'Unlikely coalition': A criminal justice reform advocate sees opportunities in a second Trump term

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. 

"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." 

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.

"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. 

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. 

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."