Alan Berg was born in Chicago in 1934, the son of a Jewish dentist and a clothing shop manager. As a youngster, he had bright red hair and a temper to match. His hobbies were golf, stamp collecting, and photography. At age seventeen he went off to college at the University of Colorado–Boulder, where he was happy to be away from his father, whom he viewed as a hypocritical anti-Semite. After two years in Boulder, Berg transferred to the University of Denver, then the University of Miami in Florida, DePaul University in Chicago, Northwestern University, and then back to DePaul, finally graduating from its law school. In 1958 he married Judy Halpern of Denver, and the couple settled in Chicago, where he practiced law. Berg was an able and successful criminal defense lawyer, and his affable glibness in front of juries served him well.
Berg began experiencing epileptic-like grand mal seizures, surviving all of them but often experiencing depression. He discovered that martinis calmed him down and soothed the anxieties he could not otherwise get rid of. He eventually abandoned his law practice and he and Judy moved back to Denver, where he entered St. Joseph Hospital to dry out. Berg opened his own clothing shop, the Shirt Broker, in Seventeenth Street’s Albany Hotel.

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