Wayland Wilson could have been out a quarter-century earlier if he had pleaded guilty.

“I couldn’t plead to something I didn’t do,” he said. “That’s why we ended up going to trial.”

It was 1993, and the drug war catalyzed by Ronald Reagan in the 80s was in full swing. The nation was in hysterics about the threat of crack cocaine, and politicians of all stripes were running on a platform of “tough on crime”.

Wilson, a husband and a father of two, was implicated in a crack-related drug conspiracy on a tip from an informant bargaining with prosecutors for less time. He was pressured to take a plea deal that could have gotten him out in 11 years, but he elected to take his chances. A mostly white jury convicted Wilson, a black man, on all charges. Thanks largely to federal mandatory minimum sentencing, Wilson, a first-time nonviolent offender, was given 37 years. “I had never even had a parking ticket. Now they had me locked in highly secure facilities,” Wilson said.

This May, more than two decades into his sentence, Wilson became one of the lucky ones. He was one of 58 federal prisoners granted an early release by Barack Obama as part of a pronounced late-presidency focus on criminal justice reform.

“It really touches you to have the commander-in-chief reach down and correct what was wrong,” Wilson said. “And yet, people still don’t want to see that it was a mistake to lock people up and throw away the key for a nonviolent crime.”

Obama’s presidency has taken place in an era of unprecedented national attention on the inefficiencies and inequities of the US criminal justice system. From pop culture phenomena such as Orange is the New Black to political movements such as Black Lives Matter, issues largely ignored by the public for decades have moved dramatically to the fore, and support for reform has begun to engender rare bipartisan support.



On the surface, Obama’s legacy appears to reflect this shifting zeitgeist. He was the first sitting president to visit a federal corrections facility, the first president to oversee a sustained reduction in the incarceration rate in a half century, and has issued clemency to nearly 1,000 inmates over his time in office, more than his last three predecessors combined.

Criminal justice reforms under Obama

Commuted the sentences of a record number of federal prisoners (EA) Made it illegal for most federal agencies to ask job applicants if they have been convicted of a crime (EO) Ended the practice of placing federal juvenile prisoners in solitary confinement (EO) Reduced the crack cocaine/powder cocaine sentencing disparity (L)

Launched more civil rights investigations into police departments than the previous two administrations combined (DOJ) Began phasing out use of private prisons for federal inmates (DOJ) Launched a variety of initiatives promoting community policing and alternatives to incarceration (WH) Launched a pilot program to track police use of force nationwide (DOJ) Commissioned a task force on policing reform (WH)

But even as the Obama administration has looked to address criminal justice policy at all levels, from policing and prosecution to sentencing, incarceration and re-entry, the US remains an extreme outlier among the world’s developed countries. On matters of police violence, incarceration and draconian punishment for nonviolent crimes, the country remains unmatched.



And now, as the nation prepares for President Donald Trump, who ran a campaign openly hostile to the prospect of progressive criminal justice reform, there’s ample reason to fear that whatever progress has been made could be lost in the blink of an eye.

A nation of second chances?

In his second term, Obama hasn’t been shy about using his executive power to push some limited reforms around the mostly gridlocked US Congress. Through his Department of Justice and the use of executive orders, Obama has made moves on reducing the use of solitary confinement, phasing out private prisons and scaling back federal drug prosecutions.

But because Obama had to work around Congress, much of this work could be easily reversed or abandoned. .

For the most part, Trump’s plans for criminal justice remain opaque. He did not make the matter a major campaign issue, aside from making vague promises to be a “law and order candidate”, but has been critical of several of Obama’s initiatives, specifically his embrace of clemency for long-serving nonviolent drug offenders.

“We don’t know what it’s going to mean, but the likelihood is we’re in a much worse place,” said Phillip Atiba Goff, president and co-founder of the Center for Policing Equity.

Jessica Jackson-Sloan, the national director for #cut50 – an advocacy group which seeks to cut the US prison population by 50% over the next 10 years – said part of the impact Obama’s actions have is reminding people just how little power the president has to draw down mass incarceration.

“He can commute sentences but he cannot change the laws on the books,” Jackson-Sloan said. ”The president and the DoJ can do quite a bit, but Congress really holds the keys to this car.”

Indeed, if there is one theme that unites nearly all of Obama’s steps towards reform on criminal justice, it’s the limited reach of nearly all his initiatives. Virtually every step the administration has taken either exclusively applies to federal prosecutions and inmates – a small fraction of cases nationwide – or came in the form of non-binding suggestions and support, like the recommendations and resources provided by his taskforce on 21st century policing in 2015. That’s because most of the criminal justice system lies far outside of presidential authority, in the hands of 50 states, 18,000 law enforcement departments and tens of thousands more local judicial jurisdictions.

“If, for example, the president were to let go of every federal prisoner – and that’s not smart criminal justice reform in all likelihood – he’d be handling just 1/11th of the total number of people who are incarcerated,” Goff said. “This is not and cannot be a federal problem only, but what the president has provided is leadership. He’s said, here’s a model you can follow, and he deserves credit for that.”

Fixing a broken system

For much of Obama’s first six years, criminal justice remained largely out of the spotlight. The president campaigned broadly on some generic reforms, like prison work and education programs, but expended most of his political capital on other priorities such as passing and defending the Affordable Care Act.

