"He was outraged by injustice," said Arthur Spitzer, legal director of the ACLU of the National Capital Area.

Carliner died of a heart attack at George Washington University Hospital. He was 89.

Carliner's advocacy was in pursuit of often unpopular causes. He challenged laws, both federal and state, on segregation, illegal immigration, miscegenation and homosexuality. He was also instrumental in gaining for Washington, D.C., a mayor and city council, although he regretted the limited nature of the representation he helped secure for the city's residents.

A native Washingtonian whose father owned and operated grocery stores, Carliner was never retiring when he percieved that injustice was being done, according to those who knew him. In addition to his run-in with authorities outside the German Embassy, he earned the disfavor of his high school principal by calling for student demonstrations over the cancellation of a football game. The principal would write a letter to George Washington University that resulted in Carliner being denied admission later that year.

He went on to attend American University and the University of Virginia and its law school, from which he was expelled for his political activity and distributing political material. In 1941, he finished his law degree at National University, which was later to merge with GWU to become the National Law Center of George Washington University.

Carliner enlisted in the Army that year and attended Officer Candidate School, but claimed he was denied a commission because of his political views.

After the war, Carliner would begin to practice law and make a name for himself handling high-profile, controversial cases.

In the 1954 Naim v. Naim, Carliner argued that Virginia's miscegenation law violated the Constitution. In the late 1950s, he sued to overturn Virginia's prohibition on integrated seating at public events. In 1965, he won a landmark decision, on appeal, for a federal employee who was fired for soliciting gay sex. And in 1966, he won a case that would expand the rights of U.S. citizens to travel abroad.

One of Carliner's major contributions to law was in the area of immigration. In a series of cases that ranged from fighting the deportation of a Nicaraguan illegal immigrant to overturning a presidential order for federal agents to compile dossiers on 50,000 Iranian students, he sought to liberalize the country's immigration policy. In the process, he helped define modern immigration law.

"He made it a field of legal practice," said Spitzer of the ACLU-NCA. "He helped shape the ACLU's view on immigration."

Carliner was a founder of the Washington, D.C., ACLU affiliate and became its first president in 1962. He was active locally and nationally in the organization for more than 40 years.

Ralph Temple became legal director of the ACLU-NCA in 1964, when Carliner was chair. He remembers him as "a highly principled guy, passionate about civil liberties."

And he stood up for himself. In 1977, Carliner sued when a homeowner in Northwest Washington sold his house to another family rather than to Carliner, saying to Carliner's real estate agent, according to a Washington Post article, "I'll let the house stand there and rot before I sell it to those Jews." Carliner got the house.

He had "a strong secular Jewish identity," said his daughter, Deborah, of Washington, D.C. He served as president of the Washington chapter of the American Jewish Committee in 1970-1971.

In 1999, he became a patron of Theater J at the Washington DC Jewish Community Center.

"He was a benevolent and kind supporter of our theater," said Ari Roth, artistic director of Theater J. "Always a warm and encouraging presence, he brought his family onboard and they became a very important force at Theater J."

One of what Roth called their "Producing Angels," Carliner had been one of the theater's original large donors, and continued to contribute annually as well as support one production each year ‹ plays that "reflected his liberal consciousness," said Roth.

He was also a patron of InSeries, which produces a variety of musical performances.

Carliner wrote The Rights of Aliens in 1977, a guide to changes in immigration law. In 1990, he co-authored The Rights of Aliens and Refugees.

He was the founding chair of the International Human Rights Law Group, now called Global Rights.

Carliner's wife of 50 years, Miriam, died in 1994. In addition to his daughter, he is survived by his son, Geoffrey of Newton, Mass.; four grandchildren; and one great-granddaughter.