Brad got REALLY lucky that Jennings missed the final question - Brad got the question RIGHT, but bet NOTHING. Ken woulda torched him since he bet a lot of cash. That is, if Ken had gotten it right !!!
The other guy - you had to feel for him. Foolishly bet the farm on the Daily Double the first day and tanked. On the second day, he HAD to bet the farm on the Daily Double again to get back into it - and missed AGAIN !!!
Unfortunately, these were not the three greatest players. Brad and Ken were, but they mentioned in the preliminary rounds that the third best player was not in the tournament since he had previous commitments.
David Madden could not participate due to some technical issue involving his National History Bee and Bowl. Apparently the NHBB uses the same Standard and Practices organization as Jeopardy! and he thought it would be too much of a conflict of interest.
With regards, I do think he is the third best player. He won a stacked Tournament of Champions over solid players like Joon Pahk, Tom Nissley, and Mark Runsvold. He also holds the record for money won in a single game. Madden won the second most amount of gamesm but he lost in the semi-finals of his Tournament of Champions. Going back to Roger, I think he made the correct call on the first day Daily Double. It was a second row DD, which usually means it is going to be an easier clue. Doubling up his 10,200 would have given him a large lead heading into FJ. With such a large lead he would have not had to make a big bet on the second day Double Jeopardy Daily Double.
Ken had some bad luck that prevented him from massing a lot of cash. Namely, he did not find a single Daily Double over the two days. Had he found one or two of those, he might have been able to take it.