“Criminal justice reform was treacherous waters in the first term,” said Van Jones, who served in the Obama administration in 2009 and went on to co-found #cut50. “Pre-Trayvon [Martin] and Black Lives Matter, these issues were considered to be ultra-liberal and African American.”

Obama was, according to Jones, maintaining hope that he could build bridges across race and party under his presidency and “did not want to be seen as excessively black or liberal in his agenda”.

But ultimately, “the African American community got more insistent in its claims, and the Republicans got more reasonable in their own critique and set of concerns about criminal justice”, Jones said, opening the door to more direct engagement from the president.

In July 2015, in front of an NAACP convention audience in Philadelphia, Obama delivered his first major speech focused on criminal justice reform. “Mass incarceration makes our country worse off, and we need to do something about it,” Obama said, as he noted the bipartisan support for reform and put forward some his plans for the rest of his term, such as the aggressive use of commutations.

The president’s administration also found plenty of less visible ways to tinker around the edges of mass incarceration. In 2010, Obama made good on a campaign promise to reduce the 100-to-1 sentencing disparity between crack and powder cocaine. This relic of the “crack boom” is one that had been maligned by activists as racist for decades. Since Obama lobbied for and signed the bill, federal prosecution of crack offenders has been cut in half. This mirrors drops in drug prosecution across the board after Holder’s DoJ announced “smart on crime” reforms in 2013 that expanded so-called compassionate release, and guided prosecutors away from seeking maximum punishments for smaller-scale drug crimes.

Through executive orders, Obama has also ended the practice of placing federal juvenile prisoners in solitary confinement and made it illegal for most federal agencies to ask job applicants if they have been convicted of a crime, part of a broader movement known as “ban the box”.

The president commissioned the 21st Century Task Force on Policing in the wake of unrest in Ferguson, Missouri, and followed up by hosting more than one roundtable bringing together activists and law enforcement officials in an effort to try and bridge divides between the two.

His White House has also promoted collaborative programs such as the Data-Driven Justice Initiative, which encourages cities, towns and counties to share strategies for cutting unnecessary arrests and holding fewer suspects pre-trial when they do not pose a threat to public safety.

A city like a powder keg

In 2014 the high-profile police killings of several unarmed black Americans led to wholesale changes in the national consciousness on the nexus between race and policing. And nowhere was this more true than the death of Michael Brown in Ferguson and the enduring days of protest and unrest.

In the aftermath, The Obama-Holder DoJ produced two sets of investigative findings. The first broadly refuted many of the lingering accusations about what transpired that August day between Ferguson police officer Darren Wilson and the 18-year-old Brown, including whether his hands were up in surrender.

But the second report, which focused on the police department as a whole, took the unprecedented step of delving into the ways the department was operating as a de facto revenue agency for the municipal government. “Ferguson’s law enforcement practices are shaped by the City’s focus on revenue rather than by public safety needs,” the report read, adding that the city’s “police and municipal court practices both reflect and exacerbate existing racial bias”, including a reliance on racial stereotypes.

“That’s the exact right level of analysis to get into,” said Goff. “If you compare that to anything the civil rights division did in the prior administration, they are from different planets.”



The law that gives the department the authority to conduct broad, sweeping analysis like what was done in Ferguson traces to another flashpoint moment of police violence in the nation’s history: the 1991 LAPD beating of Rodney King. The following year, a statute was added to the federal books giving the DoJ the authority to obtain “relief to eliminate the pattern or practice” of civil rights violations by law enforcement agencies.

But power was used sparingly until Obama deployed it to make “federal engagement around civil rights issues involving policing more robust”, Smith said. Under Obama’s justice department these “patterns and practices” interventions increased more than 50% over the Clinton and Bush years. Obama’s administration used these investigations to impose federal oversight on eight large police departments over its two terms. In their 16 years combined, Clinton and Bush oversaw just six.

“There was a moribund civil rights division that was rejuvenated like Lazarus when Obama took office in 2009,” Goff said.

Jones said this reborn civil rights division had served a crucial role during a period in which frustration with the system had boiled over in cities and towns across the country.

“Even where there hasn’t been redress, it’s at least been addressed,” Jones said. “The quickness with which the DoJ has said ‘we’re going to investigate’ – it signaled to people that there’s somebody in DC who believes that their concerns were worthy of real attention.”

Irreversible action

The president’s most direct contribution to the rolling back of mass incarceration has been his aggressive use of the executive power to grant clemency to federal prisoners, especially during his final year in office. More than 700 of the 1,014 pardons and commutations granted under Obama, including Wilson’s, have come in the past 10 months.

The spike follows the DoJ’s 2014 clemency initiative, which encouraged federal prisoners meeting certain criteria to submit petitions for commutations. As a result, the department has processed more than 20,000 petitions over these past three years. By comparison, during Ronald Reagan’s entire eight years in office, his justice department processed just over 1,300 applications and granted a total of 13.

But while the number of accepted petitions under Obama is unprecedented, it is also underwhelming, in part because the federal government has not been able to keep pace with the tens of thousands of applications.

While most of Obama’s executive actions could be undone by Trump, cutting short the sentences of inmates like Wayland Wilson will have a permanent impact for those people.

“My big hope is that this clemency campaign now really breaks through in Obama’s final days,” Jones said. “That’s the last thing he can do to really cement his legacy: send home folks who have served more than a fair amount of time and let them return to their families.”

