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Tim Connelly speaks more on failed 2024 Rob Dillingham trade

Nobody bats 1.000 in the transactions log.
Dec 17, 2025; Minneapolis, Minnesota, USA; Minnesota Timberwolves guard Rob Dillingham (4) dribbles the ball against the Memphis Grizzlies in the second half at Target Center. Mandatory Credit: Jesse Johnson-Imagn Images
Dec 17, 2025; Minneapolis, Minnesota, USA; Minnesota Timberwolves guard Rob Dillingham (4) dribbles the ball against the Memphis Grizzlies in the second half at Target Center. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

It was nearly 23 months ago where the Minnesota Timberwolves didn’t have a first round pick (theirs was dealt away in the Rudy Gobert trade). The front office saw a player they liked in the 2024 draft in Rob Dillingham though. They decided to give up a 2031 first round pick and the right to swap 2030 first rounders picks to the San Antonio Spurs in exchange for the eighth selection in 2024.

The fact that Dillingham was traded to the Chicago Bulls a little more than 19 months later is an indicator that the trade didn’t really pan out (although the deal did net the Wolves a wonderful player in Ayo Dosunmu). President of basketball operations Tim Connelly was asked about the 2024 deal in his exit interview.

“I think we took a swing on a guy, a young player we really liked.” Connelly said. “Didn’t work out here like we had hoped. I think Rob’s going to have a heck of a career, but you have to be creative, not just with the aprons, but we have to be creative with some of the market dynamics in the places we’re in…if we mess up, we’ll mess up loudly.”

When in apron land in the NBA, it can take creativity, as well as risks, to try to improve the roster.

Rob Dillingham was looked at as the successor to Mike Conley

First off, Connelly has made great efforts in improving the roster throughout his tenure. No, it has not yet resulted in the Timberwolves’ first-ever NBA finals appearance. It is still their best era, in terms of playoff success, in team history.

No front office is ever going to have a 100 percent success rate in its transactions. Even the incredible Sam Presti of the Oklahoma City Thunder traded for Gordon Hayward at the 2024 trade deadline, who proved to be finished and retired after the season.

The idea that Dillingham could become a much-needed addition for the Timberwolves was understandable. Mike Conley was regressing as he aged, and Dillingham provided a succession plan. Sure, he was a smaller guard, but shooting is so vital in today’s NBA.

Dillingham knocked down 44.4 percent of his 3-point tries during his one year at Kentucky. Unfortunately, in 84 games for the Wolves, he made just 34.4% percent from beyond the arc and only 42% percent of his shots from inside the arc.

He’s still just 21 years old. Players have finally figured it out in the league many years older than he is. As a team with championship aspirations though, Minnesota couldn’t afford to wait.

Connelly was well aware that being an apron team made it rather difficult to execute a trade for a star point guard in hopes of upgrading the team.

Why not look towards entering the draft and taking a guard you love? No, it didn’t work out, but he was still seen as having trade value by the Bulls. He was part of the package for Dosunmu, who is a free agent, but hopefully will remain with the club.

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