The thick envelope that Ketanji Brown Jackson received in the mail in 2005, when she was a federal public defender in D.C., was like many others inmates had sent to her office: laden with stamps and stuffed with court filings and a plea for help.
Jackson, 51, is now a judge on the influential U.S. Court of Appeals for the D.C. Circuit and a leading contender for President Biden to nominate to replace Justice Stephen G. Breyer, who last week announced his plan to retire from the Supreme Court. She would be the first Black woman on the court if she were nominated and confirmed, and the first justice in decades with deep experience as a criminal defense attorney.
Jackson’s brush with her uncle and his prison sentence, which arose out of the nation’s war on drugs, adds to a set of life experiences that would distinguish her from previous justices. Brown was sentenced to life under a “three strikes” law. After a referral from Jackson, a powerhouse law firm took his case pro bono, and President Barack Obama years later commuted his sentence.
Civil rights groups and other liberal advocacy organizations have promoted Jackson for Biden’s shortlist of Supreme Court contenders not only because of her gender and race — Biden has pledged to nominate a Black woman — but because of her varied personal and professional experience, particularly as a federal public defender. Nominees to the federal bench more often have worked as prosecutors and corporate lawyers.
As a public defender, Jackson represented people accused of an array of crimes who could not afford an attorney. Later, as an Obama appointee on the U.S. Sentencing Commission, she helped rewrite guidelines to reduce recommended penalties for drug-related offenses. And as a trial judge for eight years, she sentenced more than 100 people to prison.
Jackson grew up in a high-achieving household in Miami. She was a high school debate champion and went on to attend Harvard University and then Harvard Law School.
She has not spoken publicly about her uncle’s case. Though news accounts have referenced her having an uncle whose life sentence was commuted, his identity, the details of his crimes and his direct appeal to Jackson — along with her response — have not been previously reported.
Jackson’s chambers declined to comment for this article.
The following account is based on state and federal court records, clemency information and interviews with people familiar with Jackson’s experiences at different points in her life. Some agreed to speak only on the condition of anonymity to discuss private matters.
“For Ketanji, the law isn’t just an abstract set of concepts. Her family’s experience does inform her awareness of the real impact the law has on people’s lives,” said a friend and former colleague from the federal defender’s office.
By the time her uncle contacted her, that person said, she was an experienced attorney and “already knew what has become a national consensus that the nation’s drug laws were overly harsh.”
Jackson saw Brown, her father’s older brother, infrequently while growing up in the Miami area in the 1970s and 1980s, according to a person familiar with their interactions. The daughter of two teachers, Jackson spent more time with her mother’s side of the family. Her mother’s brother, Calvin Ross, rose through the ranks to become chief of the Miami police department. Her father studied law when Jackson was a young child and went on to become the local school board’s attorney.
In 1976, when Jackson was 5, her uncle’s troubles began to surface in court records. Brown, then 37, was arrested and charged with carrying a concealed firearm as well as possession of heroin and possession of drug paraphernalia.
While that case was pending, Brown was standing outside a Miami laundromat as police approached. A man nearby handed something to Brown, who threw it to the ground, his defense attorney said, according to a transcript of court proceedings. Brown was arrested for alleged possession of heroin.
The latter charge was not pursued by prosecutors, but Brown pleaded guilty to the earlier gun and drug possession charges — both felonies — and was sentenced in state court to 18 months of probation.
Six years later, in 1982, Brown was back in court in the Miami area. This time, the charge was possession of at least 20 grams of cannabis, a felony at the time. Brown pleaded guilty in state court and was ordered to pay a fine of $1,500.
In 1989, when Jackson was a freshman at Harvard, Brown was 50 and mixed up in South Florida’s notorious cocaine trade. On April 18, Brown pulled his El Camino up to a Miami home, unaware that five federal agents were staking out the house. Brown left a few minutes later with a black nylon gym bag, placing it on the passenger seat. The agents followed. They soon stopped Brown and found the gym bag filled with what federal authorities later said was 14 kilograms of cocaine, wrapped in duct tape, court records show.
Brown was indicted on charges of possession of cocaine with intent to sell and conspiracy to commit that offense. Several months later, a jury in federal court found him guilty of the first of those crimes. A federal law that had recently taken effect ratcheted up punishments for repeat drug offenders, mandating life in prison in certain cases after a third drug offense.
