Rob Dillingham's play has been one of the disappointing aspects of the Minnesota Timberwolves' season. The second-year guard has failed to take the next step that was widely expected of him. Dillingham is averaging just 10.6 minutes, 3.8 points, 1.3 rebounds, and 1.9 assists on 34.2/29.6/77.8 shooting splits. His points, assists, and efficiency from the field have all declined. Minnesota's offense is also 15.3 points worse per 100 possessions with Dillingham on the court.
Frankly, it looks like Dillingham has lost a lot of confidence, and there have been very few signs that he looks like the promising point guard the Wolves traded up to draft. With Dillingham not progressing and Mike Conley continuing to decline, it's widely believed that the Wolves will pursue point guard reinforcements before February's trade deadline.
Where does this leave Dillingham, though? He certainly could be a trade candidate, but giving up on a second-year guard feels harsh, and despite being a lottery pick in 2024, his value is likely not high. However, keeping him around in a limited bench role would essentially be punting on his development. With Terrence Shannon Jr. injured, it looks like Dillingham has one last chance to prove himself as a worthy rotation player in Minnesota.
As the trade deadline quickly approaches, the Wolves are left with a Dillingham problem that has no easy solution.
The Timberwolves are in a tough spot with Dillingham
If Dillingham is the centerpiece of a trade, it will be for a role player and likely a point guard. The idea of a Dillingham-Jose Alvarado trade, for example, could help the Wolves reach their ceiling this season. Nevertheless, it's possible, perhaps even likely, that the Wolves would have to include draft capital to make this deal work.
I don't think this is the best way to look at things, but I'm sure it's not lost on Tim Connelly that he traded two future first-round picks to draft Dillingham. As such, trading more draft capital to land a role player could make Connelly apprehensive.
Let us not forget his vision was for Dillingham to be the point guard of the future next to Anthony Edwards. I'd also be willing to bet that while Chris Finch may have lost hope in Dillingham, Connelly still believes in him. When making a trade like this, there's also the fear that you're giving up on a young player too soon. It wouldn't shock me at all if Dillingham thrives with a change of scenery.
Now, Dillingham being dealt in a bigger deal for a star PG would lessen these fears for the Wolves. The trouble is, none of the possibly available star-level point guards is a clear fit, and they all have significant risks. To make a deal work for such a player, the Wolves would have to include one of their bigger contracts and better players.
I've expressed my belief that it wouldn't be worth it for someone like Ja Morant or LaMelo Ball before, and I don't know if the Wolves are truly eyeing one of these stars. So if the Wolves don't make a big trade like this, they may settle for a smaller deal for a point guard or simply stand pat. Where does this leave Dillingham, though?
Overall, Dillingham's future with the Wolves is quickly becoming murky, and there's no clear solution.