'The experience boosted me': Inside Rob Dillingham's strange journey to the NBA

NEW YORK -- ON THE 28TH FLOOR of a five-star hotel in midtown Manhattan, Rob Dillingham sat at a table near a window that overlooked Madison Avenue, which for years has turned athletes into pitchmen. It was the day before the 2024 NBA draft.

He smiled, nervously.

He leaned forward and tapped his leg.

Dillingham, 19, who spent his lone college season at Kentucky, went to three high schools, all conveyor belts for basketball players, in four years. He moved cross country to attend his second high school, Donda Academy, which was founded by Ye, the rapper formerly known as Kanye West. Donda closed at the start of his senior season because of the fallout from Ye's antisemitic comments.

"I would say the experience boosted me because ... it gives you a little bit of adversity," Dillingham said of his path.

His voice trembled as he spoke.

"People that don't go through adversity, that touch adversity and their first time touching it is later, it's harder to handle," he said. "I would say it just built me to be more mentally strong way quicker, and it gave me confidence to be me earlier."

Before Donda, Dillingham started at a training academy turned prep school 20 minutes from his North Carolina hometown. And after Donda, he finished at Overtime Elite, a league for basketball players in Atlanta. In between, he was a basketball influencer and SLAM Magazine cover star.

Dillingham, the young man, navigated the intersection of celebrity, exposure and opportunity. Dillingham, the basketball player, has a different challenge: earning minutes in the NBA. On draft night in Brooklyn, New York, he was taken eighth overall by the San Antonio Spurs, who immediately traded him to the Minnesota Timberwolves, last season's Western Conference runner-up.

Dillingham's journey is a lens through which to examine modern-day American youth basketball, which increasingly eschews incremental development for brand growth. It was a means to his draft night end. But as a pro, Dillingham realized he had to start from the beginning, despite being a product of a system that purported to help him avoid just that.

Before he got to July's Las Vegas summer league, Dillingham called Mike Conley, Minnesota's starting point guard who was heading into his 18th year.

"I have a question," Dillingham asked Conley, "about pick-and-roll defense."

IN MAY 2019, months before Dillingham started high school, former NBA commissioner David Stern arrived at a happy hour in Brooklyn. He was there for a showcase of the top high school boys' and girls' hoop players in the country hosted by Overtime, which offered basketball content through high-production video and social media. Before he passed away in January 2020, Stern was one of Overtime's early investors. He held court about the prospect-to-pro pipeline.

"And the parents [of the prospects] were there complaining about the existing ecosystem," said Farzeen Ghorashy, then-Overtime's chief strategy and financial officer and now its president.

It was clear there was a problem.

By September, Overtime hired the manager of player programs and team services from the Philadelphia 76ers, Le'Sheala Dawson, and asked her to talk to parents of basketball prospects and synthesize their concerns. She spoke to 75 sets of parents during the pandemic.

"And she came back with this master spreadsheet," Ghorashy said. "And it was a very consistent theme of things, right?"

Parents vented about spending time and money -- "they could have bought a house with the money they had invested," Dawson remembered being told -- but not getting results. Prospects worked with individual trainers and were on high school teams that, in some cases, played national schedules. And they competed in AAU, one of the United States' main vessels for young players. Dawson kept hearing the same refrain: The players were supposed to be getting better at skills that would set them up for specific roles in the pro game, but it wasn't happening.

"And so we said to ourselves, 'Why don't we just reverse engineer something for them that works?'" Ghorashy said.

Overtime Elite was born in 2021 and had the tenets of a basketball academy (the players lived near and trained at NBA-level facilities), where they could enter at 16 and stay until they left for college or the pros. But it was also an actual basketball league, and groups of scouts would visit on a regular basis. There's also an Overtime YouTube page that now has more than 3.5 million subscribers, giving the kids a worldwide audience.

"The notion of paying an athlete, putting professional resources around them at a very young age is not something that you really see in high school basketball or football," Ghorashy said. "But you cross a body of water into Europe, and Luka Doncic and all these players are getting that sort of environment since a really young age.

"You look at all the sports, especially soccer. That's basically the model that is being replicated."

That model had fans among the game's best teachers. At a conference in 2017, legendary Connecticut women's basketball coach Geno Auriemma talked about winning -- the attitude it required and the sacrifice it demanded. Auriemma's anecdote about his time coaching his son's AAU team went viral. In the U.S., he said, there are six games and one practice per week. The schedule is the opposite in Europe, where players honed their craft.

But in the U.S., there are handlers, managers and sneaker representatives.

"People [in the U.S.] have other incentives," Ghorashy said. "It's a lot cleaner abroad because the people around [the players] aren't so focused on the intermediary steps. They know they want to get to the NBA, and it's all about development."

