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Veteran jurist to hear Obama case

Leonard Shapiro among longest-serving immigration judges in US

Onyango Obama in January 2013, leaving the JFK federal building after his arraignment on immigration charges. John Tlumacki/Globe Staff

Boston immigration Judge Leonard I. Shapiro had just ordered the deportation of Ariana Lima’s troubled young son to Cape Verde when Lima jumped up and rushed toward the judge’s bench. Two sheriff’s deputies chased her. But the white-haired judge raised a hand and signaled for them to stop.

In tears, Lima sank into a chair and begged Shapiro to reconsider. Her son, then 22, had a long criminal record, but she said his father had been abusive. She had worked too many hours and left him alone.

“It’s my fault,” Lima said at the hearing last year.

“Ma’am, can I tell you something?” the judge said in a soft voice as he peered over the bench. “It’s not your fault.”


The deportation case is one of thousands that have crossed Shapiro’s desk, but it offers a glimpse of the compassion and conviction that drives the longtime judge as he prepares to consider a much higher-profile case Tuesday, the deportation of President Barack Obama’s uncle, Onyango Obama, to Kenya.

Shapiro is one of the longest-serving immigration judges in the United States, and the only judge known to decide the fate of two relatives of a sitting president, whose framed portrait hangs on the courthouse wall in the John F. Kennedy Federal Building downtown.

At 77 years old, Shapiro is well past retirement age in a court system with conditions that other judges have fled. Immigration courts are notorious for huge caseloads, skeleton staffs, and high burnout rates, and the more than 250 judges have little time to decide emotional cases. And because they are only administrative judges for the Justice Department and not full-fledged federal judges, their powers are often weak and their decisions unenforced.

“The job is a very difficult one, being an immigration judge,” said Harvey Kaplan, a veteran Boston immigration lawyer. “Ultimately, he tries to do the right thing. He’s a mensch, you know? He’s a good guy.”


Colleagues describe Shapiro as a gracious and witty man, a grandfatherly figure who is guided by a strict moral code and a scholar’s devotion to the law. He graduated from the University of Massachusetts, served in the US Army, and then earned a law degree from Boston University in 1961.

He went to work in private practice, fighting to get immigrants out of jail or to help them stay in the United States. He headed the American Immigration Lawyers Association in New England in the late 1980s.

In December 1990, during a Republican administration, the attorney general appointed him to the Boston immigration court.

Many lawyers were pleased to see a former immigration lawyer ascend to the bench in a profession traditionally dominated by federal government lawyers.

“He understands we’re a nation of immigrants,” said William P. Joyce, an immigration lawyer and former Boston immigration judge. “He understands what immigrants bring to the table. And yet he is going to enforce the law.”

Shapiro’s admirers say he has been a fair judge, occasionally short with lawyers who are late or unprepared. He has advocated for pro bono legal services for immigrants, who are not entitled to court-
appointed lawyers.

“I think he believes fundamentally in fairness,” said Sarah Ignatius, executive director of the Political Asylum/
Immigration Representation Project, a Boston nonprofit that aids asylum seekers and immigrant detainees.

In 2011, for instance, Shapiro granted legal residency to a man from El Salvador who had a serious mark against him: a drunken driving conviction more than a decade earlier. But the man had also paid taxes and had been a good father to his children, who live in the United States.


But Shapiro has also been a tough judge, even tougher than many of his colleagues in Boston and nationwide. From 2007 to 2012, he rejected 59 percent of asylum claims, a rate higher than the national average, according to the Transactional Records Access Clearinghouse, a data research organization at Syracuse University.

In 1991, Shapiro made headlines for denying asylum to Patrick Henry Stagg, an Irish national illegally in the United States who had the support of the mayor of Boston and an editorial in The Boston Globe. Stagg, of Dorchester, argued that the FBI had endangered his life by trying to recruit him as an informant against Irish paramilitary groups.

But Shapiro refused to grant him asylum because Stagg had been convicted in Ireland of being involved in one the groups, the Irish Republican Army.

Shapiro also drew criticism for granting asylum to President Obama’s aunt, Zeituni Onyango, in 2010, years after she defied his orders to leave the country and instead settled into Boston public housing.

In his decision, Shapiro said he granted Onyango asylum because a federal official had illegally disclosed her confidential case to the news media, just days before her nephew’s historic election in 2008.

Shapiro’s decision on the president’s uncle, Onyango Obama, is likely to come under just as much scrutiny.


Onyango “Omar” Obama, now 69 years old, came to Massachusetts 50 years ago as a teenager to attend an elite boys’ school in Cambridge, with the help of the president’s late father, Barack Obama Sr. Onyango Obama dazzled classmates with his bubbly demeanor and soccer skills, but he later dropped out of school and disappeared. He was ordered deported to Kenya several times, most recently in 1992, but never left.

He lived quietly in Massachusetts until August 2011, when Framingham police arrested him on drunken driving charges. Obama later admitted in court that prosecutors had enough evidence to convict him, and after a year’s probation and other penalties, the charge was dismissed.

Onyango Obama, who works as a liquor store manager, has declined to be interviewed, and his lawyers did not respond to several requests for comment.

Some critics have said he appeared to receive special treatment, since immigration officials released him from jail despite his outstanding deportation order and gave him a work permit.

After his drunken driving arrest, he famously said, “I think I will call the White House.” However, President Obama was not close to his father’s side of the family.

Some wonder why Shapiro stays on the bench to handle these and other high-stress cases.

The Boston court has a significant backlog of cases. And Shapiro’s eyes and ears are not as sharp as they used to be. On the bench, he is often seen reaching for a magnifying glass to decipher documents.


But others say Shapiro is well prepared to handle the case, which happens to involve a section of immigration law that is rarely used nowadays.

At Obama’s initial hearing in January, his lawyer, Scott Bratton, said he would seek a green card for Obama based on registry, a section of immigration law that allows immigrants to seek a green card if they arrived before 1972.

Obama also must prove that he has good moral character, and whether he does, in the end, will be up to the judge.

Maria Sacchetti can be reached at