In 2018, President Trump signed the First Step Act. This bipartisan criminal justice legislation reduced mandatory sentences formerly required by federal firearms law 18 U.S.C. Section 924(c). The First Step Act also prevented the sentences issued under 924(c) from being mandatorily “stacked” to run consecutively. Prior to The First Step Act, judges were required to issue long mandatory sentences, consecutively served, for multiple criminal counts. This resulted in some sentences for armed robbery being longer than the sentences in the same district for murder.

John Gleeson, for 22 years a U.S. District Court Judge in Brooklyn, New York, handed down these long prison sentences. Near the end of his years as a federal judge, Mr. Gleeson became concerned with some of the stacked sentences he had issued during his tenure. In particular, he had sentenced convicted carjacker Francois Holloway to 57 years in prison in 1996.

Mr. Holloway filed a motion to reopen his case. When Judge Gleeson reviewed the case, he was disturbed by the harsh mandatory sentence. He persuaded U.S. Attorney Loretta Lynch in Brooklyn to open the case and then to vacate two counts of Mr. Holloway’s conviction so he could have a “more just sentencing.” Mr. Holloway’s sentence was reduced to time served, and he was released from prison. One of the elements Judge Gleeson stressed during the proposal for resentencing was Mr. Holloway’s determination to better himself while in prison.

The Holloway Doctrine was born from these events. The doctrine recognizes that courts have the discretion to reduce a sentence in the interest of fairness “even after all appeals and collateral attacks have been exhausted and there is neither a claim of innocence nor any defect in the conviction or sentence.” But the Holloway doctrine only applies if the government agrees to a reduced sentence. Several incarcerated inmates have been released based upon the Holloway Doctrine.

But that’s not the end of the story. When Judge Gleeson retired from the bench (for financial reasons, he said), he joined the law firm of Debevoise & Plimpton. There, he has begun “The Holloway Project.” Together with lawyer Marisa Taney, he runs this pro bono project aimed at addressing race and equity in the criminal justice system.

Mr. Gleeson and Ms. Taney screen cases that involved the mandatory sentencing laws. Mr. Gleeson says they look for people convicted under the federal firearm statute with long sentences after trial. He also looks for those inmates with good behavior and good prison records.

One inmate, Todd Ellerby, wrote four times to Mr. Gleeson before getting a response. Mr. Gleeson reported that he rejects ten cases for each one they take on. Mr. Ellerby was charged in 1995 for brandishing a gun while robbing credit unions and banks. He also threatened employees and used handcuffs and duct tape to restrain them. A judge sentenced him to 52 years and three months in prison.

When Mr. Ellerby heard about the Holloway case, he began writing letters to Mr. Gleeson. Mr. Gleeson and Ms. Taney filed a motion in January of 2020 arguing for Mr. Ellerby’s release. On September 11, U.S. District Judge Carol Bagley Amon decided that the 25 years and eight months Mr. Ellerby had already served were sufficient. He was released from federal prison; the deadline for federal prosecutors to appeal the decision has passed.

Not everyone is enthusiastic about Mr. Gleeson’s crusade. U.S. Attorney John Huber of Utah wrote the judge presiding over some of Mr. Gleeson’s cases to say that the early release of an inmate who “had committed his robberies for the thrill of violence” would set a dangerous precedent.

In addition to adjusting sentencing, The First Step Act also changed compassionate release. Before the Act, compassionate releases were allowed for “compelling” reasons such as a medical condition or old age, though most requests were denied. Now inmates can appeal to a judge after the prison officials reject their requests. Mr. Gleeson and Ms. Taney are stretching the interpretation of “extraordinary and compelling” to include harsh mandatory sentences. They insist that the elimination of those harsh mandatory sentences from the law is a valid reason for compassionate release.

The First Step Act doesn’t mention compassionate release in conjunction with 924(c) sentences, but Mr. Gleeson said, “We realized, holy tamoley, we got an avenue.”

The Holloway Project’s record so far: eight wins in district courts, five losses in district courts. They have nine active appeals, not all brought by them; some are filed by others. Federal prosecutors oppose the motions. They say that judges weren’t given the authority under the First Step act to release such offenders. The law eliminated some sentencing requirements for future offenders, they say, but current inmates are not included in the reduced sentences.

Mr. Gleeson received his undergraduate degree from Georgetown in 1974 and his JD from Virginia School of Law in 1980. He was a law clerk in 1980-1981, in private practice from 1981-1985, and then was an Assistant U.S. Attorney from 1985 to 1994, with a specialty in pursuing Mafia cases. He was appointed by President Clinton on July 22, 1994, to his Judgeship, where he served for 22 years. He is now helping to correct the perceived injustices he carried out by law during his years as a U.S. District Court Judge, Eastern District of New York.