The Quality of Mercy

From Our March/April Issue

The Quality of Mercy

An evangelical Christian and former prosecutor, Mark Osler has become one of the country’s most effective advocates for criminal-justice reform. 

April 7, 2014

On a Sunday in September, a few minutes before the 10 A.M. worship service, Mark Osler stands in the lobby of the First Covenant Church in downtown Minneapolis. He’s just been fitted with a pencil-thin, flesh-colored microphone, the kind that pop stars wear so they can dance while belting out lyrics. Fifty-one years old and of average build, Osler is the opposite of imposing. As usual, his wiry hair is a mess. A strand flops over his forehead, giving him a slightly boyish air. With his mouth set in a straight line and his thick eyebrows knitted together, his expression tends to be serious or, if he’s lost in thought, dour. “I look like Britney Spears,” he says, a bit doubtful about the microphone.

First Covenant is one of the largest churches in Minneapolis. Built in 1887, it was originally known as the Swedish Tabernacle, named after the evangelical immigrants who constructed the three-story redbrick sanctuary. Reflecting the city’s demographic change, First Covenant has moved away from its roots. There’s Bible study in Spanish, “holy yoga” on Sunday, and an 11:30 A.M. Ethiopian service. The church works with other congregations, including a synagogue and a mosque, to address Minneapolis’s homeless problem. The worshippers this Sunday are white, black, Latino, Hmong, young and old. As they sing the first praise songs of the service, some hold out their palms. A giant screen displays the lyrics, most of which can’t be found in an old-fashioned hymnal. Even the version of “Amazing Grace” has additional verses sung to a different melody.

Dan Collison, First Covenant’s pastor, has invited Osler to speak about Christianity and justice. A professor at the University of St. Thomas School of Law, a Catholic institution located a mile away, Osler is one of the country’s leading advocates for reforming the criminal-justice system. Over the past ten years, he’s fought to dismantle the mandatory drug sentences that have left tens of thousands of black men in prison for decades. More recently, he’s called for pardons and commuted sentences. He’s won in the Supreme Court and lobbied on Capitol Hill and in the White House.

A former U.S. attorney, who prosecuted some of those black men, Osler can claim credibility on these issues. But what has made him particularly effective is that his efforts are rooted in his identity as a Christian. Although not well known in progressive Christian circles, Osler has emerged as one of the most eloquent spokespeople for what in the late 19th and early 20th centuries was commonly referred to as the “social gospel”—merging the precepts of Protestantism with the principles of social justice.

“I would rank him up there with the quiet heroes of the civil-rights movement of the ’60s, as a person who’s taken his values of faith and applied them to progressive ideals,” says Chet Edwards, a former Democratic congressman from Texas, whom Osler lobbied but didn’t always win over.

Osler prefers speaking at conservative or evangelical churches like Covenant. It offers a chance, he says, to engage people who view the world differently than he does. He’s delivering two more sermons in the next four weeks—at the Church of the Holy Comforter in Richmond, Virginia, and at St. Mary’s Episcopal in Anchorage, Alaska.

At the conclusion of the first set of music, Collison welcomes the congregants. He reminds people about upcoming meetings, introduces a skit, and conducts a brief Q&A with Osler. By the time Osler gets up to talk, an hour has passed, and the congregation is restless. He begins, as he invariably does, with the week’s reading from the lectionary. This week, it’s Luke 6.

“Blessed are you who are poor, for yours is the kingdom of God. Blessed are you who hunger now, for you will be satisfied. Blessed are you who weep now, for you will laugh,” Osler reads before getting to the less frequently cited sentences. “But woe to you who are rich, for you have already received your comfort. Woe to you who laugh now, for you will mourn. Woe to you when all men speak well of you, for that is how their ancestors treated the false prophets.”

Osler pauses. “Sometimes,” he says with a grin, “the Bible is not very reassuring for a fairly affluent straight white guy from Edina,” referring to the Minneapolis suburb where he and his family live. “But that is me, and this is one of those times. In this passage, Jesus is talking about turning everything—everything—upside down. The poor will have the kingdom, while the rich will face woe. The hungry will be filled, while those who are full will be hungry. Those who are reviled will be blessed, and it’s bad when all speak well of you. This teaching, this idea of turning everything upside down, is dangerous.”

No theatrics inform the sermon. Osler doesn’t pace and only occasionally gesticulates. He speaks methodically and conversationally, as if the congregation were a jury he has to persuade. “At the very least,” he continues, “when Jesus tells us the world should be upside down from where it is today—‘woe to you who are rich’—at the very least it means we have to ally ourselves with the poor, with the hungry, with the reviled. That’s our team. That’s the side that, as Christians, we’re on, we’re assigned to.”

In five minutes, Osler has done what he likes best—reveal the radical, challenging side of Christianity. He has identified himself as “someone from the pews.” But Covenant isn’t his church, and he doesn’t fully fit in here. He also doesn’t quite fit in at St. Stephen’s Episcopal church, where he currently worships, nor did he quite fit in at the Baptist church he attended when he taught law at Baylor University and lived in Waco, Texas. It’s unlikely he was a perfect match for the Congregational church he was raised in or the Quaker meetings he sometimes joined when he was in his twenties. A progressive among evangelical Christians and an evangelical Christian among progressives, Osler has spent much of his life subverting expectations.

Osler pulls out a copy of Ernest J. Gaines’s 1993 novel A Lesson before Dying. He outlines the basic plot, which centers on a schoolteacher in a small black town in 1940s Louisiana, who counsels a man on death row. During this time, the boxer Joe Louis was a hero to black Americans. Osler reads a passage: “As vividly as if I were there, I had seen that cell, heard that boy crying while being dragged to that chair, ‘Please, Joe Louis, help me. Please help me. Help me.’”

