This sort of thing happens on the Tournament of Books. Last year, Andrew WK actually selected Wolf Hall over The Book of Night Women—much to commenters’s chagrin.
The judges claimed that they hadn’t planned on Leithauser judging this particular match-up, which makes sense since how could they know this would be the matchup. (It’s arguable that if they had really wanted to engineer such a matchup, they could, since these were two of the strongest novels in the ToB.)
I was a little disappointed that Leithauser weighed in on the implausibility of a 21 year old arms dealer (which actually happened, according to an essay in Esquire I remember reading) rather than all the Inside Baseball music industry stuff.
I absolutely hated the last chapter of Goon Squad, which—was that the one that was supposed to ape David Wallace? And I really loved a lot of Freedom, though for likely perverse reasons; it depicted such a madcap trainwreck of a plot that it was like watching a high school version of Rocky and Bullwinkle. Still, I’m most disappointed with the length of Leithauser’s judgement. I know he’s not a writer, per se, but he is an artist. He should be able to express an opinion clearly. Maybe he should have written a song about it, instead.