When you are looking at 2-10 as a real possibility, then almost everything is a failure.
Go to the 10 minute mark. If what is said is true, the culture of the program is pretty much ruined. This "corporate" approach may work in a football factory like Georgia or Alabama, but it will never work at schools like Wisconsin, Iowa, Illinois or Minnesota.
It's also time for Wisconsin fans and the podcasters to stop crying about NIL money.
https://247sports.com/longformarticle/college-footballs-top-50-programs-ranked-by-nil-efforts-235181311/#2472519
If that is anywhere near accurate, it shouldn't be a problem. Occasionally Wisconsin would pull in a top 20 recruiting class, but more often than not, they would sit in the 26-35 range and were still very successful with those types of classes. If they are top 30 in NIL resources, there is no way they should get completely bullied off the field by Iowa.
So I had looked at all the incoming transfers from this last off-season. To me the results seem pretty lacking. I'd argue that the only "difference-maker" in the group is Mason Reiger, and it's not like he's pushing for first or second team all-Big 10 honors. They picked up many DLmen, a starting CB, David Heinzen who crapped out at LT and is now in the interior. Billy Edwards has a very small sample size so far, but when he's been on the field he hasn't even been able to complete 50% of his passes (not to mention, his transfer has many people in Madison running to grab the nearest barf bag).
So generally the first season of high school recruiting is lost, considering that, Fickell has had two recruiting classes so far. With as terrible as this team is, one would figure that a bunch of those redshirt freshmen and true freshmen would be pushing for playing time. And who has been the best player out of those two classes so far, Dilin Jones? Jones hasn't looked like anything really special.
As far as the coaching staff, Tressel's 2-4-5/3-3-5/4-2-5 seems like it was built for Conference USA/MAC football. It sure didn't seem to work when they got to play big-boy Iowa. I know I'll get ripped for saying this, but I've heard enough criticism about Grimes gimmicky play-calling to think that he is a downgrade from Longo. I was super high on Blazek, but the results there have been terrible. You go through the list of position coaches, and most of them seem pretty young and inexperienced, and the guys who have been around for a long time have most of their experience coaching at Grand Valley State. Paul Haynes is one of the few guys that has a real solid resume coaching at the higher levels. I'm not saying you need a staff filled with old guys, but Wisconsin definitely seems to have a lack of higher-level coaching experience on their staff.
So pick one main reason? Fickell has turned this program into a complete mess. If what Collin Wilder said in the above video is true, they have definite culture issues. Add in the fact that the coaching staff doesn't seem to be all that great and they clearly are not getting in good enough players, it's no surprise that 2-10 is a real possibility.