I was in high school for the Final Four team and even then I thought I had the right attitude to appreciate every second of that team because we might not be back for another decade. To not even make a Sweet 16 since that time has been beyond everyones worst nightmares. These events might not all be chronological, but I was thinking of all the different things that have gone wrong or been done wrong since '97.
Courtney James dismissed- The year following the Final Four was Sweet 16 good at minimum with James on the team. Charles Thomas was another piece that would have helped. The two bigs of Sanden and Loge who were fairly highly regarded not panning out was another blow here.
Pioneer Press leaking the "Scandal"- It seems forgotten that the Pioneer Press decided to publish this "shocking" "scandal" just in time for the Gophers NCAA first round game against Gonzaga. Gophers only trailed by 2 with less than 2 minutes left. They easily could have went to the Sweet 16 that year. Instead Gonzaga goes on a run to the Elite 8 through the path Minnesota would have had AND that leads to Dan Monson becoming the Gophers coach.
The sanctions and reaction to them- The administration decided to fall on the sword and act like something horrible had happened here. The fan base accepted that reaction. The correct response was "F you NCAA, we're not Cleveland State". Instead a bunch of people pretended like Clem Haskins was the devil and there are still people that like to pretend like the '97 season wasn't legitimate.
Hiring Dan Monson- It's hindsight, but he wasn't a good coach. You couldn't blame the choice at the time especially given the sanctions. That said, it certainly wasn't the right choice and people were paid to make a better one.
Dismissing Pryz- I think this was an overlooked one. Pryz got dismissed from the team for relatively minor stuff (he was passing classes, just not attending every one). The really tough thing here is people cheered Monson for this. I think this was looked at by the administration as another sign that they did the "right" thing and Monson was the "right" guy.
Burleson game- If Monson was ever going to get it going at Minnesota it was at this point. He had an NCAA bid locked up here and they absolutely choked it away in the waning minute at home against Illinois. Someone with a better memory with me could expound on this, but I feel like this might have been the turning point from the Barn being a tough place to play to it becoming a place where miracles consistantly happened for the other team.
Monson spurning Washington- Monson was offered the job at Washington, might have even accepted it, but changed his mind. Could have been done with his tenure years earlier.
Vincent Grier- If Vincent Grier wasn't great in his first year as a JUCO transfer, Monson is gone as that lead to his one surprising NCAA tournament team. Somehow a team with Aaron Robinson/Jeff Hagen/Brett Lawson/Vincent Grier went further than Rick Rickert/Jerry Holman/Mike Bauer.
Maturi "firing" Monson- Again we go through a complete lame duck season because Maturi fails to fire Monson after an NIT loss. He'd be fired early the next season after some embarrassing losses.
Not letting Royce and Trevor play- The Tubby era was off to a good start. An NCAA team in year 2 was returning basically everybody and adding Royce and Trevor. Maturi decided that neither could play. They still are an NCAA tournament team. That's a clear Sweet 16 team or better with both and had a good chance with one of the two. I have heard these decisions along with Maturi not following through with the practice facility really angered Tubby.
Al Nolen academically ineligible- I am not aware of another starter on a Big Ten team being decared academically ineligible during the season for many years prior to Nolen and in the time that has past since. Must just be a coincidence that it happened at Minnesota...
Norwood Teague/Mike Ellis/Villa 7: The two sexual predators pushed Gopher basketball to new lows. They tried for Brad Stevens and Shaka Smart. They tried (and came close) for Fred Hoiberg. They angered some influential Gopher boosters with how they handled Flip Saunders after striking out on their preferred home runs. They decided if they couldn't have a home run, they were going to create a second Shaka and hired...Richard Pitino?
Reggie Lynch: I am not sure how to put this without possibly slandering somebody. If what appears to be true about Reggie Lynch occurred/was known at Illinois State, Richard Pitino is fired after 4 years. If the Lynch stuff was known during his redshirt year at Minnesota, Pitino is gone after 4 years. If it disrupted Pitino's 4th year, Pitino would have been gone after 4 years. Instead Lynch helps Pitino to by far his best season which leads to a contract extension and immediate disaster. If for some reason all of the allegations about Lynch are not true, then his dismissal from the team was still a huge turning point.
Akeem Springs injury: That team was playing its best ball and Springs goes down late in a Big Ten tournament game costing us a chance at a tournament title. We arguably should have beat MTSU in the NCAA tournament anyway, but Springs had a very important skillset (including intangible/demeanor) that team didn't have a replacement for. There was certainly a chance for a Sweet 16 with or without Springs that year given the Gophers draw, but odds were far greater with him.
Holding on to Pitino far too long: This is all on Coyle and is so recent it does not need to be discussed. We've been coached by Monson/Pitino for 16 of the ~25 years or so we are talking about. With competent leadership Pitino is never hired (maybe Monson isn't either?) but even assuming both somehow getting the job, competent leadership doesn't leave them in place for more than 8 years combined. There should have been at least one more hire (depending on success of said hire) during this time frame.