U.S. District Judge Lenore C. Nesbitt rejected the argument from Brown’s attorney that his client should be sentenced under the old rules, which would have added 20 years for his two past drug offenses, according to a court transcript. The judge said she had no choice but to impose a life sentence because of those prior convictions. Brown’s punishment was upheld on appeal.
Jackson had not seen or heard from her uncle in more than a decade when Brown first called her at the federal defender’s office in 2005, the person familiar with their interactions said. By then, Jackson had worked as a clerk for three judges, including Breyer at the Supreme Court. She had been in private practice in Boston and D.C. and spent two years as an assistant special counsel on the sentencing commission.
“Can you help me? I’m in jail,” Brown told Jackson in their first phone call, according to the person with knowledge of their interactions. “Your dad tells me you’re a public defender.”
Jackson’s former colleague and friend recalled talking with her about the stamp-laden envelope she received later from her uncle. Jackson felt sympathy for his situation, the former colleague said.
Jackson’s office, however, represented only people convicted in federal court in D.C. Her uncle had exhausted his appeals in court, and she had no immediate options to recommend, the person familiar with their interactions said. In 2008, she referred him to a powerhouse private law firm, Wilmer Hale, after learning that attorneys there handled clemency cases free of charge.
In a statement to The Washington Post, Wilmer Hale said Jackson referred the case “years before she became a federal judge. She had no further involvement in the matter.”
Brown’s push for clemency eventually overlapped with a national bipartisan effort to undo harsh mandatory sentences that had been imposed on nonviolent drug offenders.
The Obama administration’s Justice Department played a key role in that effort by aggressively reviewing clemency petitions. In eight years, Obama commuted the sentences of more people than the past 12 presidents combined, with a focus on nonviolent drug offenders. More than 1,700 people had their sentences commuted.
Larry Kupers, the deputy pardon attorney at the Justice Department when Brown’s sentence was commuted, said it was not unusual during Obama’s presidency for high-profile law firms to represent inmates seeking clemency.
At Obama’s urging, Congress passed the Fair Sentencing Act in 2010, lowering some mandatory minimums for drug offenses. The law did not apply retroactively, but the Justice Department began encouraging federal inmates to petition to have their sentences commuted to fall more in line with what they would have been under the revised law.
By 2014, the clemency initiative expanded to include efforts to address “the worst of” three-strike convictions, Kupers said.
Kupers said someone with Brown’s criminal background would have fallen squarely into the category of those the Justice Department saw as eligible for relief.
That same year, Wilmer Hale filed its petition on behalf of Brown, the firm said.
As the Justice Department was focusing on clemency for those already in prison, the U.S. Sentencing Commission — with Jackson as a member — was taking steps to adjust sentencing guidelines. That effort, too, had bipartisan support.
In 2014, as a vice chair of the commission, Jackson backed a proposal to make sentencing guidelines for most federal drug trafficking offenders less severe. Months later, the commission voted to apply the reductions retroactively, a move that expedited the release of tens of thousands from federal prisons.
“It was probably the biggest decision the commission had ever made,” said Rachel E. Barkow, who served with Jackson on the commission at the time.
The commission’s actions were informed by five years of data that showed shorter sentences for crack-cocaine convictions resulted in lower recidivism, she said. The changes did not affect sentence “enhancements” under three-strikes laws, such as those Brown had received.
On. Nov. 22, 2016, two months before he left office, Obama commuted Brown’s life sentence along with those of 78 other drug offenders. Jackson learned about her uncle’s planned release when she looked up the public list of names, according to the person familiar with her interactions with Brown.
Jackson did not submit a letter or communicate with the Obama administration on her uncle’s behalf, the person said.
W. Neil Eggleston, Obama’s White House counsel at the time, told The Post he had no recollection of Jackson contacting the White House.
Brown was 78 years old and in fragile health when he was released the next year. Jackson’s parents saw him on one occasion in Florida, the person familiar with her interactions with Brown said.
Brown told them that he was moving to Georgia with a friend, the person said, and Jackson’s parents had not heard from him since. He died in 2018, less than a year after his release, according to public records.
Alice Crites contributed to this report.