DOJ Moves to Undo Tony Bailey's Release After Supreme Court Ruling

Federal prosecutors in Indiana are seeking to reverse the 2024 court order that freed Anthony "Tony" Bailey, 61, after nearly 27 years in prison, a move that gained new legal momentum when the U.S. Supreme Court, on May 28, 2026, invalidated the sentencing guideline provision that was the principal foundation of his release.

A 1997 Crime Spree and a 60-Year Sentence

On September 3, 1997, Bailey and two accomplices, Jerry Jones and Gregory Jones, seized a UPS truck and driver in Indiana, used the vehicle and a stolen uniform to rob the Chesterfield branch of National City Bank of Indiana, stealing $105,691, then crossed an interstate median into opposing lanes before crashing into a ditch and fleeing into an adjacent cornfield.

They then entered the nearby home of the Routte family at gunpoint, restrained the mother and teenage daughter, and forced the father to drive them to Indianapolis. According to the Seventh Circuit's 2026 co-defendant opinion, Jones told Sherry Routte he would kill her husband if she called police. A federal jury convicted Bailey on all six counts, armed bank robbery, two carjackings, and three firearm offenses under 18 U.S.C. § 924(c).

At sentencing in May 1998, the court imposed an aggregate term of 728 months, 60 years and eight months. The bulk of that total came from the way the law treated multiple § 924(c) convictions in a single prosecution: Bailey received a consecutive 5-year term on the first count, then 20-year terms on each of the next two, a practice known as "stacking." Those three consecutive firearm penalties alone accounted for 540 months of his sentence.

The 2024 Reduction

In December 2018, Congress passed the First Step Act, which changed when the heavier § 924(c) recidivist penalty could apply, but it did not make the change retroactive for people already sentenced. Bailey's 728-month term therefore remained in place.

In November 2023, Bailey filed a new motion for compassionate release under a recently updated U.S. Sentencing Commission policy. Amendment 814, which took effect that month, added a provision, § 1B1.13(b)(6), allowing courts to treat an unusually long sentence and a substantial disparity created by a nonretroactive statutory change as extraordinary and compelling grounds for release, provided the prisoner had served at least ten years.

U.S. District Judge Richard L. Young, reviewing the motion in the Southern District of Indiana, calculated that under current § 924(c) treatment Bailey's firearm terms would total 180 months rather than 540, a difference of 360 months, or exactly 30 years. On May 20, 2024, the judge reduced Bailey's custodial sentence from 728 to 368 months, found that Bailey no longer posed a danger to the community, and concluded the sentencing factors under 18 U.S.C. § 3553(a) supported relief. The order allowed up to 14 days for release arrangements to be made. Bailey was released in July 2024.

According to WTHR, he subsequently found work as a full-time driver for IndyGo, Indianapolis's public transit system, and rebuilt relationships with his eight grandchildren and five great-grandchildren. NPR reporting separately confirmed his work as a city bus driver in Indianapolis and described him spending time with his family.

The Supreme Court Ruling Undercutting His Release

On May 28, 2026, the Supreme Court issued its decision in Rutherford v. United States, Nos. 24-820 and 24-860. By a 6–3 vote, the Court held that when Congress deliberately makes a sentencing change nonretroactive, the sentencing disparity that results cannot serve as an extraordinary and compelling reason for compassionate release, whether considered alone or alongside other factors. Justice Amy Coney Barrett wrote the majority, Justices Alito, Thomas, Gorsuch, Kavanaugh, and Chief Justice Roberts joined. Justice Sonia Sotomayor dissented, joined by Justices Kagan and Jackson.

The ruling invalidated § 1B1.13(b)(6) of the Sentencing Guidelines to the extent it authorized use of a deliberately nonretroactive sentencing change as compassionate-release eligibility grounds, precisely the provision Judge Young had cited as the principal legal basis for Bailey's 2024 reduction.

What the Appeal Could Mean for Bailey

The U.S. Attorney's Office for the Southern District of Indiana had appealed the 2024 reduction order even before the Supreme Court acted. WTHR reported on June 26, 2026 that an assistant U.S. attorney sent Bailey's legal team an email in the days prior, reaffirming plans to seek reversal in light of Rutherford. That email and the current appellate docket were not independently confirmed through official public court records as of this writing.

What Rutherford does not do, on its own, is automatically reinstate the original 728-month term. Reincarceration would require a court to vacate or modify Judge Young's reduction order and issue a specific directive. The district court's 2024 order also noted Bailey's rehabilitation record and health-related arguments, though the judge did not formally resolve those alternative grounds after finding the sentencing disparity alone sufficient. Whether those remaining arguments could provide independent support for compassionate release is a question the courts have yet to answer in Bailey's specific case.

If the reduction were vacated without any alternative relief, Bailey's projected release date under the original sentence would revert to March 28, 2050, as recorded in the May 2024 court order.

John Gleeson, a former federal district judge who now runs the Holloway Project, which advocates sentence reductions for people serving exceptionally long federal terms, has been involved in Bailey's case alongside attorney Maryam Kanna. According to Gleeson's Debevoise & Plimpton biography, the project has focused heavily on the consequences of pre-First Step Act § 924(c) stacking. NPR reported that about a dozen people could face similar legal exposure after Rutherford.

The U.S. Sentencing Commission's Annual Report for fiscal 2025 puts the average federal murder sentence at 286 months, roughly 24 years. Bailey's original 728-month firearm-and-robbery term was more than double that figure, though the offenses are not directly comparable given the multiple counts and mandatory consecutive terms involved.

A Victim's Relative Speaks

WTHR reported that Allison Short, whose mother and grandparents were among those held at gunpoint during the 1997 home invasion, said in an interview that she personally believed 27 years behind bars was enough. Most other victims' relatives did not respond to the broadcaster's requests for comment, and their views are not established in the public record.

What Comes Next

No accessible court order requiring Bailey to surrender had been issued as of June 27, 2026. The government's next procedural move, whether a formal appellate brief, a remand motion at the district level, or another action, had not been confirmed in an official public docket filing at the time of publication. The Seventh Circuit's handling of any post-Rutherford motion will determine whether Bailey remains free while the legal challenge proceeds or faces a return to custody during the review process.

WTHR reported that Bailey's attorneys have argued the ruling should not automatically erase the nearly two years he has spent outside prison while complying with his supervised release conditions.