Although any recording of it seems to be lost to history, Art Fleming recounts in The Jeopardy! Book that he was the chosen Secret Square for one particular game on the original series. Asked a question about tennis players, he genuinely had no idea (the celebrities were briefed in advance on some questions, but apparently not for the Secret Square ones) and guessed one of the three choices at random. Asked to agree or not, the contestant said "Art Fleming would never lie. I agree!" Thankfully, Fleming's guess was correct and won the contestant over $11,000 in prizes. note Such an episode likely aired in the late 1960s, at a time when Secret Square jackpots started in the $1,000-$1,500 range.
Anytime a contestant wins a Secret Square that has, through going unwon for several episodes in a row, has accumulated to a large amount. In the late 1970s, Secret Square jackpots often reached $25,000 and at least one topped $40,000, while at least one Bergeron-era episode grew to $50,000 before being collected.
For die-hard game show fans, the two Game Show weeks in 2002 and 2003, where veteran game show personalities such as Bob Eubanks, Charles Nelson Reilly and Brett Somers, and Wink Martindale were on the panel. Former Let's Make a Deal model Carol Merrill, Wheel of Fortune letter-turner Susan Stafford and High Rollers model/dice roller Ruta Lee modeled the prizes, and Rod Roddy announced on the first week (with Shadoe returning for the second week). And, of course, Peter Marshall was the center square, and traded places with host Tom Bergeron on the first week's second-to-last episode.
Peter: Object for the players is to get three stars in a row, either across, up-and-down or diagonally; it is up to them to figure out if a star is giving a correct answer or making one up; that's how they get the squares. A game is worth a tho — A THOUSAND DOLLARS?![stunned] Whoa! Times have changed...!
Certain contestants fall under this category as well:
Tarek Tolba, who not only won three cars during his five-show run (for a total of $154,521), but never lost a game.
Jenny Thomas, who became the biggest winner in the history of the franchise. She won a "Close but No Cigar" week (highest scores amongst non–five-day champs competed for a slot in that year's Tournament of Champions), and went on to win the Tournament and $50,000, ending up with a grand total of $196,175.