Supreme Court decision threatens Anthony Bailey’s release

Anthony Bailey, a 61-year-old Indianapolis bus driver and grandfather, was freed after serving 27 years in federal prison. Now, after a Supreme Court ruling narrowed compassionate release and the Justice Department moved to challenge similar early-release case

On an afternoon that should have felt ordinary, Anthony Bailey looked ahead to the life he built after prison—and tried not to dwell on what could be taken away.

In a May 2025 photo, Bailey, 61, is seen holding one of his grandchildren. Two years earlier, a judge had freed him after 27 years in the federal penitentiary, giving him a second chance. Since then. Bailey has been driving a city bus in Indianapolis for long hours and spending time with family at barbecues and card games.

Now that second chance is being tested. After a Supreme Court ruling in late May limited how prisoners can use the compassionate release program, and after a legal move by the Justice Department, Bailey is facing a return 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.”

His case is one of about a dozen that could be directly affected by the Supreme Court’s decision. The high court said the compassionate release program. meant for extraordinary or compelling circumstances. is designed for scenarios such as severe illness or old age. In the court’s majority view. inmates serving much longer sentences than the punishments they would receive today are not automatically eligible for early release just because of that gap.

The ruling has sharp edges, and the fight around it has become personal for Bailey and others who were seeking freedom after decades behind bars.

Retired federal Judge John Gleeson disagrees with the Supreme Court’s approach. “These are indefensibly long sentences, and they need to be corrected,” he said. Gleeson launched a pro bono program that has helped more than 100 people in prison petition the courts for early release. Most of the inmates assisted are Black men who used a gun in connection with other crimes. Prosecutors. according to the account of their cases. added severe mandatory penalties by stacking punishments—even in instances where no shots were fired—to build prison terms of 50. 60 or even 100 years.

Bailey’s own history illustrates what prosecutors said they were fighting over—and what his supporters say has already been resolved through time served.

On Sept. 3, 1997, Bailey and two other men robbed a bank and then carried out two carjackings. Prosecutors said in court papers that his crimes were serious and put several people in danger, including a school-age girl. Bailey later said: “Something that I totally regrets — will never happen again, ever, in life.”.

After the crimes, Bailey spent most of his time in the federal prison in Terre Haute, Indiana, where he worked as a barber. He was able to do that job for years, his record inside prison described as clean for decades, with just one minor infraction mentioned in court filings.

Maryam Kanna, a pro bono lawyer for Bailey, argued that Bailey has already served more time than most people convicted of federal murder. Kanna said Bailey has “a stable, happy life” and is “a really productive member of society,” adding that “the idea that he poses a danger is completely farcical.”

As the legal battle returns to court, prosecutors are signaling that they could move soon to send Bailey back to serve the rest of his long sentence. In Bailey’s case, that would mean a release date in 2050, when he is nearly 86 years old.

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.

The underlying issue reaches beyond Bailey’s record and into federal law itself. Congress has since lightened some of the harsh mandatory penalties that applied to Bailey and others convicted back in the 1990s. But lawmakers did not make the change retroactive, so people already serving time were not automatically swept in. The Supreme Court ruling. in turn. held that this means those prisoners’ punishments are not extraordinary or compelling under the compassionate release program’s standards.

Bailey said he would abide by the law. “OK, just got to keep fighting,” he said.

There are still signs of stability in his current life. and his probation officer had told him before the Supreme Court decision that she would recommend his early release from probation this fall. Bailey is not sure what his future holds in September. but he has continued to make use of the days he has.

His days are filled with family moments—barbecues. card games. and time in the park—along with small lessons that mark how far he has come since his release in July 2024. He has been showing his 4-year-old grandson the ropes: teaching him how to mow the lawn and taking him as a treat to enjoy the boy’s favorite food. french fries at McDonald’s.

“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.

For Bailey, that routine is more than time together. It’s a life he built with discipline and patience. Now the courts are asking him to stand in a legal storm he thought he had already survived. as his freedom hangs on whether the compassionate release path still leaves room for someone who has spent decades paying his debt and returned home to work. parent. and try to be useful again.

Anthony Bailey Supreme Court compassionate release Justice Department federal prison Indianapolis bus driver Terre Haute Maryam Kanna John Gleeson mandatory penalties federal sentencing