Putting the book down, Osler says, “I get letters that cry out like that. Every week. They’re from people who want my students and me to seek clemency for them—desperate men and women serving life terms very often. And they come with carefully handwritten return addresses from those places we warehouse men and women in this country.

“Inside each one, painstakingly written, is a story. And it’s always a tragic story. They think I’ll know a way to get them out of prison after 25 or 30 or 37 years for a narcotics case that almost no one remembers. In the end, probably writing to me is as hopeless as writing to Joe Louis. But I can’t throw the letters away. I have to try to do something. And so I do. I try to get the law to change. I try to get the president of the United States to try to take seriously his constitutional duty of showing mercy with the pardon power. I try sometimes to work with my students to save just one of them.”

The squirming and occasional cough that could be heard early in the sermon have ceased. Some members have their eyes closed. Others look around with concern.

“Because the people who write those letters,” Osler goes on, “are Jesus. Because he said, ‘When you visit those in prison, you visit me.’ He didn’t say, ‘When you visit the innocent person in prison,’ or ‘When you visit the political prisoner.’ ‘When you visit those in prison,’ and these are the people in prison. They are Jesus. And their mothers who write to me and beg that we help their child so that she can see him again before he dies—they are Mary. Dutiful. Heartbroken. Watching their child die.”

There it is: the message Osler has spent years delivering—that mercy has been stripped from Christianity and society and must be restored.

“So we do have to seek social justice, as hard as it is—and it is hard,” he says. “To ally ourselves with the hungry, with the reviled, we have to make ourselves vulnerable. And that’s a hard thing to do. We have to open ourselves up to do things we don’t usually do. That’s part of the deal: that it won’t be safe or painless."

Dan Epstein

Federal defender Andrew Densemo's speech in court against mandatory sentences pushed Osler to rethink his views. 

Until he was six years old, Osler grew up in a middle-class neighborhood on the east side of Detroit. His mother, trained as a bacteriologist, stayed at home to raise Osler and his two younger siblings. His father worked in sales at a commercial photography studio. Osler’s first memory is of running into the street after being kept in for days, smelling gasoline, and seeing a National Guardsman near his home, before his mother scooped him up. The 1967 Detroit riots, he says, “are why I take criminal law so seriously.”

Within two years, the Oslers moved to Grosse Pointe. It was a chance to buy a house by a lake in a suburb with a highly touted school system. The family wasn’t religious. So Osler’s parents were taken aback when his kindergarten teacher suggested they might want to consider some sort of church for their son. “He’s always talking about God,” she explained.

His parents eventually chose Grosse Pointe United Church (it has since changed its name), which was affiliated with Congregationalists, a Protestant denomination with a long history in New England. According to Osler, the church was moderate for Grosse Pointe but conservative for the country. After his confirmation at 16, Osler told his minister he wanted a full-immersion baptism. “No one in my church had ever done that,” he says. “It was not something Congregationalists do.” The minister complied, conducting the ceremony in a Baptist church. “It was,” Osler says, “something I was proud of at the time.”

Osler attended the College of William and Mary, in Williamsburg, Virginia, where he majored in history with a government minor and gained a reputation as smart and independent. He moved back to Detroit after he graduated, finding work as a florist’s delivery boy. Looking to supplement his income, he answered a newspaper ad for “a young, resourceful person.” Osler had landed his first job in law—as a processor. Sometimes he’d bring a bouquet to fool people into thinking he was delivering flowers instead of serving them with legal documents.

In 1987, he entered Yale Law School. “Suddenly I’m around the smartest people in the world, it felt like,” he says. “It was like an intellectual vacation.” One of his mentors was Daniel Freed, perhaps the country’s leading authority on sentencing. Osler thrived at Yale, and in his third year, he was named a senior editor at the law review. He also started regularly attending Quaker meetings. “I just really loved the practice of silence,” he says. “I liked the idea of faith being as much about questions as it was about answers.” The year after graduation, he clerked for U.S. District Court Judge Jan DuBois in Philadelphia, where he continued going to meetings. When he married three years later, he did so in a Quaker service.

By then Osler had returned to Detroit, where he was a junior associate at Dykema Gossett, the city’s biggest law firm. His goal was to become a federal prosecutor, and in 1995, the Clinton administration named him an assistant U.S. attorney for Eastern Michigan. The job revolved around putting away crack dealers.

Osler had seen crack ravage Detroit, a city he loves. “It’s being in love with someone who breaks your heart the same way over and over,” he says. “You think it can’t get worse, and then it does.” Bleeding jobs, its population shrinking, Detroit experienced a dramatic rise in violent crime in the 1980s. “I was really a believer,” he says. “Crack’s a serious problem—you’ve got to do something about it, and this seemed like something.”

Crack didn’t exist until the mid-1970s, when a street chemist, now lost to history, discovered that mixing cocaine with baking soda and cooking it yielded small rocks that could be melted and smoked. Drug dealers had been trying to find a way to offer smokable cocaine, which would provide a higher high for a shorter duration. From an entrepreneur’s point of view, the “baking-soda method” was a brilliant stroke: It required no skill and made the drug cheaper. A glut of cocaine from South America and the Caribbean in the early 1980s further drove down prices. By the end of 1985, you could find crack in most major cities.

