President Trump sought office as a tough-on-crime candidate who would restore respect for the police and crush urban criminality. But in office, he has released felons and helped pass legislation shortening prison sentences.
Trump’s potentially contradictory impulses for law and order but also second chances face a looming political test when about 4,000 federal inmates are released in July under an expansion of “good time” credit in the First Step Act, which he signed in December.
Reform advocates say it’s successful reentry into society for the looming wave must be assured. Otherwise, the reform cause and its political backers, including Trump, could be damaged.
Many conservatives and the Fraternal Order of Police backed the new law, but it was opposed by other law enforcement groups and 12 GOP senators. Because of Republican divisions, it nearly died before Trump called on Senate Majority Leader Mitch McConnell to allow a vote.
“There’s a lot of concern that they have to get this right. Folks like Tom Cotton are just waiting for someone to do something stupid,” a source who has worked on White House efforts recently told the Washington Examiner.
The wave had been expected in December. But a drafting error placed the “good time” credit expansion — allowing an extra seven days a year — in an unrelated section of the law featuring a seven-month delay.
Some inmates who expected near-immediate release have been transferred to halfway homes, as is typical at the end of federal sentences.
Veda Ajamu’s brother Robert Shipp, 46, is in a Chicago halfway house after serving 25 years of a federal drug sentence. Shipp, who can leave in July, works part-time but must pay 25% of his minimum-wage earnings to the halfway house.
“He has us, and that’s it. I would consider him one of the fortunate ones because he has family. But he is also starting from scratch,” said Ajamu, who started a GoFundMe page to help her brother.
Ajamu said reform groups should provide support to people being released, especially if they fundraised off them. Failures could undermine further reform, she warned.
“Unless there are some real reentry things put into place for them, then people, if they don’t have anything, unfortunately, they resort to what they know,” Ajamu said.
Between December and April, the First Step Act allowed 643 people to leave prison early under reductions for crack cocaine and compassionate release. But the future releases will come all at once.
“We have really been focused on when this day would come,” said Mark Holden, general counsel of Koch Industries, which has worked with the Society for Human Resource Management to encourage employers to hire former inmates.
Holden believes Trump will actively use his bully pulpit to encourage employers to hire ex-cons, something he already routinely does. Holden’s group has compiled a list of employers open to hiring former inmates.
Trump son-in-law and adviser Jared Kushner, who engineered the First Step Act, has been working to encourage companies. In February, Kushner called Walmart CEO Doug McMillon and asked him to help recently released Catherine Toney and others find work.
Pat Nolan, director of the American Conservative Union Foundation’s Center for Criminal Justice Reform, said churches will play a key role.
“The greater the number of moral, upstanding citizens we can pair with returning inmates, the better the chances they have,” Nolan said, arguing, “this is not going to be some wave of violent felons across the U.S. running rampant.”
Joe Luppino-Esposito, director of rule of law initiatives at the Due Process Institute, said the size of the wave is important to keep in context. “There are 3,000 to 4,000 inmates released every month as their sentences end,” he said.
Still, Luppino-Esposito said that “it will be important for advocates around the country to step up and help these people return to society and lead productive, crime-free lives.”
Matthew Charles, a guest of Trump’s at the State of the Union, had trouble finding housing after his release under the First Step Act, Luppino-Esposito noted.
For now, advocates for the reforms remain hopeful.
Kevin Ring, president of Families Against Mandatory Minimums and a former Republican congressional staffer, said, “I suppose everyone who supports it is on the hook for its success and failure.”
But Ring points to a U.S. Sentencing Commission study that found a 2007 law shortening crack cocaine sentences did not increase recidivism.
“We can’t live in a zero-risk world unless we drop the speed limit to 10 mph. The idea that if one person commits a crime and 3,500 live productive lives with their families, that this is a failure — it doesn’t make sense,” he said.
A White House spokesman did not respond to requests for comment for this story.

