WASHINGTON ― In one of his final acts in office, President Barack Obama granted clemency to 209 federal prisoners on Tuesday, almost all of whom were convicted of drug crimes.

Obama has now granted more commutations than any president in American history, according to White House Counsel Neil Eggleston. The number of federal prisoners who have had their sentences commuted during Obama’s presidency totals 1,385 individuals, though many of those who had their sentences shortened will spend several more years behind bars. The latest group includes more than 100 individuals who believed they would die in prison, as they’re serving life sentences, according to the White House.

Most famously, the group included Chelsea Manning, the former Army intelligence analyst convicted of leaking a giant trove of government documents to WikiLeaks. Manning, a transgender woman who had been pushing the Army to allow her to have sex reassignment surgery to treat her gender dysphoria, will now be released in May.

Oscar López Rivera, who was part of a militant group fighting for Puerto Rican independence and has been in prison since 1981, was also granted clemency. His clemency case had been pushed by South African anti-apartheid icon Archbishop Desmond Tutu, independent Sen. Bernie Sanders and “Hamilton” creator Lin-Manuel Miranda, according to NPR. Rivera is 74-years-old.

In another case, Obama commuted the death sentence of an intellectually disabled man to life in prison. The man, Arboleda Ortiz, was convicted of aiding and abetting murder in relation of a drug trafficking crime.

“We commend President Obama for making history by continuing to grant hundreds of clemencies,” Jessica Jackson Sloan, the national director of #cut50, said in a statement. “For far too long, efforts to fight crime have missed their mark, breaking up families and harming the human potential in our most vulnerable communities. Thanks to President Obama’s clemency initiative, more than one thousand people who were given overly harsh sentences during the War on Drugs now have a second chance at freedom.”

“President Obama has again used commutation to reunite families,” Cynthia W. Roseberry, project manager for Clemency Project 2014, said in a statement. “We are grateful to President Obama, and we are hopeful for more commutations in his final days in office.”

The White House made the sentence commutation announcement at the same time as it announced the pardoning of 64 individuals, including the former owner of Studio 54 as well as retired Gen. James Cartwright, who had been accused of lying to the FBI about contacts with reporters.