President Trump signed executive orders aimed at increasing federal involvement in Washington D.C.'s criminal justice system, including measures to hold more individuals in federal custody and curb cashless bail practices. While supporters argue these steps enhance public safety by ensuring law enforcement accountability, critics warn they could increase pretrial detention unfairly and undermine reforms like the First Step Act. The move reflects ongoing political debates over crime policies, law enforcement, and justice reforms following recent spikes in crime and shifts in leadership priorities.

Trump Signs Executive Orders Related to Criminal Justice and Federal Prison Policies

“We’ve had tremendous support,” Trump continued, speaking about the legislation. “To me, it was shocking.”

The law, considered a major set of reforms to the system, aimed to reduce sentencing disparities for drug crimes, incentivize prison rehabilitation programs, and provide opportunities for early release.

But that was seven years ago, a lifetime in politics.

On Monday, Trump — flanked by some of his most loyal second-term cabinet members — once again sat at the Resolute Desk to sign documents related to criminal justice that could put more people in federal prison, rather than releasing them.

One of the executive orders signed Monday mandated that people arrested in Washington, D.C., amid the federalization of the city’s police force, be held in federal prison and charged with federal crimes. Another order set the stage to pressure Washington to bar “cashless bail” for public safety threats, a practice that allows a judge to release people charged with a crime pending a hearing without paying bail.

Increased Federal Enforcement in D.C.

The orders come as Trump has increasingly tasked federal law enforcement agents and national guardsmen with patrolling the streets of the nation’s capital, which he claims is unsafe and overrun by violent crime.

“In D.C. in particular, the objective is holding as many criminal defendants in federal custody and subjecting them to federal charges as possible,” said White House staff secretary Will Scharf, who presented the executive orders to Trump. “That means that they’ll be held pretrial in federal jail, as opposed to just being cut back out on the streets due to a cashless bail policy.”

“We have the room,” Trump replied as he put Sharpie to paper.

According to data published by Washington’s Metropolitan Police, violent crime in the city is down 27 percent compared to this time last year. In particular, homicides have been on a steady decline the past two years following a 20-year high mark in 2023. (The Department of Justice recently launched an investigation into the veracity of the Metropolitan Police Department’s crime statistics.)

Reactions from Advocates and Critics

Some prison reform advocates said the president’s desire for increased police presence and maximum punishment for criminal actions contradicts his past support of constructive pathways out of prison for incarcerated people.

“The President’s attempt to end cash bail risks increasing pretrial detention, which is not a real solution to preventing crime in D.C.,” Alicia Yass, a supervisory policy counsel at the D.C. chapter of the American Civil Liberties Union, said in a press release. The ACLU was a proponent of the First Step Act. “Even short periods of unnecessary detention increase a person’s risk of re-arrest, and cash bail has been associated with a 6 to 9 percent increase in reoffending or committing another crime.”

Others argued that visible law enforcement and the likelihood of being caught dissuade potential criminals, while detention is the first step to rehabilitation.

“The through line I see in the desire from the president is public safety,” said Heather Rice-Minus, president of Prison Fellowship, the largest Christian criminal justice reform nonprofit. “Through prison reform, the goal was how do we use people’s time well to enable them to step into a new way of thinking, a new way of living, so when they come home, they’re not committing new crimes. I don’t think that that is mutually exclusive from [the] belief that crime should be deterred, that crime should be apprehended.”

The Impact of the First Step Act

The First Step Act has directly led to the release of about 51,000 federal inmates and the reduction of more than 4,000 sentences, according to the Bureau of Prisons. Meanwhile, in 2024, the likelihood that someone released from prison because of the First Step Act would return to incarceration was 55 percent lower compared to people who had been released under other circumstances.

Liz Komar, a sentencing reform counsel at The Sentencing Project, called the First Step Act “a wonderful bipartisan achievement that everyone who voted for should be very proud of.”

Historical Context and Political Shifts

Trump, known for his tough-on-crime attitude even before he entered the political arena, had taken some convincing to sign onto the First Step Act. “I started off a little bit on the negative side” of criminal justice reform, Trump admitted at the 2018 bill signing. But after being lobbied by top Republicans like Iowa Senator Chuck Grassley and Lee, plus his son-in-law, Kushner, and celebrities like Kim Kardashian, Trump was swayed.

Much has changed since then.

The murder of George Floyd by a Minneapolis police officer in 2020 sparked a nationwide reckoning about racial bias in the criminal justice system. Following the expiration of COVID-19 stay-at-home orders, violent crime spiked for years in major American cities (though many, including D.C., have seen those rates plummet in 2025). And Trump himself faced a litany of legal issues, eventually becoming a convicted felon before his 2024 election victory.

Brett Tolman, executive director of the conservative criminal justice reform group Right on Crime, said bipartisan support of criminal justice reform was disrupted in 2020 and “both sides bore a lot of responsibility for why the dynamic kind of changed after COVID.”

On the left, he said, “You had this real extremism injected into the criminal justice system, things like defund the police,” and district attorneys refusing to prosecute certain crimes, which was “a disaster of a policy.” While on the right, “The counter-reaction was also extreme,” Tolman said, “you saw conservatives again saying we need longer sentences, tougher sentences.”

Earlier this month, Trump-appointed US Attorney for D.C. Jeanine Pirro sent a letter to the D.C. Council — the legislative branch of the city’s local government — asking that its members reconsider some of Washington’s laws for offenders under 21 that allow sentencing reductions and the disregard of mandatory minimum sentences. Trump has said offenders as young as 14 should be tried as adults for violent crimes.

Komar, of The Sentencing Project, believes those local laws the Trump administration is attempting to repeal are exactly the kind that allow young people a second chance after committing a crime.

“Charging a 14-year-old as an adult makes them more likely to recidivate. I think if we look at what’s unfolding in D.C. right now, it doesn’t make a ton of sense if you understand it through the lens of the First Step Act,” she said. “This is not about public safety. It is about control.”

The White House did not return a request for comment. But, Trump claimed on Monday that more than 1,000 people have been arrested and no murders have occurred in the city since he ordered a federal takeover of D.C.’s police on August 11.

Zack Smith, a senior legal fellow at the conservative Heritage Foundation, backed Trump’s move to temporarily federalize Washington’s law enforcement, and said the intent of the First Step Act was to correct federal prison sentencing guidelines and conditions, mostly for nonviolent crimes, not to arrest people less often.

“In D.C., particularly when it comes to things like juvenile crime, I think there’s a general sense that those juvenile offenders are not being held appropriately accountable when they break the law,” Smith said.