The stereotype came quickly: This was a black drug. Racial anxieties added to the specter of crack addicts being especially dangerous. A study of 23 infants spawned extensive coverage of “crack babies,” who, it was claimed, would be permanently disabled and require a slew of services for life. The message was “this was the most horrific drug ever,” says Nkechi Taifa, a senior policy analyst on civil and criminal-justice reform at the Open Society Foundations. “It was a bad drug, don’t get me wrong. But all of that was hyper blown out of proportion.”

The hysteria peaked in 1986 with the death of University of Maryland basketball star Len Bias, who overdosed two days after being drafted by the Boston Celtics. Although he likely died from snorting cocaine, many presumed that, because he was black, crack was the cause. Within a few months, Congress had passed the Anti-Drug Abuse Act, which created mandatory minimum sentences for crack and treated one gram of crack as the equivalent of 100 grams of powder cocaine.

The new law was part of a wave of “tough on crime” legislation. Daniel Freed, Osler’s mentor at Yale, had spent years calling attention to the radical and unjust disparities in federal sentencing. In 1984, drawing on Freed’s work, Congress passed a set of mandatory minimum sentences for certain crimes, making them statute, and established a commission to institute sentencing guidelines. Intended to prevent extreme variations in punishments for the same crime, the new system offered judges a massive grid that incorporated multiple variables to consider when sentencing. A person could be found guilty of drug dealing, for instance, but the presence of a gun would bump up the mandatory sentence; the presence of a gun and a prior conviction would bump it up even more.

In 1988, Congress singled out crack as the only drug with a five-year minimum jail sentence for possession. For the next ten years, Congress continually made mandatory sentences harsher. Democrats were as hard-line on crack as Republicans. When, in 1995, the U.S. Sentencing Commission proposed guidelines stipulating that crimes involving crack and powder cocaine be treated equally, Congress passed a law overruling the recommendation, which President Bill Clinton signed.

Freed came to oppose the new structure. “Discretionary actors, including judges, prosecutors, defense attorneys, and probation officers, find themselves torn between allegiance to rigid rules and an urge to do justice in individual cases,” he wrote in 1992, warning that the new guidelines might soon “lose all credibility.”

One of the consequences of mandatory crack sentencing was that it gave prosecutors an enormous amount of power. Once a prosecutor determined the charges, defendants, the vast majority of whom were black and poor, had few options. The choice they faced was often between a lengthy prison term from a plea bargain or the prospect of an even lengthier prison term from a trial. Because sentences were mandatory, judges had little discretion once a verdict came in.

“Being a prosecutor in Detroit in the late ’90s was about bullying drug defendants to try to get to their bosses,” says Douglas Berman, a law professor at Ohio State University, who would later become one of Osler’s closest allies in reforming drug-sentencing laws.

“That doesn’t seem like much fun if you’re virtuous. It’s only fun if you like being a bully.”

Ohio State University Moritz College of Law

Ohio State law professor Douglas Berman oversees a journal and blog at the heart of the criminal-justice reform effort. 

Andrew Densemo, a federal defender who worked in Detroit courts at the same time as Osler, remembers a client who was tried for intent to distribute marijuana and cocaine. The prosecution offered ten years in federal prison. “I told the prosecutor, ‘You can kiss my ass. I don’t plea for ten years,’” Densemo says. “We went to trial and the client got 15. Looking back, I would have taken those ten years.”

Prosecutors wanted to scare defendants into giving up information about major dealers in exchange for a lighter sentence. But few low-level dealers had much information, and those who did rarely snitched for fear of repercussions. Instead, defendants often named other low-level dealers, and they usually exaggerated, making the crimes sound as bad as possible so that they could have a shot at a better deal.

Prosecuting, Osler says, took its toll. “Levels of tragedy piled one on top of another,” he says. “I’d hear one of those stories and think, how can there be a creator who would let this happen to his creations? Where’s the god that gives a damn?”

At 32 years old, Osler was living in Grosse Pointe, not far from his childhood home. He and his wife had started a family and attended the same Congregational church where he’d been baptized 16 years earlier. For five years, he drove nine miles to his office in Detroit’s federal courthouse, where every day he tried crack cases—in the end, hundreds of crack cases. “He was a nice guy, who did what he was supposed to do,” Densemo says. “He was told to lock people up, and he locked people up. He did it very well.”

Sometimes, Osler would arrive at a sentencing hearing without any preparation. The defendant’s fate had been sealed when Osler had decided which crime to charge him with. The cases bled together so much that for years afterward, he misidentified the case that changed his life.

He likely walked up the seven steps of the imposing, block-long courthouse carrying the minimum amount of paperwork. The defendant was likely a young, poor black man who had spent his life in Detroit and was likely guilty of using or dealing crack. Osler would have risen from his chair and told the judge he wanted the mandatory minimum. Then Andrew Densemo would have given his speech.

Osler has referred to the case on numerous occasions. He calls it the “futile speech” story. The heart of the story he tells is the trial of Anthony “Bull” Sheppard, a teenager arrested with a little more than four grams of crack and for possession of a gun, with Judge Anna Diggs Taylor presiding. As it turns out, Densemo never defended Sheppard. Perhaps this doesn’t matter, because during this time Densemo nearly always gave the same speech, and Osler’s memory of what he said is accurate, even if the specifics of the case are not.

Densemo, Osler remembers, made “a passionate 20-minute argument against the imposition of the mandatory minimums. He described the way it affected the black community, the failure of the law to stop crack trafficking, the unfairness of locking up this teenager for a longer period than the bank robber Judge Taylor had just sentenced, and the absurdity that crack was punished so much more harshly than powder cocaine, from which crack was made.”

The speech had no immediate effect. The defendant—whoever he was—went to prison, and Osler went back to his office. But he recalled the speech as he tried more cases, and he remembered it after he left the U.S. attorney’s office in 2000 to teach at Baylor Law School.

