James made Ken play (and wager) differently than he did when he had his winning streak.
James took big risks, and sometimes paid off big (but not the tournament). There were a few times that Ken had to risk it all with the Double Jeopardy questions, and without James there, he probably would not have.
I would say poor Brad, because he did not have a good showing this time, he was just playing against 2 amazing players, but then "poor" Brad only won $250,000 for this appearance and a total of over 4.6 million dollars overall.
So yeah, poor Brad.