Obama’s Legacy Project

As a federal convict, Jason Hernandez never got a chance to vote for Barack Obama, but for years he dreamed that the President would one day know his name. He had been a high school drug dealer in McKinney, Texas, peddling joints and dime bags before eventually building a criminal operation with his brothers that included methamphetamines and a large amount of crack cocaine. In 1998, at the age of 21, he was sentenced to life in prison without the possibility of parole.

The judge in his case objected to the sentence, but he had no choice. Decades of tough-on-crime laws passed by Congress to target crack made it mandatory. Hernandez’s supplier, who was charged with a similar amount of cocaine but in powder form, received only 12 years. “It’s like living and dying at the same time,” Hernandez wrote from prison in an email about his terminal incarceration. “Imagine being dead with the capability of looking back on your life, wishing you could go back and do so many things different.”

Then, late last year, Obama announced that he would soon set Hernandez free. There wasn’t a lot of fanfare: the White House published the commutations of eight convicted drug dealers in an email to reporters right before Obama left on holiday to Hawaii. In an accompanying statement, the President called his decision “an important first step toward restoring fundamental ideals of justice and fairness.”

In fact, the first step Obama took toward Hernandez’s freedom actually occurred in the Oval Office more than a year before, just weeks after Obama won re-election. The President gathered his senior aides to read out his hopes for a second-term agenda, which he had scribbled on a yellow legal pad. In addition to the stuff that everyone knew about, like immigration reform and jobs, Obama had listed an old priority that had nearly slipped away in the first term: criminal-justice reform.

It was an issue that had animated Obama’s community-organizing days on the South Side of Chicago. It later drove him in the Illinois legislature to push for death-penalty reforms and to pass a law that required police to tape their interrogations in murder cases. And it was an issue he promised to bring to the White House in a 2007 speech that envisioned a “new dawn of justice in America.” “No one has been willing to brave the politics and make it right,” he said at Howard University.

The first term brought no new dawn, burdened as it was by a bitter health care fight and multiple economic and political crises. There were some new programs and reforms at the Justice Department, and a compromise bill that Obama signed reducing the crack-to-powder sentencing disparity to 18 to 1, from 100 to 1. But his pardon-and-commutation record was among the least active of any modern President’s, and he was cautious of appearing to back any government programs that appeared to narrowly target a specific demographic group. “I’m not the President of black America,” he said in 2012, just a few months before his re-election. “I’m the President of the United States of America.”

That caution has now begun to slip away, and a more muscular approach to reforming the federal judicial system is plain to see. Shortly after his yellow-pad meeting, Obama sent an order, by way of the White House counsel, to draw up a list of nonviolent clemency candidates like Hernandez. He encouraged Attorney General Eric Holder to undertake a new sweeping review of the prosecutorial practices that might result in disproportionate sentences. When reporters asked Obama about marijuana, the President no longer just repeated his old lines about not supporting legal weed. He quickly added that something needed to be done about the inequities in punishment for minor drug offenses. “Middle-class kids don’t get locked up for smoking pot, and poor kids do,” he told the New Yorker late last year.

Since Obama’s return from Hawaii, hardly a week has passed without some new announcement of a program or policy push. In late January, the Justice Department issued an open call to America’s defense attorneys to help find more convicts now in federal prison whom Obama might free. Holder gave a speech on Feb. 11 calling on states to restore voting rights to nearly 6 million convicted felons. And in the State of the Union, Obama departed from his past color-blind formulations by announcing a new program specifically to help “young men of color facing tough odds stay on track and reach their full potential.” He calls the initiative My Brother’s Keeper, and it combines more executive actions to keep nonviolent youth out of the justice system with a new partnership with nonprofit foundations and for-profit businesses. “The President is looking on the whole at all the folks in our country who do want to work hard and who do want to play by the rules but just need to be given a chance,” says Valerie Jarrett, one of Obama’s closest advisers.

A bipartisan agreement to reform drug-sentencing laws has also emerged, uniting some of the most liberal and conservative lawmakers in Congress. In late January, a bill sponsored by Tea Party Republican Mike Lee of Utah and Obama ally Dick Durbin of Illinois passed out of the Senate Judiciary Committee on a bipartisan vote of 13 to 5. If passed by the full Congress, it would allow for the judicial reviews of more than 8,000 crack-cocaine sentences in the federal system, cut mandatory minimum requirements and give judges new powers to grant leniency.

