Kevin Sharp, a retired federal judge who presided in the Middle District of Tennessee, spends a lot of time thinking about the mandatory minimum sentencing laws that forced him to mete out punishments he felt were too harsh. And Sharp's mind often goes right to Chris Young, who he sentenced in 2014 to life in prison.

Young was twice convicted, at ages 18 and 19, in state court on drug charges, the second time for possessing an amount of cocaine weighing about as much as a quarter, Sharp said in an interview.

But in 2010, when Young was 22 years old, he was spotted at a gas station talking to a member of a drug conspiracy. The police said he was making arrangements to buy crack cocaine. And, he was convicted on federal charges.

“If I had been able to use my discretion, this is a seven, eight year sentence, tops,” Sharp said of the case.

But the latest offense was strike three for Young, and, in 2014, Sharp had no choice but to send the then-22 year old to prison for the rest of his life.

“It could not have been more unjust,” Sharp said.

The jurist, since stepping down from the bench last year, has been an outspoken advocate for sentencing reform.

And Sharp, now a name partner at Sanford Heisler Sharp, is not alone in his criticism. He is one of many former federal judges and prosecutors who themselves have previously wielded the threat of harsh mandatory sentences lock down guilty pleas and coax cooperators, and who are now calling on Congress to make changes.

Also among them is John Gleeson, a partner at Debevoise & Plimpton and a retired federal judge from the Eastern District of New York who didn't wait until his 2016 departure from the bench to make his thoughts known on mandatory minimums.

In 2010, for example, Gleeson sparred with the U.S. Attorney's office in Brooklyn over the fate of convicted drug dealer Roberto Vasquez, a small timer in a cocaine dealing operation who faced a mandatory five-year sentence that Gleeson described as “unjust” in a memo explaining his reasoning for Vasquez's sentence.

Gleeson, himself a former hard-charging Eastern District prosecutor who took down mobster John Gotti, asked the government to drop a factor from Vasquez's conspiracy charge that triggers the five-year minimum. The prosecutor on the case, Assistant U.S. Attorney Bonnie Klapper, said she would take it up with her bosses.

A few months later, Klapper, under the eye of a supervisor who was shadowing her, appeared before Gleeson and reported that her office wasn't backing down its position on the five-year minimum for the defendant. 

Klapper explained that Vasquez had already received a “bump down” by pleading guilty to a lesser charge, according to court papers — his original charge carried a ten-year minimum.

“I suppose there is some consolation in the fact that the government did not pursue that absurd course, which would have produced an even more egregious injustice if Vasquez had been convicted,” Gleeson wrote, referring to the prior threat of ten years in prison for Vasquez. “But that hardly explains, let alone justifies, the government's insistence on the injustice at hand.”

The government also argued that the judge had failed to focus on the “seriousness” of Vasquez's prior offenses. After splitting up with his ex-wife, who refused to let Velasquez see his children, he threatened her with a knife in front of the children.

Later, Vasquez violated an order of protection by threatening to kill her.

Despite Vasquez's charges in the drug case, the defendant was trying to get himself on the right track, Gleeson explained. Vasquez developed a stable relationship with someone new, with whom he had daughter and ultimately got engaged. And he kept a steady job as an auto mechanic for a time. But, Vasquez eventually relapsed into cocaine addiction and, to support his expensive habit, sold drugs for his brother.

“The mandatory minimum sentence in this case supplanted any effort to do justice, leaving in its place the heavy wooden club that was explicitly meant only for mid-level managers of drug operations,” Gleeson said.

A Bipartisan Effort

On Capitol Hill, reforming mandatory minimums is one of the rare issue areas that enjoys wide support in both parties and in both chambers of Congress, though not everyone is in lockstep on how much things should change.

In November, the Senate Judiciary Committee unveiled bipartisan legislation, dubbed the “First Step Act,” that would reduce, but not eliminate, mandatory minimums to allow for more judicial discretion, as well as expand the so-called “safety valve” available for nonviolent defendants with little to no criminal history who cooperate with the government and who face mandatory minimum sentences.

