined to comment through a spokesperson, who said the office speaks only through official court filings.
Retired federal Judge John Gleeson, who launched the pro bono program that helped Bailey and more than 100 others petition for early release, criticized the Supreme Court’s ruling. “These are indefensibly long sentences, and they need to be corrected,” Gleeson said. He noted that most of the inmates his program helps are Black men who used a gun in connection with other crimes and received stacked mandatory penalties that produced prison terms of 50, 60 or even 100 years.
Bailey said he would abide by the law. “OK, just got to keep fighting,” he said.
Before the Supreme Court decision, Bailey’s probation officer had told him she would recommend his early release from probation this fall. Now he is not sure where he will be in September. He is making the most of his time, enjoying family barbecues and card games in the park and showing his grandson the ropes.
“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.
He is teaching his grandson how to mow the lawn and, as a treat, taking him to get french fries at McDonald’s.