The White House and the Justice Department have made clear their eagerness to see the bill pass, cementing Obama’s legacy as the first President in three decades to dial back the punishments for violating federal drug laws. For the first black President, who became a political activist out of college to right the injustices he saw in America’s big cities, the stakes are both more personal and more profound than he tends to let on in major speeches. And his success or failure, by the end of his second term, could help determine his legacy as a champion of the principles he defines himself by. “Every now and again, there is a moment, and this is one of those moments,” Attorney General Holder tells TIME of the recent push. “It is our strong desire to seize this moment.”

The United States of America accounts for about 5% of the world’s population, but its jails hold nearly a quarter of the world’s prisoners. That population has increased by 800% in the past three decades as various waves of crime have ravaged America’s cities. But many of those behind bars have never been charged with an act of violence. As of 2011, 47% of the people incarcerated by states had been convicted of nonviolent drug, property and public-order crimes.

The great lockup has taken its toll. The federal prison system alone costs $6.5 billion a year, and the criminal-justice system that feeds it is rife with racial and economic inequities. Black men have a 32% chance of serving time in prison at some point in their lives, compared with a 17% chance for Hispanic men and a 6% chance for white men. And when they are caught, black men are likely to serve longer sentences–an average of 20% longer than white men for the same crimes, according to one estimate by the U.S. Sentencing Commission. The effect of this sweeping policy of incarceration has distorted many American families and communities. In Florida, 1 in 10 adults doesn’t get a ballot because of past convictions. Among black adults, who tend to vote Democratic, 1 in 13 nationwide doesn’t get a ballot–in some states, including Florida, it’s 1 in 5 .

To date, Obama and Holder have for the most part only tinkered around the edges. A recent academic study suggested Holder’s latest round of prosecutorial guidelines would result in lesser sentences in about 500 drug cases a year, out of a universe of roughly 15,000. And eight commutations is a tiny fraction of the 8,000 or more convicts still serving time under outdated crack laws. But statistics may not be the best measure of reform’s impact. “It’s not a huge deal practically but a huge deal symbolically,” says Ohio State University law professor Douglas Berman, who writes a popular blog on federal sentencing. “It will ripple through not just the federal criminal-justice system but the state criminal-justice systems.”

In the summer of 2013, while they both vacationed on Martha’s Vineyard, Holder remembers warily letting Obama read an upcoming speech he was going to give on Justice Department efforts at reform. In it, Holder declared the longer sentences for black male offenders “shameful” and described a need for a “fundamentally new approach” to crime and punishment. “It’s a gutsy speech,” Holder remembers the President telling him. Yet after the speech was delivered, there was almost no backlash. Groups as disparate as the ACLU and the Cato Institute criticized the Justice Department for not going further.

The pace of reforms can be expected to quicken, which would be welcome news to lifers like Hernandez. For a time, he would spend as many as eight hours a day in the prison law library searching for some error in his sentence that could set him free and sharpening his own petition for commutation. Through the process, he became a go-to person in Oklahoma’s El Reno Federal Correctional Institution for others seeking to file appeals and seek clemency. Since December’s announcements, Hernandez says, there has been a clear shift in how inmates approach the process. “People who thought they were going to die in prison now believe they are not,” Hernandez wrote in an email. “It has turned nonbelievers of the Lord into believers.”

Now 37, Hernandez has been moved to a nearby minimum-security facility and could be released to a halfway house as soon as August. He has a son, 17, whom he has never really known outside of prison visits. One of his brothers was murdered in another prison in 2002 while serving a 30-year sentence, and he has yet to visit his grave. “I always thought if the day ever came I would be screaming for joy, jumping, hollering, singing, dancing. But I didn’t do none of that,” he wrote of his commutation. “There are times I am not able to breathe, or I breathe erratic, my heart races, can’t talk sometimes, can’t think.”

Hernandez has already contacted the Texas narcotics officers who helped put him in jail, offering to meet after his release and possibly volunteer to help dissuade other youth from following his path. “I was just a kid who made a bad decision,” he writes now, “and President Obama agreed by giving me a second chance at life, a decision I will make sure he will never regret.”