Anthony Bailey, 61, has spent the past two years rebuilding his life outside federal prison. He drives a city bus in Indianapolis, attends family barbecues and plays card games with relatives. He is also raising his 4-year-old grandson, teaching him to mow the lawn and taking him for french fries at McDonald's. Now, after a Supreme Court ruling in late May and subsequent action by the Justice Department, Bailey faces a return to prison within weeks to finish a sentence that would not release him until 2050, when he is nearly 86 years old.
Bailey's case is among roughly a dozen that could be directly affected by the court's decision limiting how prisoners can use the compassionate release program. The program was designed for extraordinary or compelling circumstances such as severe illness or advanced age. In its majority opinion, the court found that inmates serving much longer sentences than they would receive under current law were not automatically eligible for early release through this pathway.
What the Left Is Saying
Retired federal Judge John Gleeson criticized the Supreme Court's ruling and has launched a pro bono program that has helped more than 100 people in prison petition for early release. 'These are indefensibly long sentences, and they need to be corrected,' Gleeson said. Most of those his program has assisted are Black men who used a gun in connection with other crimes, he noted, adding that prosecutors stacked severe mandatory penalties onto their cases — even when no shots were fired — building prison terms of 50, 60 or even 100 years.
Bailey's pro bono attorney, Maryam Kanna, argued his case exemplifies why the ruling is flawed. '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. She pointed out that Bailey has already served more time than most people convicted of federal murder.
Bailey himself expressed hope for a different outcome while affirming his commitment to following whatever the law requires. 'I'm hoping and praying that everything turn out and I get my life back,' he said in an interview. 'Today, right now, I'm a better person — I'm a productive citizen, I work hard.'
What the Right Is Saying
The Supreme Court's majority opinion held that the compassionate release program's requirement for extraordinary or compelling circumstances does not automatically extend to inmates whose sentences are longer than what current law would prescribe. Congress has since lightened some of the harsh mandatory penalties that applied to Bailey and others convicted in the 1990s, but lawmakers did not make those changes retroactive.
Prosecutors with the U.S. attorney's office for the Southern District of Indiana — where Bailey's case is pending — have signaled they could move soon to return him to prison to serve the remainder of his original sentence. Kelsie Clayton, a spokesperson for that office, said the office speaks only through official court filings.
Bailey acknowledged he would abide by whatever the courts decide. 'OK, just got to keep fighting,' he said. His probation officer had previously told him she would recommend early release from supervision this fall before the Supreme Court decision. Now his status for September is uncertain.
What the Numbers Show
Bailey spent 27 years in federal prison — most of it at the facility in Terre Haute, Indiana, where he worked as a barber. Court filings show his record inside was clean for decades with just one minor infraction noted.
On Sept. 3, 1997, Bailey and two other men robbed a bank and then carried out two carjackings. Prosecutors said in court papers that the crimes were serious and put several people in danger, including a school-age girl. Bailey described his actions as something he 'totally regrets — will never happen again, ever, in life.'
If returned to prison, Bailey would not be released until approximately 2050 under the terms of his original sentence.
The Bottom Line
The Supreme Court's ruling creates uncertainty for roughly a dozen inmates like Bailey who received compassionate release before the decision and now face potential reimprisonment. Prosecutors in Bailey's case have indicated they could act soon to return him to custody.
Bailey said he is making the most of his current freedom, enjoying time with family including his grandson while awaiting word on his legal standing. His attorney has filed paperwork challenging any attempt to reincarcerate him. What happens next will likely depend on how courts interpret the Supreme Court's ruling in individual cases — and whether Congress takes any action to address inmates whose sentences fall into this gap between old mandatory minimums and current law.