I'm not going to say the 'experts' are wrong, etc, etc, etc. As far as I know, they could be right! However, for Badger coaches and players, it has to be a little irritating to continually be picked as the upset special each season! Last season, they were a popular upset pick and they ended up beating Belmont by 14. There is a reason Bo Ryan is 9-1 in opening round games.
Don't know much about Will Cherry, but I don't think he will get too many opportunities to take the ball away from Jordan Taylor, who is among the best in NCAA history in assist-to-turnover ratio.
Can Cherry play defense in the post? The Badgers haven't run the swing offense too much this season (or so it seems), but at close to 200 pounds, Jordan Taylor is one of the strongest point guards in the country and shows no hesitation in posting up other guards.
I am sure Cherry is a fine player and I am by no means trying to be disrespectful, but Jordan Taylor was a Second Team All-American as a junior and a Pre-Season All-American coming into this season. He has had somewhat of a 'down season', but has actually averaged over 16 PPG against Big Ten competition. I'd certainly give him the upper-hand without hesitation, but maybe I'm just biased
Edit: This is a really one-sided post as I don't know much about Cherry other than his accolades. Please rebuttal! I, like other Badger posters here, are still trying to learn more about your program!