The Bulls have a clear starting point guard in Josh Giddey, but if they’re hunting for a better long-term fit, Ryan Rollins is the name that jumps off the page. Chicago should be looking hard at the Bucks guard now, while Milwaukee is in a spot where it may be more willing to listen.
That urgency matters because the Bulls are in a better place than the Bucks when it comes to building for the future. Both teams are in the middle of retooling, but Chicago has a healthier stash of draft picks.
Milwaukee, meanwhile, does not own its 2027 first-round pick, which removes any real incentive to sink this season. If the Bucks are going to move Rollins, the timing may be right for them to do it sooner rather than later.
Rollins has taken the long road to becoming a real NBA contributor. The 24-year-old was a second-round pick of the Atlanta Hawks in 2022 before being shipped to Golden State right away.
He never stuck with the Warriors, then landed in Washington in the trade that sent Chris Paul to the Bay Area and Jordan Poole to D.C. The Wizards waived him less than a year later, and he eventually signed a two-way deal with Milwaukee before breaking through last season.
Once he got his chance, he made it count. Rollins played in 74 games, including 67 starts, and averaged 17.3 points, 4.6 rebounds and 5.6 assists in 32.1 minutes per game. He shot 40.6 percent from 3-point range on 6.1 attempts a night, and he also made his presence felt on defense, finishing fourth among all NBA guards in total deflections.
At 6-foot-3 and 180 pounds, Rollins doesn’t have Giddey’s size. Giddey’s 6-foot-7 frame gives Chicago a different kind of option.
But Rollins brings something else: a 6-foot-9 wingspan, more defensive disruption, and a stronger profile as a shooter and off-ball threat. He isn’t the same level of passer or playmaker - Giddey is borderline elite there - but the Bulls would be adding a guard who better matches some of their bigger needs.
That’s where the fit gets interesting with Caleb Wilson and Matas Buzelis. Pairing a disruptive point-of-attack defender with the length and athleticism those two bring on the back line could give Chicago a nasty defensive foundation. Rollins also helps stretch the floor in a way Giddey does not, and that matters for a team trying to build cleaner spacing around its young core.
The financial piece makes the case even stronger. Rollins is on a $4 million deal this season, while Giddey is at $25 million.
Rollins is expected to turn down his $4 million player option next summer, but the Bulls should have room to sign him long term. His next contract should not top the average annual value of Giddey’s current deal, and Chicago can fit that on its cap sheet.
Milwaukee’s backcourt is crowded, too, with Tyler Herro, Brayden Burries, Kasparas Jakucionis, Kevin Porter Jr., AJ Green and the immovable contract of Gary Trent Jr. all in the mix. If Chicago is willing to put a lottery-protected first-round pick in this coming draft and a few second-rounders on the table, that should be enough to get the Bucks’ attention.
That’s the kind of move the Bulls need to make as they keep shaping a contender in the Windy City.
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Wilsons strong showing in the 2026 Las Vegas Summer League has already added a little extra heat to the Bulls future outlook, especially with Memphis forward Cameron Boozer on the other side. The two were college rivals, and while summer league can only say so much, it is the kind of backdrop that can give a matchup some immediate bite if both teams continue moving in the right direction. For now, the idea remains more seed than story, and the real test would come only if Chicago and Memphis end up crossing paths in the playoffs. [Read more 🡒]