Densemo would continue to give the speech at sentencing hearings for another decade. He, too, no longer recalls which case was which or in which of his cases he went up against Osler. “They were all the same,” he says. “The numbers were the same. The defendants were the same. I had argued against that law so many damn times. It all merges.”

And the intention, Densemo says, was always the same. “The goal was to get those in power to realize that these sentences were wrong—that they were hurting citizens, they were hurting the society. That was my main goal. To just add my voice to all those saying change the law. The hope was that someone on the Court of Appeals would see it. Some prosecutor, some judge—somebody. That it would strike a chord with somebody and somebody, who had more power than I, would say, ‘Hey, maybe we do need to change that law.’ Eventually it did happen, thank God.”


Waco, Texas, a city of 125,000, contains more than 200 Baptist churches. Families say grace when their meals arrive at Cheddar’s, and “God bless” substitutes for “goodbye.” Located a few blocks from downtown, Baylor University is the largest Baptist school in the country with more than 15,000 students. Alcohol is forbidden at events, dormitories are single-sex, and almost all professors are practicing Christians.

In 1999, when Osler decided to leave the U.S. attorney’s office and teach law, Baylor was one of two schools interested in hiring him. During the second-round interview, the president and provost discussed his religious leanings with him. In retrospect, he says, the conversation gave a “pretty foundational impression of what Baylor is like. People are going to ask you, ‘How is what you’re doing influenced by your faith?’” Baylor was Southern and conservative and offered an ideal community for Osler to explore the connections between his Christian beliefs and his love for the law.

Soon after arriving, Osler joined Seventh and James Baptist Church. By Waco standards, the church was moderate. The congregation included a number of Baylor professors, and members were encouraged to give classes on a wide range of subjects in a Chautauqua-like setting. With adult Sunday school, prayer breakfasts, and services on Wednesday nights as well as on Sunday, the church was more fervent than Grosse Pointe United. The Mark Osler who at 16 had insisted on an immersion baptism had found what locals call a new church home.

A year after joining Seventh and James, he proposed that he stage the trial of Christ, with himself as prosecutor and members of the congregation as the jury.

Thomas Whisenand / University of St. Thomas

Osler argues that Jesus should receive the death penalty in his staging of the trial of Christ. 

Osler had arrived at the idea one Sunday when he read about a death-row inmate’s last meal. While taking the communion wafer, Osler says, he realized that the Last Supper represented the last meal of a condemned man.

“I was a prosecutor for five years, attending church the entire time, and I never contemplated that my vocation and faith had a strange and strong narrative link,” Osler writes in Jesus on Death Row, a book he later wrote about restaging the trial. “The fact that God’s son came to earth as a man subjected to capital punishment seems to reveal God’s intent that we care about not only that man but also that process.” Osler designed the trial and discussion, which stretched out over four Sundays, to show how the legal issues that drove Jesus’s trial still had bearing. But his purpose was more provocative. Texas conducted more executions than any other state, and he wanted to ask his congregation why Christians, especially Christian Texans, supported capital punishment.

From the first, Osler was a popular teacher. He created a course with two ministers on the similarities between advocating in court and giving sermons. His classes were packed and, according to his research assistant, Dustin Benham, “he was beloved. You wanted Mark to be satisfied, and you wanted to be like Mark.”

In 2003, Osler received a call out of the blue from Graham Boyd, who was then director of the American Civil Liberties Union’s Drug Law Reform Project. Boyd had been brought into a case in nearby Hearne, Texas, where 28 residents, all but one of whom was black, had been arrested in a drug sweep. An informant, who later recanted, had given the names of supposed drug dealers. Rather than investigate the allegations, the county prosecutor charged everyone, threatening them with decades-long prison sentences unless they accepted plea deals. When the cases went to trial, all were dismissed but the seven whose defendants had agreed to the pleas.

Boyd had called Osler for help on a civil suit on behalf of the defendants against county officials, because he needed local counsel—someone who looked and sounded like a Texan and wouldn’t alienate the Waco court. “I was as much of a Yankee as Graham Boyd,” Osler says. But he knew whom to call: David Moore. Although born in Louisiana, Moore is about as Texan as they come. “I don’t own a pair of shoes,” Moore likes to say. “All I’ve ever worn are cowboy boots.” Moore, Boyd, and Osler made a formidable team, and the county eventually settled (the terms were not disclosed).

For Osler, the Hearne case was the first time he worked closely with people accused of dealing drugs. “It was huge,” he says, “to see someone who’d been arrested in what was basically a racially motivated jam-up.” Almost from the moment he had arrived at Baylor, Osler had begun to examine the doubts that had been brewing since hearing Densemo’s speech. He did this mostly by writing and lecturing about the war on drugs and mandatory sentencing, arguing initially that the guidelines needed to be revamped. Like most everyone else, he didn’t think it was possible to eliminate mandatory sentencing. “I should have had a broader imagination,” he says.

Filing briefs on behalf of the ACLU and others, Osler joined the effort to reform the sentencing guidelines at a critical juncture. Around the time he was helping on the Hearne case, the U.S. Supreme Court started to weigh in. In 2004, the Court took up Blakely v. Washington. The case concerned a man named Ralph Howard Blakely accused of kidnapping his wife. Blakely negotiated a plea deal for second-degree kidnapping, which, according to Washington state’s guidelines, required a prison term of between 49 and 53 months unless there was a “substantial and compelling” reason to increase the term. The judge concluded that Blakely had acted with “deliberate cruelty” and sentenced him to 90 months. Blakely’s lawyers appealed the decision, arguing that because the judge had found their client guilty of “deliberate cruelty,” he had violated the defendant’s right to a jury trial under the Sixth Amendment. The Supreme Court concurred.

