2005 Ultimate Tournament of Champions Round 1 player: $5,000.
1990 Tournament of Champions winner: $100,000.
1990 Super Jeopardy! semifinalist: $10,000.
Season 6 5-time champion: $82,501.
In his second game (#1149, aired 1989-09-07), Bob tied the single-day cash winnings record of $27,800, set by Kevin Frear in his second game (#902, aired 1988-07-05). Kevin had broken Harvey Becker's record of $25,400, set in Season 2 (#304, aired 1985-11-07). Kevin's record lasted for over 4 years, when it was broken by Frank Spangenberg's $30,600 finish in his fifth game (#1241, aired 1990-01-15).
In his fifth game (#1152, aired 1989-09-12), Bob's five-day winnings record of $82,501 broke Chuck Forrest's then-record of $72,800 for most cash winnings in regular games, which Chuck had set nearly four years before on show #280, aired 1985-10-04. Because Bob's winnings were higher than the then-limit of $75,000, $7,501 of his winnings were donated to his selected charity, Oxfam. Bob was the first player to have to make such a donation. Bob's record stood for only a few months until Frank Spangenberg earned a five-day total of $102,597 on show #1241, aired 1990-01-15. Frank, too, had to donate a substantial portion of his winnings to charity--$27,597 to the Missionaries of Charity in New York City.
Bob appeared on To Tell the Truth shortly after winning the Tournament of Champions as a mystery personality in its "One-on-One" segment.
Jeopardy! Message Board user name: Canuckistan