The Minnesota Timberwolves were hosting the Houston Rockets, and after a tranquil start to his rookie season, Dillingham was finally starting to cook. He had played just 47 minutes and scored 16 points in the Timberwolves’ first 15 games of the season, taking a backseat to the veterans on a team with championship aspirations.
With Mike Conley injured and Donte DiVincenzo and Nickeil Alexander-Walker struggling at point guard against the nasty Rockets defense, coach Chris Finch turned to Dillingham, and Dillingham electrified the Wolves.
He had everything working, from knocking down floaters to finding Rudy Gobert for lob dunks. He rallied the Wolves from an 18-point deficit in the third quarter to take the lead late in the fourth quarter. He had 12 points, seven assists and was a plus-26 in 25 minutes.
And when he seemed poised to cap a triumphant night, he dribbled into the corner and was stripped by Amen Thompson, who went back the other way and tied the game with a layup. Dillingham sat for most of overtime, and the Wolves lost.
“I played solid, super solid, then coach had told me to push, I turn it over and we’re going to overtime,” Dillingham said. “Just little things like that, I could’ve been way better.”
That game stayed with Dillingham because it represented both what he could be at his best and the difficulties he had in acclimating to the NBA. His first step is electric, and he was one of the few Wolves players capable of creating his own shot.
However, his lack of size is something opponents hunt, and his free-wheeling style of play can leave him prone to turnovers that erode the trust his coaches need for him to play in big moments.
Unlike many top 10 draft picks who chafe when the minutes don’t come their way, Dillingham is fully aware of the things he needs to do better as his second season approaches. His rookie season was difficult. It tested him mentally in ways he did not anticipate. However, he also understood why Finch did not have him in the rotation for most of the season.
“I’ve worked hard, so obviously I want what’s best for myself,” Dillingham said. “But we were winning games, I’m in the Western Conference finals. So it’s like, how mad can I be? I should be happy for our team, where we’re at.”
Dillingham averaged 4.5 points and 10.5 minutes in 49 appearances last season, not what was expected when Wolves president of basketball operations Tim Connelly traded into the No. 8 pick in the 2024 NBA Draft to grab him.
As he prepares for his second season, Dillingham might be one of the most important players on the roster.
If he takes a significant step forward and becomes a rotation piece who can make plays for others and provide microwave scoring off the bench, it will be a massive boon to the Wolves’ chances to contend in the West. If he does not yet appear physically ready to contribute, they might have to think long and hard about looking for another guard to add.
At the time, the Wolves were desperately in need of depth behind Conley and looking for a point guard of the future. Connelly loved Dillingham’s creativity, shot generation and handle. Connelly believed Dillingham was in line for significant playing time in Year 1.
“I definitely thought I was going to play,” Dillingham said.
A few months later, the Wolves shocked everyone by trading Karl-Anthony Towns to New York for Julius Randle and DiVincenzo. Adding DiVincenzo essentially zapped all of the open minutes that could have gone to Dillingham. The tumult from the trade contributed to a slow start to the season for the team, which gave Finch little leeway to play a 19-year-old, undersized rookie at the game’s most complex position.
“He had a hard time last year not playing,” Wolves offensive coordinator Pablo Prigioni said. “All these young guys coming in from college have the expectations that they are going to have a lot of playing time. Sometimes things happen when you are on a team that is in a rebuild and not playing for anything.
“In our case, we were trying to fight for a championship, and sometimes those young guys don’t have the playing time they expect.
When he did get on the court, Dillingham was fighting a familiar internal battle, trying to play within the structure his coach wanted while also holding onto the ingenuity that makes him who he is.
The first word used to describe his style of play is “shifty.” Dillingham was never one of the tallest players growing up, so he worked hard to develop a lightning-quick handle and a knack for hitting off-kilter shots that allowed him to work around bigger bodies.
In many ways, he has a game developed for the social media era, hunting highlights with every crossover and slathering a little extra hot sauce on his jumpers and finishing package.
Rob Dillingham with a pair of crafty buckets 😯
He scored 27 points and dished out 9 assists in the @Timberwolves preseason victory tonight! pic.twitter.com/bXjQn5ebo0
— NBA (@NBA) October 14, 2025
The swag has made him a hit with the younger crowd. He has 1.1 million followers on Instagram. He has his own Nike PE shoe. When he checks into a game at Target Center, he already receives one of the loudest ovations from the crowd. His fans flock to him when they see him around town.
Dillingham also took a decidedly new-age path to the NBA. He started playing high school ball in Lincolnton, N.C., outside of Charlotte, then attended Kanye West’s Donda Academy for his junior season before leaving to play his senior season in the Overtime Elite league in Atlanta. He played one season at Kentucky before jumping to the league.
“I’m not super tall; I come from a regular town, so a lot of kids can relate to me,” he said. “People have seen my journey since I was a younger player, so they understand I really worked to get to where I am today.”
