Coming off a uniquely discouraging loss to High Point in the NCAA Tournament’s Round of 64, Greg Gard and the Wisconsin Badgers don’t have time to lick their wounds, as the transfer portal madness will be upon us before you can say “Still No Sweet 16 Since 2017.”

With this in mind, here are my very early best guesses for the chances of the Badgers retaining their guys. Part 2, which will cover rotational players, will drop soon.

Let’s dive right in here with the Badgers’ trickiest retention target. I want to be up front with the fact that I have zero insider information on this, but I’ve talked to enough folks who cover the program to have a distinct vibe that he’s quite possibly gone. Illinois, Michigan, and Michigan State have been the most frequently linked suitors for a player who grew up in Detroit and whose father played for the Illini.

Coming off a season with many highs, but a few obvious regressions, especially on defense—along with admitted “struggles” off the court—it’s natural to wonder if Blackwell might be looking for a fresh start (and bigger paycheck).

The fact that there will be more money on the table elsewhere (I don’t think it will be the NBA) doesn’t help the Badgers’ chances. But my vibe is that Gard, the coach who believed in Blackwell when none from other Big Ten programs did, will give Blackwell a very fair offer with a raise and let the chips fall where they may.

High-scoring wings with middling defense are easier to find in the portal than top-quality point guards or bigs with the diverse skills of the player in my next evaluation. Chances of Retention 50%.

Given his premium skill set and room for growth, there’s a good argument that Winter should be the Badgers No. 1 priority for retention. It’s also a fact that he likely has more to prove before an NBA squad will use a pick on him, although I suspect workouts and testing would only help his cause.

Winter has always struck me as Minnesota Nice and profiles as a quintessential Badger. But I felt similarly about Chucky Hepburn before he surprisingly bolted for Louisville before his senior year, so nothing can be taken for granted.

Winter declining to commit to a fourth season in Madison 20 minutes after losing to High Point has been overblown. He was distraught and coming to grips with a cruel and premature end to what was looking like a special March run.

So, I will cut him some slack here. My vibe is that we’ll see Winter back with the Badgers in ‘26-27. Chances of Retention: 70%.

Rapp’s progression on both offense and defense as the season progressed was incredibly encouraging, and his commitment to another year in Madison immediately after Wisconsin’s loss to High Point was music to fans ears.

For the same reasons why we shouldn’t put too much of our hopes and dreams into what Winter said or didn’t say postgame on Thursday, I’d caution you to take Rapp’s Badgers pledge as written in pencil.

While I think he’ll be back, there will be suitors for Rapp’s skill set, and he will be getting a sizable raise. Gard will need to work a bit to lock him down. Chances of Retention: 80%.

Like Rapp, the sturdy Lithuanian big who appears older than his actual age made impressive strides as the season went along, ending up as a solid 5/5 guy with a few notable high points, including torching an elite Michigan squad from deep on the way to college basketball’s most impressive victory of the season.

But his defense has a lot of room for growth, and his offense can also improve, so my guess is that both aspects of his game will be nurtured in Madison, where he was a valuable starter as a true freshman, a rarity.

While he’ll surely have a market in the portal given his age and inside/outside talents, it won’t be nearly as robust as for other Badgers. Being from Europe makes it a bit murkier, but I feel uniquely confident he’ll be back in Madison. Chances of Retention: 85%.