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I, too, have danced with the cruel mistress that is Jeopardy. I consider myself lucky that, unlike Messrs. Jennings and Bayard, none of my (four) misses on Final Jeopardies cost me the game -- either I was untouchable or too far behind. That doesn't mean they still don't hurt (I'm looking at you, Duke of Windsor!)
One thing to add to Bayard's analysis is that once you're on (and eventually off) Jeopardy that that's not just the end of Jeopardy, but of the practicality of having that well of trivia. Sure, you can gather for events like the ones in Steven's Point and Glendale. A retired NFL quarterback can also play in a weekend game, but it's not the same. I've said quite seriously in the past (and some of the better players I've talked to feel the same) that if I were offered a minimum-wage job for playing Jeopardy 40 hours a week I would take it in a heartbeat.
My only stipulation in the contract would be that I would get to take my 15-minute break during the sports questions.