“It really rocked the world,” Osler says. “My little world anyway.” Though the case pertained only to state law, the federal sentencing guidelines worked in a similar fashion. “Everyone knew,” Osler says, “the shit was going to hit the fan.”

“Blakely….. WOW!!” Osler’s colleague, Ohio State law professor Douglas Berman, titled his blog post. Berman oversaw a mini media empire for sentencing nerds. He edited the highly respected Federal Sentencing Reporter journal, and six weeks before the Blakely decision came down, he’d started a blog called Sentencing Law and Policy. Both Osler and Berman felt that with the Blakely decision, reformers needed to be, in Berman’s words, “all hands on deck.”

According to Graham Boyd, “Mark and Doug were the most important among the academics working on this.” At first glance, they were an unusual pair. Berman, a secular Jew, had been a law professor the bulk of his career, while Osler had been teaching for only a few years and was trying to bind his Christian faith with his profession. They both believed that the Supreme Court was now open to more reform. Justice Antonin Scalia, considered the most conservative voice on the Court, authored the majority opinion in Blakely, which was supported by liberals like Justices Ruth Bader Ginsburg and John Paul Stevens. The split in the Court over sentencing was not liberal versus conservative but was between pragmatists who wanted incremental change and formalists who wanted to throw out the system of mandatory sentencing.

Six months after Blakely, the Court delivered a landmark decision on sentencing guidelines in United States v. Booker. In a rare instance, the court offered two majority opinions of different aspects of the case. One, written by Stevens and supported by Scalia, addressed the merits of the case and argued the guidelines violated the Sixth Amendment. The other, written by Justice Stephen Breyer, addressed the legal solution and argued the guidelines could be treated as advisory, rather than eliminated altogether. Dissenting from Breyer, Stevens quoted one of Osler’s articles for the Federal Sentencing Reporter.

Breyer’s opinion allowed judges to diverge from the guidelines, but they would continue to be held to a standard of “reasonableness.” “The guidelines still had a significant gravitational force,” Berman says. “Prosecutors were saying, ‘You don’t have to follow them, but it’s a really good idea to keep following them.’” When it came to crack, federal prosecutors went further: They argued that because Congress had specifically sought to preserve the 100-to-1 ratio, it was not reasonable for judges to throw out a congressional mandate.

Osler, Boyd, and Berman began searching for the right case to challenge the sentencing guidelines for crack. Osler filed an amicus brief in a slew of federal courts, arguing that the 100-to-1 ratio was unconstitutional, in the hope that the Supreme Court would eventually take up a case: Perry in the First Circuit, Castillo in the Second, Ricks in the Third, Kimbrough in the Fourth, Spears in the Eighth, and Starks in the Ninth. Each argument was posted on Berman’s blog.

In 2007, three years after Booker, Osler took his students to Washington, D.C., to hear Kimbrough v. United States argued before the Supreme Court. In another victory for the reformers, the Court ruled that judges, applying the sentencing guidelines, could indeed conclude that 100-to-1 wasn’t a reasonable standard.

After the decision was handed down, Boyd and Berman were all over the media—Boyd as the ACLU’s lead advocate for drug-policy reform and Berman as the most prolific sentencing expert. On his own blog, Osler reflected on his role: “There is a part of me that would love to be in the Times and on NPR as a part of this, but then I remember what I teach my own students. I show them … Degas’ ‘At The Milliner.’ There are two women; one is buying a hat while the other is placing it on her head. The woman in the foreground is fully formed and in the light; she will wear the hat and be complimented on its beauty. In the background, the milliner is in the shadows. She made the hat, chose it for this customer, brought it out, but will not be there when it goes out into society to hear the compliments. I tell the students that the lawyer is not the customer, but the milliner.”

As it turned out, Kimbrough wasn’t the victory many thought it was. The Department of Justice continued to resist, arguing that judges couldn’t categorically replace 100-to-1 with a ratio they thought was more just. “Kimbrough was our shot,” says Benham, now a law professor at Texas Tech, and it seemed like prosecutors were “finding a way to wiggle out of it. It was like we won, and it wasn’t complete.”

Many sentencing reformers, including Berman, started to focus on other issues. Osler was no longer filing on behalf of the ACLU. However, he decided to continue working on Spears v. United States. In the case, a judge had sentenced a crack dealer based on a 20-to-1 ratio. The prosecutor appealed, arguing that the Court ruling in Booker barred the judge from establishing his own sentencing ratio and that he should have sentenced based on 100-to-1. The case had already gone up to the Supreme Court once, and the Court had sent it back down in light of the Kimbrough ruling.

When Spears arrived at the Court a second time, it ruled, without oral argument, that judges could now ignore 100-to-1 altogether. Because the decision was delivered the same day as Barack Obama’s first inauguration, Spears did not make the waves Booker and Kimbrough had. Still, congratulations poured in from friends and colleagues. Amid the messages, Osler received a call from Berman. His friend did not begin with the usual compliments. “No celebration, nothing,” Osler recalls. Instead, Berman asked, “What do we do next?”


Osler’s office is on the fourth floor of St. Thomas’s new law school building in downtown Minneapolis. A painting by his father hangs by the door. One of a series, it depicts a man sitting in the back of a church. Above a couch, Osler’s Yale Law School diploma fits awkwardly in a too-large, fake wood frame. “I got that at the Dollar General store in Waco,” he says. “I had it taped to my wall originally.” Displayed on the coffee table is Christ and the Gallows, Or, Reasons for the Abolition of Capital Punishment, a book first published in 1870.

