President-elect Donald Trump campaigned for president in 2016 in part by styling himself as a tough-on-crime contender who, if elected, would institute a national anti-crime agenda, crack down on immigration and bring "very strong, very swift," law and order. 

His incendiary rhetoric and messaging on crime had set off alarm bells among many Democrats and criminal justice advocates ahead of his January 2017 inauguration. 

"I am the law and order candidate," he told voters, before adding in the next breath, "I am also the candidate of compassion."

But the second part of his remarks did little to assuage fears that under Trump, the U.S. would see an indiscriminate crackdown on crime. 

Jessica Jackson, a human rights attorney and CEO of criminal justice advocacy group REFORM Alliance, told Fox News Digital that she originally had some reservations of her own.

"First and foremost, I'm a Democrat," Jackson said in an interview.  "So, to work with President Trump back in 2018 was considered a little bit unusual." 

But Jackson did just that, lobbying for the First Step Act, a bipartisan bill aimed at reducing federal prison populations through curbing disproportionate sentences, promoting rehabilitation and allowing certain inmates the possibility of early release. 

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Jackson was part of a large group of police groups, religious leaders, prosecutors and celebrities who lobbied on behalf of the First Step Act. 

Their efforts were successful, and in December 2018 Trump signed the First Step Act into law.

The law has been roundly praised for both helping to reduce the federal prison population and, importantly, cutting down the rates of recidivism—the rate of formerly incarcerated persons who re-offend.

Jackson noted that the law has resulted in a reduction of recidivism "from about 49% to 9.7%." A 2024 report from the Brennan Center for Justice estimates a slightly lower, but still striking, reduction rate of 46.2% to 9.7% of recidivism among former inmates aided by the First Step Act.

"I think the biggest lesson that I learned in the first administration was if you engage with the administration, there are opportunities to make progress on the issues that you care about," Jackson said of working with Trump.

Now, she and other criminal justice advocates see more opportunities to work together in Trump's second term. 

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One major opportunity that Jackson sees for Trump is passing the Safer Supervision Act, bipartisan legislation aimed at helping formerly incarcerated persons transition back into their communities. Proponents see the bill as a way to build on the success of the 2018 legislation.

Former inmates overwhelmingly struggle to readjust to life after prison, and the Safer Supervision Act seeks both to aid in employment opportunities for former inmates and to reduce the litany of burdensome parole and probation requirements.

It looks to address major hurdles faced by ex-cons, including a lack of structure, trouble finding a job and the many gaps in the federal parole and probation system, which is itself made up of understaffed and underfunded programs.

These hurdles have, at times, landed ex-cons behind bars for what appear to be largely innocuous reasons—ranging from missing a meeting with a parole officer to leaving a judicial district without permission or associating with people who have former convictions or are engaged in criminal behavior. At times, it is not communicated to the ex-prisoner what exactly the restrictions are. 

Jackson said that her team once worked with a former inmate who had traveled to and from work on public transit, eventually saving up enough money to make a down payment on a car.

Unfortunately, when he went to finance the car, she said, "It turns out that unbeknownst to him, and buried in the list of onerous conditions, was that he couldn't open a bank account without talking to a supervision officer."

"So, here’s a guy who thinks he's doing something great—getting a car to go back and forth to work; taking his kids to school. And the next thing you know, he's got a violation of his supervision and is being sent back in," Jackson said. 

As a whole, former inmates are highly prone to recidivism: A 2023 Justice Department analysis of prisons in 24 states found that a whopping 82% of people released were rearrested at least once in the 10 years following their release. (A still-significant 43% were rearrested within a single year.)

Jackson hopes that Trump will make good in his second term on expanding these criminal justice reform initiatives—by passing the Safer Supervision Act and implementing other measures, such as second-chance hiring. 

Asked whether she had been in talks with any transition team staffers, Jackson laughed. "It's funny, because everybody keeps asking me like, ‘Well, have you talked to anybody over there?’"

"We came together in a very unlikely coalition, and we were able to make real progress—we never actually stopped talking to them," she said.

"And I think we're excited about the opportunity to continue those conversations and to make progress where we can."