Timberwolves face a crucial Rob Dillingham dilemma

It's a pivotal second season for Rob Dillingham.
Minnesota Timberwolves v New York Knicks
Minnesota Timberwolves v New York Knicks | Sarah Stier/GettyImages

It was evident in the 2024 NBA Draft that the Timberwolves really wanted Rob Dillingham. They traded the Spurs a 2031 first-round pick (as well as a 2030 option to pick swap in the first round) in order to acquire the eighth overall pick. Dillingham’s rookie season was littered with inconsistent playing time and inconsistent production.

While he’s still just 20 years old (turns 21 on January 4), Dillingham is entering a pivotal second season. Chris Finch has a dilemma on his hands as to whether Dillingham is ready for extended playing time on a team with championship aspirations.

Slow start for Rob Dillingham in preseason

With Mike Conley turning 38 today (October 11), many expect his minutes to decrease in 2025-26. Looking at their roster, it would seem as if those minutes could go to Dillingham.

Unfortunately, the 6-foot-1 point guard hasn’t really stood out in the Timberwolves’ first three preseason outings. Dillingham is shooting a miserable 5-20 from inside the arc (much more respectable 3-8 from beyond it). The 18 assists are nice, but he has also turned it over eight times.

Dillingham has also been outplayed by Bones Hyland in the preseason (at least in the first 2 outings). Hyland barely played for Minnesota after joining them last February. He re-signed just before training camp, and he wasn’t expected to be a threat to Dillingham’s playing time. Now, Hyland is at least making Finch take a harder look at that possibly occurring.

There’s also a growing belief that Donte DiVincenzo could begin the year as the starting point guard. Finch trusts Conley, so it’s doubtful he would exit the rotation if that were to happen. Where would that leave minutes for Dillingham?

Is Dillingham a sure thing to be in the opening night rotation?

Not playing Dillingham though, would come with the risk of shattering his confidence and/or trade value. If the point guard position becomes a clear need during the season, it should surprise no one if Minnesota looks to acquire one. Dillingham potentially could be included in a deal.

It’s never easy trying to give valuable minutes to youngsters at the same time you’re trying to win a title. Dillingham has three preseason games remaining to instill more confidence that he should be a part of the rotation. We are just 11 days away from the Timberwolves’ regular season opener, and it’s unclear if Dillingham will receive non-garbage time in that game.