It’s early in the fall semester, and Osler is holding a yellow-brown packing envelope that just arrived. Without opening it, he knows what’s inside: documents pertaining to a trial that concluded with the defendant spending years or, more often, decades in prison. He points to the six stamps, in two neat rows of three. Four have either “liberty” or “justice” written beneath an image of the American flag; two feature the Statue of Liberty. Osler pays attention to the stamps, because he knows they represent a lot of labor. Inmates make only 45 cents an hour.

The envelope is from Roy Blount, a prisoner in the federal penitentiary outside Beaumont, Texas. “Sentenced to life, conspiracy, selling crack,” Osler says. “I know who this guy is.” Blount’s public defender had already reached out to Osler. He reads from the transcript. Blount wasn’t even the one selling; he was a lookout, pointing people to where they could purchase the drugs.

“Well, if he’s a kingpin,” Osler asks, “how much money does he have?” He flips to the sentencing portion of the file. Before determining the punishment, judges look at the convict’s life and possessions. Osler reads from Blount’s testimony: “I hang at a store begging for nickels and quarters and dimes. I stayed at the front porch of my mama’s house. I don’t, I don’t sell dope. I didn’t even have one change of clothes. I had to do my wash every day, judge.”

Osler looks up and asks, “This impoverished ninth-grade graduate is your drug kingpin?” He shakes his head. “I get these every day.” He gestures to a bookcase. Dozens of unopened yellow-brown envelopes are piled on top of one another. Many arrived when he was on summer vacation, and he hasn’t gotten to them yet.

On the surface, Osler’s decision to leave Baylor in 2010 for St. Thomas doesn’t seem like a natural step. Unlike Baylor Law, which has been around for more than 150 years, St. Thomas’s law school is only 15 years old; it ranks 124th, according to U.S. News and World Report, 70 spots below Baylor. Part of the appeal of St. Thomas was that it offered a lighter teaching load and more time to focus on public policy. Osler still has close ties to Baylor, but he was ready to go to a school that offered more flexibility integrating faith with scholarship. “There’s no institution I’ve ever been close to that worries more about orthodoxy than Baylor,” he says. “People there were constantly talking about ‘What does it mean to be a Baptist university?’ And it usually came down to, ‘Well, we make people go to chapel, and we don’t have gay professors, and no one writes in favor of abortion.’ Which is really a bizarre way to define it.”

Two months after starting at St. Thomas, Osler wrote a piece for The Huffington Post titled “Repentance of an Anti-Gay Bigot.” “I was a bigot,” he wrote. “My bigotry was consistent with what the culture, the church and my friends thought and said, and it was not countered by those who knew better.” He credited gay men and women, who had showed him “undeserved grace,” for gradually changing his view. In 2012, he lent his voice to the campaign that prevented an anti-gay-marriage amendment from becoming law in Minnesota.

At Baylor, Osler had been discreet about his work with the ACLU. By contrast, St. Thomas encouraged him to start the first federal commutations clinic in the country. Over the past three years, the clinic has prepared petitions for seven prisoners, which ask President Obama, in Osler’s words, “to grant mercy.” The students in the yearlong class choose among the yellow-brown envelopes that sit on Osler’s bookshelf.

Osler’s interest in clemency heightened after the 2008 election. Along with many others, he thought Obama’s election would signal a shift in sentencing law and the war against drugs. “We think the tide in Washington and elsewhere is beginning to turn in our favor,” wrote the pro-reform group Families Against Mandatory Minimums in a post-election statement. Even the ever-skeptical Berman wrote a post titled “Are We on the Verge of a New Changed Era concerning Federal Sentencing Law and Policy?”

The Spears decision only amped up the excitement. Osler blogged that the decision “should encourage the Obama administration to pro-actively use its power of commutation to lessen the sentences of those who are serving unduly harsh crack sentences.”

Osler hoped the administration would embrace the president’s clemency power. Under the Constitution, the president can forgive a crime (a full pardon) or let a prisoner out early (commutation). Under Bill Clinton and George W. Bush, pardons and commutations had often been awkward and messy. Clinton pardoned Marc Rich, a tax evader who was the husband of a major Democratic donor. Bush commuted the sentence of former vice--presidential adviser I. Lewis “Scooter” Libby, who was convicted for his role in exposing a CIA operative. What was supposed to be a tool for curbing congressional excesses had become a tool for granting political favors.

Initially, from Osler’s perspective, the policy debate under Obama seemed to be moving in the right direction. Transition documents discussed the need for drastic sentencing reform, especially when it came to the crack-cocaine disparity. Although the Supreme Court had weakened the sentencing guidelines, only Congress could undo the mandatory minimums, many of which were tied to the disparity, like the five-year minimum for possession of crack.

In 2010, the Democratic-controlled House and Senate began to consider the Fair Sentencing Act. Osler and other reformers hoped the crack–powder cocaine disparity would finally disappear. The bill did eliminate the five-year minimum for crack possession, but rather than erasing the disparity, it introduced an 18-to-1 ratio. Crack, it seemed, still bore the stigma it had 15 years earlier. The law wasn’t fully retroactive, so many of those who had been sentenced under 100-to-1 still faced decades in prison.

“My first reaction was ‘This is abominable,’” Berman says, “and everyone shouted me down and said be grateful we got something. To call it half a loaf is to insult bread. It’s more like a slice.”

Osler was more measured about the bill’s failings. “That whole negotiation was so fragile,” he says. “Is it what it should have been? No. But it’s what seemed possible.”