The legislation would also retroactively enforce the Fair Sentencing Act of 2010, which leveled out the 100-to-1 disparity in sentencing crimes related to crack-cocaine compared with powder cocaine — a mismatch that tended to favor white defendants over minorities.

The bill has the backing of President Donald Trump, as well as a mixed reaction from law enforcement that includes support from the Fraternal Order of Police but opposition from other groups.

But despite a broad base of support for change, there's good reason to believe that mandatory minimums may remain in place.

Washington has its share of tough-on-crime stalwarts in all three branches of government;

Among them was Jeff Sessions, who recently stepped down from a tenure as U.S. attorney general in which he ordered federal prosecutors to push for maximum penalties, reversing a policy set by former Attorney General Eric Holder of prosecutors declining to charge the quantity necessary to trigger mandatory minimums for nonviolent offenders who worked as low-level drug dealers.  

Holder, now a partner at Covington & Burling in its Washington, D.C. office, issued a statement in May 2017 calling the policy shift  “dumb on crime.” Holder served as a D.C. Superior Court judge from 1988 to 1993, a time when he said he began a “slow evolution” in his thinking about how the criminal justice system deals with drug offenders. He then served four years as the U.S. Attorney for D.C. until joining the Justice Department in 1997.

Alan Vinegrad, Holder's colleague at Covington, has also joined the chorus of voices who say that the federal government needs to rethink mandatory minimums. Vinegrad served as an interim U.S. Attorney for the Eastern District of New York from 2001 to 2002,

“The prevailing wisdom is that more needs to be done,” Vinegrad said.  

In addition to several Republican members of Congress, vocal opponents to changing the status quo include the National Association of Assistant United States Attorneys, which has a membership of 1,500 current and former federal prosecutors, according to its website. 

The group is staunchly opposed to ditching mandatory minimums; Lawrence Leiser, president of the group and adjunct faculty at George Mason University, said that mandatory minimums give prosecutors a powerful tool to fight crime. And with prosecutors across the country fighting against opioids and fentanyl, now is not the time to take it away, he said.  

“I think their heart is in the right place,” Leiser said of lawmakers. “We would like these defendants to not go back and re-victimize.”

Punishing the “low-hanging fruit”

Both mandatory minimums and sentencing guidelines, were enacted in the crack-cocaine-fueled crime wave of the mid-1980s.  

A catalyzing event that led to mandatory minimums was the overdose death of University of Maryland basketball standout Len Bias just days after the 1986 NBA draft.

U.S. Sen. Robert Byrd, a West Virginia Democrat, said at the time that mandatory minimums were intended to decapitate drug rings by bringing strict sentences to kingpins — the “masterminds who really run these operations,” as Byrd put it — and middle managers.

But Congress made a mistake, Gleeson said in his 2010 ruling in the Vasquez case, by tying sentences for drug dealers based on the amount of weight their operations move, not how much heft the accused had in their respective organizations.

Thus, sentences can fall heavily on street-level dealers, the “low-hanging fruit for law enforcement,” Gleeson said.

In the decades since mandatory minimums were enacted, crime rates have fallen across the country, but the ranks of the incarcerated grew substantially. The U.S. Bureau of Prisons reported a headcount of more than 40,300 inmates in its 1985 fiscal year, a number that grew to a high point of almost 219,300 in fiscal 2013.  

The previous requirement that judges use the sentencing guidelines was challenged on the grounds of the Sixth Amendment, which provides the right to a jury trial, In 2005, the Supreme Court ruled that judges are not mandated to give sentences determined by the sentencing guidelines and can use them on an advisory basis, 

But mandatory minimums remain and, unlike sentencing guidelines, there no clear paths of attack in terms of bringing a constitutional challenge to effect change, said Sean Hecker, a name partner and white-collar defense attorney at Kaplan Hecker & Fink who serves as chair of the New York City Bar Association's Task Force on Mass Incarceration.

