Few people know that I'm a one-time Jeopardy champion. It’s not something I like to talk about, and with good reason. But my friend, Jack, has advised that, for my own peace of mind, I should go public—make a clean breast of what happened—and I respect his judgment, so am taking his advice.

The show was taped some years ago. I was thrilled just to be on it and, quite frankly, didn’t expect to win, for my opponents were daunting, to say the least. Bill was an Oxford-educated high school history teacher from New York who'd just been voted best teacher on the Eastern Seaboard. And Claire, the returning champion, was an antiquities scholar and part-time librarian from Wisconsin whose disarmingly soft voice and string of nine decisive wins, when the shows aired, would set the Jeopardy world abuzz with adoration and talk of history in the making. Against these two I’d need a miracle.

Whatever my chances, I was determined to give it my best shot, and did. But so did Bill and Claire and, for the entire first round, the action switched back and forth between the two of them and I might as well have been in the audience. I was a donkey in a horserace. I was little more than part of the set.

But then, as the Double Jeopardy categories were revealed, my prospects brightened. We were to be tested on our knowledge of Canada, 50's music, space travel, palindromes, ancient cities, and the American Revolution. Perhaps I’d a chance, after all.

The ancient cities category was Claire’s for the taking and she took it with ease. And Bill sure knew his space travel. But I had an unexpected edge in the American Revolution category, for I’d noticed it was a popular category and had studied it enough that, to my American opponents’ surprise, and Alex’s, I quite handily ran the category. And the remaining categories? Having been a Canadian teenager in the 50‘s and loving anything to do with words, I couldn’t have been happier and, by round’s end, Claire was leading with $14,500, Bill had $11,600, and I had an even $10,000. As Alex said, it was anybody's game.

The Final Jeopardy category was “20th Century Magazines”. Whatever the category, I’d planned to wager it all, so did. Then came the clue—“The Saturday Evening Post’s first 500 covers included this many photographs." I’m not sure, now, it was 500, but that was the gist of it.

The countdown started and, from the corner of my eye, I could see that Claire was already writing her answer. She hadn’t even had to think about it—knew it right off, like it was common knowledge. It sure wasn’t to me. Now Bill was writing something, too. Starting to panic, I took a deep breath and refocused—the Saturday Evening Post—I’d loved its cover illustrations as a kid, especially its Norman Rockwell covers—had there ever been photo covers?—I couldn’t remember seeing any and, time running out, hurriedly scrawled ‘WHAT IS’ and had just started 'NONE' when the buzzer sounded and we had to put down our markers.

My score being the lowest, Alex came to me first. "Tom, you were struggling, I noticed—were you able to come up with the right answer?"

My answer was revealed.

“You were, indeed! Good for you! That first-time use of a photograph proved so unpopular with readers, the Post immediately returned to illustrations and stayed with them, exclusively, for many more years. And how much did you wager? Everything! Putting you in the lead with $20,000.” 

He then moved to Bill. Like me, Bill had guessed ‘none’ but, unlike me, had had the presence of mind to write ‘WHAT IS 0?’ and lost all but $200. Then to Claire. Did she have the right answer? She did. And how much had she wagered? She was smiling but shaking her head. She'd only wagered $5,000. I had beaten her by $500 and here, now, was Alex pumping my hand and telling me I’d done Canada proud. For failing in my attempt to stupidly spell out the wrong answer, I was the new Jeopardy champion and $20,000 richer.

“It bothers me, still, that I didn’t speak up,” I said to Jack, “that I didn’t come clean to Alex about my ‘1’ and cede the win to Clair. Had I done so, she might well have gone on to be another Ken Jennings and, by now, be rich and famous and have a book on the New York Times best-seller list.”

Jack said that dwelling on what might have been is pointless and stupid and would make me crazy, maybe already had.

“I let myself down,” I said. “That’s what bothers me most. I didn’t do the right thing.”

“Oh, come on—give yourself a break. As I recall it, that $20,000 got you out of a pretty deep hole at the time. You were a starving man found himself at a banquet. No one in your shoes would have done any different.”

“I imagined myself a man of integrity.”

“You imagined it on a full stomach,” he said.

He suggested I write about it—maybe that’d help.