Since 1988, the gold standard for Daily Double betting has been Bob Beers. Making his debut on April 7, 1988, Bob did something that had never been done before, and has never been done since. He bet $10,000 ($20,000 in today’s terms) on a Daily Double. This was his second massive bet of the round, having bet $6,000 ($12,000 today) six clues earlier. He got them both, leading to a score before Final Jeopardy of $27,000 ($54,000 today). While he missed Final Jeopardy and only won $23,000 – he became the first of only two players to get a pair of $10,000+ Daily Doubles correct in the same game.
October 26, 1989. Steve Berman’s third game. Steve had a massive $6,700 ($13,400 today) after the Jeopardy! round, and took it to challengers Paula Long and Larry Linsey in the Double Jeopardy round. Holding a $10,100-$1,700-$900 lead when finding the first Daily Double, he picked up $5,000 ($10,000 today) on what turned out to be his second-largest bet of the day. The steamroller kept moving, and while Larry made an attempt to catch up, Steve found the last Daily Double late in the game with a $15,900-$2,300-$2,100 lead. He went for the jugular with a $7,500 ($15,000 today) bet. Inexplicably, Alex Trebek and the judges elected to prompt for “be more specific” on Bach on the following clue:
German composer who produced over 1,000 works & 20 children, including 5 named Johann & 1 named Johanna
Steve gave Edward when prompted and his score fell to just $8,400. This is still the record for the most amount of money lost on a single Daily Double. He dropped another $4,000 in Final and only won $4,400 that day.