Michael Shutterly FromRichmond, Virginia AppearanceFile:Flag USA.png August 24 & 25, 1999 (original run)May 24, 2000 (Champions Edition run) Money won Michael Shutterly, a lawyer, coin collector and leader Boy Scout from Richmond, Virginia, was a contestant on season 1 of the U.S. version of the show on August 24th-25th, 1999. He walked away with $500,000. He held the record for the largest single win in United States game show history, until it was broken by John Carpenter who won $1 million almost 3 months later.