The son of a physician, Kunstler was born in New York City and attended DeWitt Clinton High School. He was educated at Yale College, graduating Phi Beta Kappa in 1941, and Columbia University Law School from which he graduated in 1948. While in school, Kunstler was an avid poet and represented Yale in the Glascock Prize competition at Mount Holyoke College. Kunstler served in the U.S. Army during World War II in the Pacific theater, attaining the rank of Major, and received the Bronze Star.

Kunstler gained national renown for defending the Chicago Seven (originally Chicago Eight), in a five-month trial in 1969-1970, against charges of conspiring to incite riots in Chicago during the 1968 Democratic National Convention. Under cross-examination, Kunstler got a key police witness to contradict his previous testimony and admit that he had not witnessed Jerry Rubin, but had rather been given his name two weeks later by the FBI. Another prosecution witness, photographer Louis Salzberg, admitted under Kunstler's cross-examination that he was still on the payroll of the FBI.  The trial was marked by frequent clashes between Kunstler and U.S. Attorney Thomas Foran, with Kunstler taking the opportunity to accuse the government of failing to "realize the extent of antiwar sentiment". Kunstler also sparred with Judge Julius Hoffman, on one occasion remarking (with respect to the number of federal marshals): "this courtroom has the appearance of an armed camp. I would note that the Supreme Court has ruled that the appearance of an armed camp is a reversible error". During one heated exchange, Kunstler informed Hoffman that his entry in Who's Who was three times longer than the judge's, to which the judge replied "I hope you get a better obituary". Kunstler and co-defense attorney Leonard Weinglass were cited for contempt (the convictions were later overturned unanimously by the Seventh Circuit). If Hoffman's contempt conviction had been allowed to stand, Kunstler would have been imprisoned for an unprecedented four years.  The progress of the trial--which had many aspects of guerrilla theater--was covered on the nightly news and made Kunstler the best-known lawyer in the country, and something of a folk hero. After much deadlock, the jury acquitted all seven on the conspiracy charge, but convicted five of violating the anti-riot provisions of the Civil Rights Act of 1968. The Seventh Circuit overturned all the convictions on November 21, 1972 due to Hoffman's refusal to let defense lawyers question the prospective jurors on racial and cultural biases; the Justice Department did not retry the case.

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