I think that's what turned me off when he was a Chaser: he leaned into the villain role way too heavily. Ken and Brad seemed to have fun with it, Mark continued his role from the UK and GSN versions, but it really felt like James was self-aware for all the wrong reasons.
Honestly, he was my favorite American Chaser of the original three for that very reason. Ken and Brad were good Chasers, gameplay-wise but didn't seem to have the kind of competitive edge that makes the games feel more compelling. James better understood the assignment.
One of the (several) issues with the clock seasons was that the clock starts as Meredith reads the choices, and you also accrue that time for Q15 throughout. From what I recall, if Alan had decided to stop at $50,000 instead of speedrunning his turn as a pilot for Game Shows Done Quick, he would have been sixth in line for the Group of Ten playoff which would be a much better way to win the million dollars. Such is life. As much as it comes off as rude or brusque and you may dislike it, it is a perfectly valid way to play.
And this is why I didn't mind the guy. Everyone knew that time banked was a tournament qualifier criteria, so the fact that he was willing to be "the guy who constantly interrupts our sweet Meredith" in pursuit of this goal was worth a tip of the hat to me.
I really didn't have anyone I explicitly rooted against, but one of the only times where I clearly remembered going "hmph-serves them right" was Kati Knudsen. I just recall Regis, begging within his legal right to do so as emcee, for her to take the $250k. Later hearing that she spent an ungodly amount of actual time in the chair contemplating that question removed all but the baseline amount of empathy I had for her. Still sad for her that she lost the money, but all things considered, it was a foolish gamble.