MINNEAPOLIS — Tim Connelly’s challenge at this year’s trading deadline was to walk two separate paths with equal purpose.
First and foremost, the Minnesota Timberwolves president of basketball operations had to diligently explore what would have been a massive, multi-team trade for Milwaukee Bucks superstar Giannis Antetokounmpo. As the two-time MVP’s future in Milwaukee became a central talking point around the league, Minnesota got word that Antetokounmpo was open to the idea of teaming up with Anthony Edwards, team and league sources told The Athletic.
It is not often that a player of that caliber expresses an interest in coming to Minnesota, so the Timberwolves had to explore as many scenarios as they could to see if it was realistic for them to pull off.
At the same time, Connelly had to keep his eye on the guard/wing market to bolster a bench unit that has been one of his team’s biggest weaknesses this season. At 32-20 and in fifth place in the Western Conference, just a game out of third, the Timberwolves have shown that they can beat elite teams. Coming off of back-to-back Western Conference finals appearances, they have proved to be a team worthy of investment.
When it became clear to the Timberwolves that there was no deal to be had with the Bucks, Connelly quickly pivoted to fill a NAW-sized hole on the roster.
The Wolves acquired Ayo Dosunmu from the Chicago Bulls in a deal that sent Rob Dillingham, Leonard Miller and four second-round picks to Chicago, league sources told The Athletic. Forward Julian Phillips is also coming to Minnesota.
Dosunmu is set to become a free agent this summer. But this deal gives Minnesota his Bird rights, meaning the Wolves can go over the cap to sign him to a new deal and retain him going forward.
Dosunmu, a hard-nosed 6-foot-4 combo guard who just turned 26, is averaging 15.0 points and 3.6 assists while shooting 45 percent in his fifth season with the Bulls. He can defend multiple positions off the bench. If that sounds like someone familiar to Wolves fans, that is exactly what they are hoping.
All season, something has been missing in Minnesota. A bench unit that was among the best in the league last season had to say goodbye to Nickeil Alexander-Walker last summer, and the absence of a long, defensively versatile combo guard who could shoot it has been perhaps the most glaring weakness of an otherwise promising team.
In sending out Dillingham and Miller, Connelly was willing to move two young players who have been buried on the bench to a rebuilding team that may offer more opportunity to play.
The Dillingham part of the equation stings. Connelly traded a future first-round pick swap and an 2031 unprotected first-rounder to select Dillingham eighth overall in 2024. He believed Dillingham could be the team’s point guard of the future, but he never earned head coach Chris Finch’s trust.
Dillingham averaged just 3.5 points, shot 33 percent from the field and has been out of the rotation since Dec. 19. On the few occasions he did play, Dillingham appeared to have lost most of his confidence while looking over his shoulder every time he made a mistake.
From Finch’s point of view, he couldn’t afford to give minutes to a 20-year-old project on a team that was trying to take the last step and make the NBA Finals. He preferred 38-year-old Mike Conley and journeyman Bones Hyland with the the second unit instead.
Miller played even less. He was taken in the 2023 second-round pick appeared in just 49 games over three seasons, all in garbage time.
The four second-round picks heading to Chicago are as follows:
- 2026: least favorable between Denver and Golden State
- 2027: via Cleveland
- 2031: most favorable of Minnesota or Golden State
- 2032: most favorable of Phoenix or Houston
Connelly waited as long as he could to see if the Bucks would engage on an Antetokounmpo deal. But as The Athletic reported Monday, there was real skepticism within the team and around the league that Milwaukee was truly ready to sign off on trading the face of its franchise. With no first-rounders to trade, the Wolves would have had to move a bevy of players, likely including three of Jaden McDaniels, Julius Randle, Rudy Gobert and Naz Reid to acquire the picks to entice the Bucks into making a move.
They explored numerous avenues, but never engaged the Bucks on anything of real substance, team sources said. By Thursday morning, it became clear to the Wolves that Antetokounmpo wasn’t going anywhere.
It was clear by Wednesday night in Toronto that the rumors were starting to weigh on the players. Most understood that a deal to get Antetokounmpo likely meant a large portion of the roster would be heading elsewhere.
New owners Marc Lore and Alex Rodriguez were intrigued by a potential blockbuster, team sources said, but they were not fully convinced that breaking up the young core of Edwards, McDaniels and Reid, or parting with rookie Joan Beringer, was prudent. Similar conversations and debate played out inside the front office and coaching staff.
Ultimately, the Wolves were never truly forced to make that decision.
While they made clear to the Bucks that they were interested in discussing the possibilities, team and league sources said, Milwaukee never reciprocated to a level that elevated the discussions before pulling Antetokounmpo off of the market on Thursday.
A good portion of the fan base was nervous about parting with favorites like McDaniels and Reid for a 31-year-old with a history of soft tissue injuries, even if that veteran was one of the best players to ever play in the league.
Now, the Timberwolves can breathe a little bit. They have retained their young core and also have Randle, who was dominant in the first two rounds of the playoffs last season and Gobert, who is pushing for a fifth Defensive Player of the Year, surrounding Edwards. With Dosunmu on the way, the bench will be deeper and tougher.
Will it be enough in the demanding Western Conference? That remains to be seen. But the Wolves needed to upgrade the bench to truly give themselves a chance.
Lore and Rodriguez signed off on it and Connelly executed it, making Edwards’ words after a 128-126 win in Toronto on Wednesday night prophetic.
“Everybody’s mind is racing thinking this is gonna happen or that’s gonna happen,” Edwards said. “I told them, ‘Everybody here is secure and safe. Let’s just play.’”