It's a joke that Bo Ryan won COY. Bo specializes at taking advantage of the weaker teams in the league and beating up on them, and the schedule helped him do that. Surprising IU in Bloomington when they weren't thinking they'd have a tough game, a miracle home win over UM, and OSU didn't care enough to show up against you in Madison - those are your best wins on the season, and that gives you something to crow about?
In 2009, the circumstances were similar as MSU won the title outright, and Matta was able to get OSU to a #4 Big Ten finish and NCAA tourney berth in spite of coming off an NIT season and losing David Lighty to injury early in the season. They had a couple good freshmen but they also lost what were their 3 best players off that NIT team in addition to having to redshirt Lighty. Of course, no one thought Matta should win COY because he didn't deserve it more than Izzo even though Matta did a good job - I guess when you're Wisconsin and no one thinks you're any good, being halfway decent is an accomplishment.
When you haven't won the Big Ten in several years or advanced past the S16 in nearly a decade, and when you start off the season losing at home to freaking Virginia and against Creighton and fall out of the top-25, you fall off the radar pretty quick and nobody has you circled on their calendar. It's harder when everyone wants to play you and everyone's gunning for you like teams were against IU, MSU, OSU and UM. The coaches of IU, MSU and OSU at least ALL deserved to win over Ryan. Crean has taken IU a long way from where they were a few years ago, clearly it is a major accomplishment for his team to win the league outright this year. You think it's easier to replace Gasser and Taylor or Buford and Sullinger? How about 2012 league POY Draymond Green? MSU and OSU both played much tougher Big Ten schedules and lost a lot better players, and teams actually want to play against them.
Nobody wants to play Wisconsin because they play such a boring style and it isn't that good of a win. Once the tourney rolls around and teams actually won't overlook you, you struggle and get bounced in or before the Sweet 16 every year because you don't have great talent compared to the top teams in college basketball. Hope you enjoy another year where UW finishes 4th and doesn't have a deep tourney run. At least you have Bo's winning percentage and streak of top-4 finishes to help you sleep at night. And of course Bo's recruiting is so mediocre that you practically never lose anyone early to the NBA so you can plan on being "consistent" again next year. Congrats!