Thus, efforts to change mandatory minimums are being undertaken as lobbying efforts rather than taking them on through litigation.

“It's ultimately an effort in trying to persuade state legislatures and Congress that mandatory minimums are wildly ineffective in achieving the aims of a criminal justice system,” Hecker said.

Today, about 55 percent of the more than 183,400 inmates in federal prisons were convicted of an offense that carried a mandatory minimum, according to testimony that the National Association of Criminal Defense Lawyers submitted to the U.S. Sentencing Commission in August.

And like many outcomes in the criminal justice system today, mandatory sentences have a disproportionate effect on minorities: almost 63 percent of African-American inmates in the federal system were convicted of an offense with a mandatory minimum sentence, the group testified.

Among those who have done time because of mandatory minimums is Shon Hopwood, who in 1999 was sentenced to more than 12 years in prison for bank robbery and who went on to turn his life around and get a law degree

While he was locked up, Hopwood authored a petition to the U.S. Supreme Court that led to a legal victory for a fellow inmate. He now holds an assistant professor position at Georgetown Law Center.

In the years since Hopwood's release, former U.S. District Judge Richard Kopf for the District of Nebraska, who have Hopwood his sentence, has publicly expressed his regret about the sentence.

“Hopwood proves that my sentencing instincts suck,” Kopf wrote in a blog post.

Since his own experience with the criminal justice system two decades ago, Hopwood said that the American public has come a long way in its understanding in its understanding on criminal justice reform issues, including mandatory minimums.

“Mandatory minimums sounded good, but a one-size-fits-all solution rarely works,” Hopwood said. “The crimes are not committed the same way. The harms are different.”  

As Leiser and other supporters of maintaining mandatory minimums note, the law as it is gives prosecutors a lot of leverage in getting defendants to work with the government — it allows prosecutors to move up the criminal justice “food chain,” Leiser said.

But Sharp, the federal judge from Tennessee, described it differently and used a baseball analogy: it's like taking the power to call balls and strikes away from the umpire and handing it over to the pitcher, he said.

The threat of harsh sentences also tends to encourage some defendants to take guilty pleas instead of seeing their cases through to trial, which could be seen as a way of conserving the resources of the judiciary branch, Hecker said.

But Hecker didn't refer to this cost savings for the federal judiciary in the positive sense; defendants may be frightened by the prospect of lengthy sentences and plead guilty to lesser charges rather than fight to establish their innocence.   

“I think the system would be much fairer if we had more trials and you didn't have the profound risk that exists of folks who are taking guilty pleas to avoid mandatory minimum sentences,” Hecker said.

While reforming mandatory minimums enjoys support from both Democrats and Republicans, some Republicans in Congress have come out in opposition to previous measures to ease sentencing rules.

Leiser said that, if the measure that the Senate Judiciary Committee moves forward, it should include a “spring back” provision to punish offenders who got out of prison early because of a change in the law and went on to commit another crime.

Like other opponents to reforming mandatory minimums, Leiser said his group is concerned that reform efforts could end up jeopardizing public safety.

“You can't just willy-nilly let people out of jail,” Leiser said. “It's deserving of more scrutiny.”

Generally speaking, body politic has in recent years begun to view tough-on-crime policies less favorably. In some locales, like Brooklyn and Philadelphia, district attorneys have been elected to office running on a message of reform rather than the lock-them-up-and-throw-away-the-key approach that was more common for prosecutors decades ago.

But despite shifting public attitudes, Gleeson said that much of the reason that meaningful criminal justice reform has been hard to achieve on the federal level is many politicians still fear being seen as too soft on crime.

“We just can't seem to get there and it's not because there's a really strong well thought-out opposition,” Gleeson said. “It's just kind of ingrained in us.”