Rob Dillingham is the Wolves’ Most Pain-Free Way to Improvement

The trade machine is abuzz, and keeping the band together remains a possibility, but for any of those things to work, a 20-year-old sophomore needs to take the next jump.

Shortly before 8:00 in the evening, roughly a year ago on June 26, a bat signal was put in the air that dynamic Kentucky Wildcats guard Rob Dillingham was not going to end up on the San Antonio Spurs.

That night, the Minnesota Timberwolves made a surprising trade on draft night, sending a 2031 unprotected first-round pick and a 2030 first-round pick swap to the Spurs in exchange for the eighth overall pick that San Antonio used to select Dillingham for the Wolves.

Perhaps the biggest wildcard but most exciting player in the draft, Dillingham, was heading north to prospectively share a backcourt with Anthony Edwards and join the Timberwolves, fresh off their first Western Conference Finals appearance in 20 years.

Owner of an electrifying highlight reel during his time in Lexington and in possession of dynamic ability with the ball in his hand to both create and score, it was immediately projected that the Wolves had their backcourt of the future.

But 10 months and five more Western Conference Finals games later, the Wolves once again proved not to be all that close to a championship despite another prolific postseason run.

A symptom of the skill gap in their five-game funeral? 15 collective minutes for their top 10 pick in Dillingham, running the floor during garbage time in three of the five games. Thought to be an immediate difference maker and future backcourt piece next to Ant, his first year didn’t particularly shake out the way anyone thought it would, and I think he would be included in that contingent.

But one series away from reaching the first NBA Finals in franchise history, something that seemed like a real possibility, the fantasies of the Larry O’ Brien trophy for everyone were quickly replaced with mental math on salary matches and the most accessible trade machine tools available.

Dillingham has been a fixture of much of this talk. Seemingly reduced to a placeholder as a young player serving as a means to a better end in trade conversations in the mind of the internet, I want to run through the thought exercise that, with an offseason of improvement, perhaps the next level for the Wolves exists on their own bench.

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Vincent Carchietta-Imagn Images

Nothing According to Plan

“We plan, and then you get a call and the plans are out the window,” Timberwolves President of Basketball Operations Tim Connelly said at exit interviews that were held shortly after the Wolves’ season came to an end.

In reflecting on a trade that was made 48 hours before the opening of training camp to send out Karl-Anthony Towns to the New York Knicks while bringing in Donte DiVincenzo and Julius Randle, Connelly opened up more about the ripple effect it had on the rest of the roster.

Not only was an experienced, starting-caliber guard in DiVincenzo brought over as a product of the seismic, last-minute move, but it also shook up the idea of what the Timberwolves had for both of their first-round draft picks under the current roster construct.

“When you have the opportunity to be aggressive, be aggressive,” Connelly said. “But obviously, the team is constantly evolving…I’m pretty into the idea of just having as many good players [as possible]. I don’t think you can get too dogmatic with roster building, because you can get a call that can change that dramatically, and the more good players you have, the more good problems you have.”

Jeff Wheeler | The Minnesota Star Tribune

One of those good problems was the undersized Kentucky guard. Slated for a surefire rotation spot with Towns on the roster as the season neared was a role that quickly blew up with the trade taking place.

The good? Promising flashes in games where the Wolves needed it, including an early-season 12-point, seven-assist masterpiece off the bench in an NBA cup qualifying game. Dillingham led a comeback in masterful fashion, showing exactly why he was a top 10 pick just five months prior. Flashes like this took place throughout the season when He was called into action.

The problem? The angst that came with sitting on the bench for the majority of the season, whether deserved or not, with more seasoned, win-now players ahead of him. It’s easy for others to take notice of that, especially someone like Anthony Edwards, who also experienced spotty playing time early in his career.

“[Rob] said something that stuck out to me the other day, he said, ‘You think I’m gonna hurt y’all if I get out on the court? You think I’m gonna hurt y’all?’ He was like, ‘No, I’m gonna help,” Edwards said after the Wolves win in Madison Square Garden in January, referencing Dillingham’s frustration with not being able to get on the court. “You can’t really say nothing back to that because the confidence is there and he done showed it.”

There’s no question Dillingham showed it on a multitude of occasions. But becoming consistent and turning into a 10-12 point-per-game scorer is what can take the Wolves from a Western Conference Finals washout to having another gear.