Nkechi Taifa, the Open Society Foundations’ senior analyst on civil and criminal--justice reform, immediately began looking for the next step. Taifa had been active in the civil-rights movement of the 1960s and the black-power movement of the 1970s. By the 1990s, she saw sentencing reform as “the civil-rights issue of our time” and became an early advocate, organizing conferences and lobbying Capitol Hill. Osler calls her a legend in the field of sentencing. She suggested to groups that they push for some sort of “blanket pardon” from the president for those still in prison. “That didn’t even get much traction in my progressive circles,” she says. “People said that’s not going to happen.”

In 2011, while she was poking around databases, she happened on an article by Osler called “The Ford Approach and Real Fairness for Crack Convicts.” Published in the Federal Sentencing Reporter, the piece proposed creating a system of commutation panels for crack defendants similar to those President Gerald Ford had established for Vietnam War draft evaders. “Mark was my dream come true,” she says.” She got in touch with him and invited speakers to discuss his proposal on Capitol Hill.

Osler soon entered the world of Washington lobbying. As a reformer, he had a perfect résumé. He uses words familiar to Christian conservatives and sympathizes with the needs of prosecutors. “Mark is a very credible advocate in the sense that he’s not one of the usual suspects,” Boyd says. “He’s not being a soft-on-crime person. When you’re coming from the ACLU, it’s a lot easier to be pigeonholed.”

Osler’s articles and op-eds became more frequent, and he began appearing on outlets like MSNBC and CNN. After his commutations clinic was up and running, he traveled to other universities, including Stanford and Harvard, urging them to start their own. When former Governor Robert Ehrlich of Maryland, a Republican, began a clinic for pardons at Catholic University, he modeled it on Osler’s program. In 2012, Taifa and Osler, along with others, met several times with White House and Department of Justice officials.

Until late last year, the lobbying seemed to have no effect. Obama has granted the fewest pardons and commutations of any president in history. Over Thanksgiving, Osler, Berman, and others wrote about the irony in the president pardoning a turkey while leaving thousands of people in prison sentenced under laws many Republicans as well as Democrats now agree were far too harsh. Berman was particularly cynical, writing that he no longer believed the White House’s claims to be interested in clemency reform.

Then things began to change. Right before Christmas, Obama commuted the sentences of eight people convicted of crack crimes. At a New York State Bar event at the end of January, Deputy Attorney General James Cole announced that the administration was seeking other drug cases to consider for clemency. Cole said the Justice Department would work with the Bureau of Prisons to encourage inmates to seek commutations, with the hope that state bar associations would help in preparing the petitions.

Osler was quick to point out the flaws in the administration’s proposal. In a post for MSNBC, he argued that the White House was “only halfway there,” explaining that the president already has 3,500 petitions sitting on his desk. What was needed, Osler asserted, was a system for processing all the requests. Once again, he called for a version of the Ford plan, in which clemency boards considered 21,000 petitions in one year.

If Obama pursued such a course, the political risk might not be as great as many suppose. Conservative think tanks like the Heritage Foundation have joined liberal organizations like the ACLU, the Open Society Foundations, and Families Against Mandatory Minimums in pressing for reform. Republican Senator Mike Lee of Utah and Democratic Senator Dick Durbin of Illinois have co-sponsored the Smarter Sentencing Act. Introduced last summer, it would reduce mandatory minimum sentences for drug offenders and allow the nearly 9,000 in prison for crack crimes under the old 100-to-1 regime to return to court for a new hearing. In late January, the bill passed out of the Senate Judiciary Committee with support from Tea Party Republicans Ted Cruz of Texas and Jeff Flake of Arizona.


“What the defendant does is threaten the things that our society rests upon: our economy, our family, our ability to defend ourselves, and our cultural heritage. What if we listen to him? What if we did what he said?” On an early afternoon in November, Osler addresses an audience of about 50 students, professors, and priests at Loyola Law School in New Orleans. No one stirs as he makes his closing argument that Jesus Christ should receive the death penalty. “Everything that makes our economy go forward would be gone. That’s what he teaches. That’s what he taught consistently. Is he dangerous? Yes, he’s dangerous!”

Less than a year after he arrived at St. Thomas, Osler set about reviving the trial of Christ he had put together ten years earlier in Waco. This time, however, he wanted to take the show on the road, traveling to churches, seminaries, and schools to highlight the special relationship he believes Christians should have with criminal justice. Rather than spend hours enacting the entire trial, the new format focuses on the sentencing portion. Jesus would be presumed guilty of blasphemy, but it was up to the “jury” to determine whether he should receive the death penalty. Over the past two years, Osler has performed the trial 16 times at institutions like Regent University, the school Pat Robertson founded in Virginia Beach, Virginia, and Fuller Theological in Pasadena, California, considered by many the country’s leading evangelical seminary.

His opposing counsel in the trial is a Chicago public defender named Jeanne Bishop. When Bishop was 30, her sister, who was pregnant, and brother-in-law were murdered in their home. The 16-year-old killer offered no motive and was sentenced to life in prison. A member of the Fourth Presbyterian Church, who sometimes quotes Bible verses to friends having a bad day, Bishop has recently attempted to reconcile with the killer. Tall and thin, with an intimidating gaze, she presents a striking figure in the courtroom, even a mock one. She’s used to defending poor black kids who don’t garner nearly as much sympathy as Jesus.

Osler makes a worthy opponent. He never raises his voice or descends into staginess; instead, he maintains an earnest concern. During the first part of his close, he highlights the stickier parts of the New Testament: when Jesus said he had come “to set a man against his father, a daughter against her own mother,” or when Jesus was being arrested and allowed an apostle to lop off a slave’s ear (which he later healed). “These are the parts no one ever preaches about,” Osler told me beforehand. The Bible he carries is marked up like a law document and has so many tabs he sometimes has trouble finding the passage he’s looking for.

