In order to help Anthony Edwards, the Minnesota Timberwolves have been linked with Giannis Antetokounmpo and Kyrie Irving. But the franchise also knows they have to prioritize re-signing Ayo Dosunmu. The two-way guard became even more important to the team’s core with his playoff performances. However, that exactly makes him the mark for many suitors, including his former team, as per analyst Kendall Gill.

“I know it’s going to take a lot of money, but I would definitely try to go back after Ayo Dosunmu, as well,” Chicago Bulls TV analyst Kendall Gill said on the Mully & Haugh Show on 104.3 The Score tonight. “I know that Ayo, from my conversations with him this summer, would be open to it, but it’s going to take a lot to get him back. But that’s what I would do.”

Dosunmu reuniting with the Bulls is possible. The native of Chicago also played his college ball at the University of Illinois. So, the pull of hometown love could also be another factor. With over $52.8 million in cap space, according to Spotrac, the Bulls have plenty of money to play with in free agency. Conversely, the Wolves are nearing the second tax apron, and signing Dosunmu to a hefty new deal could further hinder them.

But his 43 points against the Denver Nuggets in the first-round series in the absence of Donte DiVincenzo and Anthony Edwards already proved why his signing should be a priority. Furthermore, DiVincenzo is expected to miss a massive portion, if not the entirety, of the upcoming 2026–27 season after suffering a torn Achilles. With veteran guard Mike Conley Jr. hitting free agency at 39 years old this fall, the Timberwolves find themselves in an incredibly vulnerable position.

They are left with very few reliable options to handle ball-handling duties alongside Anthony Edwards. Finch highlighted that the team relied far too heavily on Ant-Man to initiate the offense during the 2025–26 season, where he had a massive 31.4% usage rate.

“We definitely need another ball handler and playmaker. Somebody who can initiate the offense, take the load off of Anthony, get Anthony back to his natural best spot. It just put too much on his plate.”

Dosunmu has, meanwhile, shown that he can be a decent playmaker. He has averaged 3.6 assists per game in the regular season, but he had 9 assists in the Timberwolves’ 139-109 blowout loss to the eventual finalists, the San Antonio Spurs.

The Bulls, however, would need a veteran like Dosunmu this year. They are far from being contenders for the title and even farther from entering the playoffs as they head to the 2027-28 season. But the team is already turning over a new leaf.

New head executive, Bryson Graham, would certainly want to turn the Bulls back to their winning ways. He can use Dosunmu’s familiarity with the team under the new head coach, Tiago Splitter, to bring the rather young team together in hopes of making the playoffs. They have missed the postseason berth in the last eight of nine seasons now.

If Minnesota fails to re-sign Dosunmu, they will be forced to potentially shop assets like Julius Randle or utilize their No. 28 draft pick.

The Timberwolves are working on helping Anthony Edwards

Ayo Dosunmu is set to become an unrestricted free agent with a $7.5 million expiring salary. Teams across the league believe the 26-year-old will command a higher contract. NBA insider Jake Fischer reported that the Wolves are working “to try to hash out a new deal” to extend their partnership with Dosunmu.

Some reports suggest it could be a three-year deal worth around $50 million, putting him at roughly $16 million per season. That would put the Timberwolves right at the second apron line unless they make other moves in the offseason. Other teams like the Pistons, Bulls, and even the Pacers are looking to pounce on the Wolves’ tight situation.

Minnesota holds Dosunmu’s Bird rights, giving them the legal capacity to exceed the salary cap to retain his services. Even President Tim Connelly made it clear that their priority is to re-sign Dosunmu. He called the 26-year-old the “most important free agent” and was “pretty optimistic” about getting the negotiations over the line. Now, it truly comes down to whether the Bulls can manage the hefty pay to bring the player back they once drafted.