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Photo by AAron Ontiveroz/The Denver Post

The Next Step

Let’s start with what the Wolves were blatantly missing in a series with the Oklahoma City Thunder, which proved not to be all that close.

• An off-guard that could take pressure off of Anthony Edwards
• An additional ball handler quick enough to collapse a defense and distribute
• The ability for an additional floor general to be able to create their own shot

Terrence Shannon Jr. has a bright future ahead of him and was able to demonstrate some of those things immediately, but much of that can come in the form of the development of Dillingham.

Too often are young guys are written off quickly in the NBA, especially guards who take time to learn the game at NBA speed and diagnose defenses at a rapid pace. Shannon, at 24 years old, has a leg up on how much basketball he’s played. At 19 heading into the season, Dillingham hasn’t scratched the surface. For a team that’s built on the development of its own draft picks, an in-house solution that can turn into the answer for all three bullet points above can come to fruition. Too many trades using Dillingham as the “young player” placeholder in trades to speed up the improvement of the overall roster and waving the white flag on the 20-year-old guard as an asset loss seem to be premature.

So, where are the immediate places he can improve?

Being shot-ready

Dillingham was 30 percent this season on catch-and-shoot threes and 36 percent on pull-ups. With someone who draws as much gravity on the floor as Edwards does, being able to spot up and knock shots down is important. Edwards learned it quickly playing next to Karl-Anthony Towns, and now others who are threats to break people down off the dribble need to do the same next to him.

“I think he’s got to round out his shot…he’s got some inconsistencies right now,” Timberwolves head coach Chris Finch mentioned in exit interviews. “he’s got to be ready to knock [catch and shoots] down at a pretty high clip.”

When Dillingham was at his peak effectiveness, he was able to add the outside shot to his game as a weapon to complement paint penetration, making defenders unsure of his next move off the catch, and therefore giving himself space to operate on the floor.

Simplify the offense

Oftentimes, early exits from games for Rob stemmed from too much dribbling and not enough quick ball movement. When the latter happened, the Wolves played at an electrifying pace, which led to fans demanding more minutes.

When the former happened, a logjam of a good old-fashioned game of “your turn, my turn” happened.

“Some of his turnovers are easily correctable,” Donte DiVincenzo said earlier in the season.

“I keep telling him to slow down, especially when it’s in the two-man game,” Rudy Gobert added. “I’m going to give him an advantage, and all he has to be able to do is read the defense.”

What say you, Mike Conley?

“I’m just trying to be in his ear and preach to him how important the things are that he can pick up from in the moments he’s not playing,” the veteran point guard said, even before Rob was able to get more consistent rotation minutes. “Learning our plays, learning our schemes, learning other teams’ schemes.”

Simplify, simplify, simplify. When Edwards came onto the scene as a rookie under the recently-hired Finch at the time, the simplified offense in coming off of motion and getting downhill led to profit for the young, physical guard.

From Rob’s standpoint, keeping defenders guessing with his first step and quick ball movement are easy ways to be able to put pressure on a defense and take some added work off of the others around him (something Shannon was able to do right away with effectiveness).

Other obvious areas for improvement are defensive tenacity and physicality, which can come from putting more weight on his frame.

Finch, along with others in the organization, talked throughout the season about Dillingham’s defensive effort improving and how important it was for him to not be a “zero” on that end of the floor. It was palpable, and something that kept him on the cusp of the rotation, something that other young players under Finch haven’t been able to say during their career with the Wolves (Jaylen Nowell, anyone?).

The pounds will come. If improvements on the margins can happen, the minutes should too.

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I don’t typically make these arguments. The flashy trade, especially for a living legend being on the table, is tempting.

But a point in time comes where you see a clear blueprint working and become hesitant to stray from it.

For the Wolves, it’s been to develop what you already have. In this case, what they need can be (and I want to stress that) accomplished with a 20-year-old guard who showed many times throughout the season that he can be that. The highs were high, and there were plenty of lows to be expected from a rookie. But in the likeliness that the Wolves round up a similar roster from last season and try to make another run under a crippling CBA that emphasizes young players and flexibility, Dillingham turning into a 10-12 point per game scorer could prove to be the jump that can take the current roster to the next level.

A pick swap and unprotected first-round pick past 2030 shouldn’t be discounted in the move they made to bring the young guard in just a year ago. You don’t make that move to simply give up after a season.

In this case, I think you should double down.