In 1993 and 1996, Anastopoulo successfully defended college football coach Charlie Taaffe for two separate DUI charges.

After which, Anastopoulo filed and recovered for Taaffe's wrongful termination from his employer, The Citadel military college.

No reason was given by Anastopoulo for the withdrawal, but it did coincide with a decision by the South Carolina Supreme Court to ban the use of catchy nicknames by attorneys.

[7] In July 2008, a Charleston County jury awarded Anastopoulo's client what was believed to be a record-setting damages verdict of $50 million at the time to a woman whose husband was killed 5 years before in an accident involving a driver that police alleged should have never been behind the wheel.

Defendants included Columbia and the University of Pennsylvania, in an attempt to secure refunds for students whose semesters were cut short due to the pandemic.

[10] In 2022, Anastopoulo filed a class action lawsuit against Procter & Gamble, alleging the company used benzene, a chemical linked to cancer, in its antiperspirants.

The New York Post reported the 6,700 square-foot mansion, built in 2021 and overlooking the Ashley River, is the most expensive residential property in the historic Charleston area.

[14] He worked alongside Sugar Ray Phillips (former middleweight boxing champion of the world) as bailiff and Kato Kaelin.

[13] On April 26, 2006, Anastopoulo, his wife, and two daughters attended the 33rd Daytime Emmy Awards at the Kodak Theatre in Hollywood, California.