The trial isn’t scripted. Not only do Bishop and Osler not know what the other will say, but they don’t know how witnesses, like the apostle Simon Peter, who are played by people in the community, will respond to their questions. The performers must abide by the Bible, but everyone approaches the roles differently.

During Osler’s lengthy questioning of Simon Peter, whom he treats as a hostile witness, he zeroes in on Jesus’s power. “You’ve seen other things that demonstrate certain powers—a form of magic, really—displayed by the defendant. For instance, his ability to walk on water,” he says to the young man playing Peter.

“I wouldn’t consider it magic, really,” the man replies.

“Have you met anyone else who has that ability?” Osler shoots back.

Bishop’s job is less transgressive, as she makes a plea for the life of Jesus in front of audiences, most of whom believe in his divinity. She points to his good works, his attempts to get away from crowds, and his focus on nonviolence. “No one is beyond the forgiveness of God,” she says.

This is the most explicitly religious project Osler has tackled. He makes a point of performing the trial in front of skeptical audiences. In general, Osler does little to engage with progressive Christians because, as he puts it, “they’re not the people I have to convince.” During a question-and-answer session at Loyola, Osler reiterates that his purpose is to challenge Christians on the death penalty. “The death penalty would not exist in the United States without Christian support,” he says. So far, only one jury has sentenced Jesus to death.

When Osler discusses his faith, he comes across as someone who is comfortable in his own skin, capable of making bad jokes and trenchant observations in the same breath. His earnest questions and his willingness to grapple publicly are rooted in a deep certainty—in God, in faith, and in his place in the world. In his view, everything he does connects to a central belief that he is a Christian and should therefore try to cultivate mercy where it’s lacking and justice where it’s needed.

In the tradition of Anabaptists, Osler is non-creedal and never joins in when his church begins prewritten prayers. His prayers are his own. “A creed is written by someone else,” he says, “and because of that, it’s someone else’s statement of a relationship with God.”

As some of his admirers note, Osler doesn’t conform to the standard expectations of an evangelical. He doesn’t abstain from alcohol, he doesn’t regularly say grace before meals, and he’s not eager to convert nonbelievers. Even the way he talks about abortion is not hard-line. “If a baby is capable of being born alive, I really struggle with justifying the practice,” he says, explaining that he believes the state should offer to assume the costs of delivery and early care for any woman considering abortion at the point the fetus is viable.

But Osler’s identification with evangelism is strong. “An evangelical means you’re unashamed of your faith, you’re willing to let other people see it,” he says. “That’s a form of evangelism. I talk about faith all the time. I don’t always do it in a way that’s conscious. It makes some people uncomfortable.” Osler says he wants to reclaim the word “evangelical,” in the same way that the radical gay-rights group Queer Nation uses a slur as a term of empowerment. “Embracing the word and defining it for yourself is a powerful thing,” he says. “I want ‘evangelical’ to mean someone who is deeply broken and seeks community.”

The idea of being broken and seeking community—whether you’re a drug dealer serving a prison term or a former prosecutor seeking reform—is fundamental to Osler. It was why he ended his sermon at First Covenant Church not with a passionate plea for social justice but with an account of his own vulnerability. He described spending the previous July teaching in Rome. Many days, he felt lonely and grumpy, wandering the city and taking a strange solace in the toys sold in piazzas by immigrant men—little rockets that shot up and then helicoptered down with a glowing blue light, “like angels.”

One morning, he received a phone call from his parents back in Michigan. “My nephew, who’s eight years old, had died. I traveled to Detroit to see my brother and his wife. Those of us who were left. To try to get over the loss of this vibrant child, the loudest of the gaggle of loud cousins who’d been so full of life. Heartbroken, all of us.”

Women in the audience started to sniffle. People began to realize the sermon had taken an unexpected turn, that it was going somewhere far more personal than they anticipated.

After the funeral, Osler returned to Rome and found himself in the piazza where the immigrant vendors sold the rockets. He approached a vendor who spoke little English or Italian and asked if he could buy one. “He looks behind me, and he says, ‘Where is the child?’ And there was something about that question that just broke me.”

The pauses between Osler’s sentences became more frequent, the words more halting.

“I told him in English, ‘There is no child.’ Then something changed in him. Because he may well have been from a country where children who are eight years old die. They die of diseases that are curable. They die because they don’t have enough food. They die because the roads are bad and they get hit by a car. They die from drinking the water.

“There’s something that just softened in him in that moment. He looked at me and said something that I understood to be, ‘What happened?’ And I told him, ‘My brother was canoeing with his son, and the boat capsized, and rescue didn’t come soon enough. My brother survived, and his son did not.’

“And I cried. He didn’t say anything. He reached out and touched me on the shoulder and he gave me this.” Osler pulled out a toy that in any other context would look like schlock but at the moment had all the weight of a holy object. “The man put his hands out that he wouldn’t take payment—because he was from a place where children die.

“That was grace. And it’s grace that seeps into the cracks of ourselves, if we let them be seen, let ourselves be vulnerable, let ourselves get to that place where we can both show mercy and receive it. Because it is the same place. Grace can come, our unclean spirits cleansed, if we acknowledge in our hearts the essence of humility that there is a god and that is not me. The god that is—the god that is—turns the world upside down.

“Lord, you are greater than our imagination. Let that humility be a force in our lives. In our chasteness, drive us to what is good. Amen.”

Osler smiled and sat down.

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