I believe we're all agreed that the questions, ESPECIALLY this season, are a lot harder than they were in Regis' day, so that claim is mostly moot at this point. Leszek is far from an idiot. He'll play the hand that's dealt him.
The questions on the daily show have always been harder than those of the primetime version, as least in my own estimation, and the piece in question is from November, 2000. (There's references to History IQ and the Gold Pocket online game.)
http://www.nytimes.com/2000/11/05/magazine/the-know-it-alls.html?pagewanted=all That's a link to the article, and I apologize because I don't know how to change the text of a hyperlink.
I'm particularly happy that the show seems to have widened their net in having on players who can handle the tougher material because there's no reason for those top prize figures to be displayed if no one is going to reach them. I hope he does well because I enjoy seeing those top-drawer questions and I have no reason to root against him or wish him poorly.