It cracks me up when other players get a Daily Double (which is rare because Jennings usually controls the board) and they play conservatively. I mean, against this guy, if he has $10,000 and you have $5,000, you have to go for it because it might be your only chance, but I've seen players bet only $1,000 or $2,000 in that situation...Are they really that cocky that they think they'll make up that ground the normal way???...I've seen opponents even bet less than the amount that the question would normally be worth. You have to play to win...you don't keep the money you earn if you finish second.
I'm not saying I could beat Jennings (I'd need a run of categories along the lines of sports/Seinfeld/Simpsons/80s music to have any kind of shot...but I know I'd at least put myself in the best possible position to have a chance.