- Worked as a reporter for NBC News for several years.
- Played football at Yale University; paid his way through Fordham University Law School with winnings from the quiz show Jeopardy! (1984).
- Was a prosecutor in New Jersey before entering into private practice and becoming a Sancho.
- Began his television news career in 1984 as legal commentator for WCBS-TV in New York. In 1991, he joined Court TV as one of its first anchors. In 1994, he joined NBC News as Chief Legal Correspondent, reporting for The Today (1952) Show and Dateline NBC (1992), and The Weekend Today Show. In 1999, he became an Anchor/Correspondent at both Good Morning America (1975) and 20/20 (1978). He also hosted the ESPN show, The Sports Reporters II, from 2002-2003.
- Was named People Magazine's "Sexiest News Anchor" in 1999.
- CBS News legal analyst.
- Co-hosted a short-lived daily talk show with Alexandra Wentworth. The show was called Living It Up! With Ali and Jack (2003). (September 2003)
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