The thing that makes James' strategy work is that by going to the bottom and getting the correct answers for the $1k and $2k clues means he has more to bet when the DD are chosen. So if he got all 6 $200 clues correctly before he hit the DD, then he has only $1,200 to bet. If he gets all 6 $1k before he hits the DD, he has $6k to bet, and (assuming the answer is correct) he would have $12k instead of $2,400 going into round 2, even if he answers no other questions in round 1. And so it goes.
I still groan and roll my eyes when he gets the third DD, because by that time, the game is all but over.
I'll preface by stating that I'm not a sports fan and watch very little. I usually don't watch the Super Bowl, and sometimes don't look at anything other than a few of the ads after the fact. However, I would be more likely to tune in to even a few minutes of the SB if the outcome didn't seem to be a foregone conclusion.
I still like Jeopardy!, but I like to watch it more when it's a contest and not a steamroller. Runaways aren't nearly as fun to watch as a close game is. In my humble opinion.