The constant change meant Dillingham had plenty of practice in earning the trust of new coaches. The flashy dribbling and kickouts on his jumper may be big hits with the kids on Instagram, but veteran coaches like John Calipari and Finch might view it a little differently. Both encouraged him to simplify his game, starting with the easy play and building from there.
“I’m gonna do what coach is saying, but I’m not a robot either,” he said. “You can’t lose what you have, but you also have to fit into where your team wins, and it can’t be about you.”
This is Dillingham’s second season in Minnesota, meaning he has been in one place — playing for one coach in one system — longer than anywhere else he has been since he was a sophomore in high school.
Finch is famous for giving players freedom. He likes to say he sets up left- and right-hand bumpers and gives the players the autonomy to operate within them. However, he does need discipline and decision-making from his point guard, first and foremost.
Finch started by pushing Dillingham to commit to the defensive end. Listed generously at 6 foot 2 and 175 pounds, he is the kind of player Kevin Durant was referring to this summer, who will be targeted over and over again in a league that is evolving out of the small-ball era.
“If you’re 6-foot, 6-1 and you’re not a bulldog like Davion Mitchell or Jrue Holiday on the defensive side, or on the offensive side if you’re not a flat-out savant like Kyrie (Irving), where you can score on dudes that are 7-feet easily in ISO, then I just can’t see it,” Durant said on the “Mind the Game” podcast this summer.
Finch has generally been measured in his comments about Dillingham since he joined the team, but one area in which the coach speaks glowingly about him is the effort he is putting forth on defense. Dillingham will wear a bull’s-eye on his back against most teams, but Finch has been pleased with the competitiveness and determination he has shown on that end.
“The non-negotiable is competing on defense, and I thought he did that last year,” Finch said. “That’s probably where I felt he had the best growth in his game, just his ability to go out there and fight, kind of learn and just navigate some tough circumstances at times.”
Perhaps unexpectedly, the offense has been, in some ways, the bigger adjustment for Dillingham. Finch wants him to focus on getting into the paint, putting pressure on the defense and finding his teammates for open shots.
Dillingham is an excellent passer, but the shift in mentality from scorer to facilitator is taking some time to take root.
“The playmaking is probably what we need from him more than anything else,” Finch said. “The scoring will come secondarily. And we need that change-of-pace guard. So if he leans into that and gets really good at those things that he can already do well, then he should be fine.”
The preseason has been underwhelming. In his first three preseason games against NBA teams, Dillingham is 8 of 28 with eight turnovers. He did have 18 assists in those games and finally flashed in a game against the Guangzhou Loong Lions. The Chinese team was entirely overmatched, but at least Dillingham dominated with 27 points and nine assists.
He was not taking any victory laps after the game, speaking with the same cautiousness that defined his rookie season. Dillingham did not grow resentful toward Finch for the lack of playing time. However, he struggled mentally to handle the first true adversity of his playing career.
“My mind completely goes straight to negative before it goes to positive because I’m always critiquing myself,” he said. “But I feel like that’s what I’m working towards now, just having a positive mindset and giving myself the benefit of the doubt.”
Dillingham was solid on Thursday night in Chicago, putting up 13 points and five assists with only one turnover, a nice step forward after what he called “an up-and-down” start to the preseason.
In last season’s loss to the Oklahoma City Thunder in the Western Conference finals, the Timberwolves badly needed another player who could handle the ball and be a threat to score on the perimeter. If Dillingham can become that guy this season, the Wolves will be in business.
After Nickeil Alexander-Walker left for the Atlanta Hawks, there are minutes to go around. Dillingham, Terrence Shannon Jr. and Jaylen Clark are all in the mix for that spot.
“It’s not about your raw numbers. Is Ant going to trust you? Is Julius (Randle) going to trust you?” Connelly said. “The reason we do trust them is because of their tremendous work ethic. They’re exactly the type of guys that we’re excited to have in our building. Self-motivated, tough, competitive, team-first guys.”
The coaches like what they have seen from Dillingham in practice, the way he plays within himself and operates more like a game manager than a gunslinger. He is not dribbling the air out of the ball as much and is pushing the pace to get one of the worst transition teams in the league out and running.
“He’s open-minded and trying to do the things that Finchy’s asking him to do,” Prigioni said. “Now he has to translate it in games.”
This is going to require patience from all involved.
Dillingham will need to give himself some grace as he finds his way and avoid dwelling on the struggles. Finch will need to let his young guard play through some mistakes so he can learn on the job and not worry too much about a loss here or there early in the season while they work to develop him. Fans will need to try to stay levelheaded from game to game, resisting the urge to call for his benching when he plays poorly and avoiding pronouncing him the starter when he plays well.
During the All-Star break last season, Dillingham posted a message on Instagram. “Stick w me,” read the caption above a motivational stanza. He’s been through this before, and he has come out on the other side of it every time. Now he has to do it again.
“‘I know it’s difficult, and you may think you can’t survive it,” it read. “But you’ve felt like this before, and you know exactly what happened because you did survive.”
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