STOP NO. 1: HOMETOWN

"WE PRIDE OURSELVES on resembling the European academy model," said Jonah Baize, one of Combine Academy's co-founders, along with eight-year NBA veteran Trevor Booker. Dillingham played there during his freshman and sophomore years in high school.

In Dillingham's case, his older brother, Denzel, saw a future for him as a Division I prospect and knew that he needed exposure. Dillingham landed in Nike's Elite Youth Basketball League (EYBL) in middle school.

"But we knew that prep schools were becoming a thing," Denzel said.

From his time playing AAU basketball, Dillingham's brother had a relationship with Jeff McInnis -- a former North Carolina Tar Heel and 11-year NBA veteran -- who was the coach at Combine in Lincolnton, North Carolina, a city of about 11,000, 20 miles from Dillingham's hometown of Hickory and 40 miles northwest of Charlotte.

"I didn't really want to stay in my hometown," Dillingham said. "Even if you do super well, it's not like you'll get a bunch of recognition because you haven't really played a lot of people. So, it's like, why not go to the school where you can play against better players?"

Combine started as a training facility in 2012 before transitioning into an accredited school the following year. During Dillingham's time there, he blossomed into five-star recruit. Several high major schools were after him. He had a support system at Combine. His brother, a mentor and basketball tutor, helped the school with player development. And his sister, Pai Tailele, worked in the school's executive office. But Dillingham outgrew it.

Baize said that Dillingham came to the school's leadership and explained he had an opportunity to leave Combine and transfer to Donda Academy, leaving the North Carolina countryside for Southern California. As former basketball players, Baize and Booker supported Dillingham. They knew he was grounded and appreciated Combine's role in his development. Dillingham could thrive on the change and the challenges -- of moving cross-country, of standing out amid a sea of brand names, of setting himself up for future success when none is guaranteed -- that would make him stronger.

But for some kids Dillingham's age, it could be what damages them permanently.

"I feel for the parents just because there're so many people pulling at the top players," Booker said. "And it's hard to know who to trust out here. So that's why you see a lot of these kids changing schools. They're being promised something.

"And then they get to the school, and it doesn't become fulfilled."

DONALD DILLINGHAM WROTE a 369-word Facebook post in October 2021.

"As Rob's dad, I was not informed about the offer to attend Donda Academy," he wrote the same month his son transferred.

"Neither Rob's mother, brother or sister have communicated Rob's whereabouts to me. I have not seen or talked to him for 3 weeks. I have seen the trio in North Carolina, so I know that Robert is alone in Los Angeles, California."

In the post, Dillingham's father claimed Ye "contacted" his son and asked him to decide immediately about attending Donda.

"Of course Rob with his sixteen-year-old mind, would say 'yes,'" the father wrote. According to Dillingham, the decision to go to Donda was approved by his mother, Valaaulia "Lia" Tailele. Shayla Scott, who was the chief operating officer of Donda Sports, said that she wasn't privy to how players' families arrived at their decisions. When asked about his father's influence on the decision, Dillingham responded: "No influence." When asked before the draft to characterize the father-son relationship, he said: "Kind of good."

Dillingham's father also claimed the school was unaccredited and that Dillingham was traveling "with a known convicted felon who has created a wedge between my son and myself, which has given the felon the opportunity to influence and manipulate Rob and his family with the promise of money."

In a December 2022 story from Sportico, Dillingham's father named his son's alleged influence and identified him as "a basketball promoter who was sentenced to three years on federal drug conspiracy charges in 2013." Dillingham's parents declined interviews with ESPN, and the man identified in the Sportico story could not be reached for comment.

"It's just a miscommunication," Dillingham's brother Denzel, said of the family disagreement. "And I think that, when somebody takes a risk, of course people are going to feel hesitant, but it's with the best interest of that individual at heart. I think it comes from a concerned and caring place, more so than just trying to do anything to potentially harm that person."

That risk came after the 2020-21 school year at Combine. Dillingham got a call from Dorell Wright, a 2006 NBA champion with the Miami Heat, who recruited -- before later becoming coach -- for the prospective Donda high school.

"Kanye's team got on the call," Wright told ESPN. "They said they wanted to do a school. I recruited kids and just let them know what the potential of the program could be -- not only for their basketball careers, but off the court as well. And Rob already was a well-known name, so it wasn't too hard for him to get that notoriety off the court."

Dillingham and his brother flew to California to meet Wright, who laid out his pitch in person. There was the pull of Ye, one of the most famous people in the world, and his teammates, some of the highest ranked players in the country. They met for 45 minutes with Ye. "A surreal feeling," Dillingham's brother said.

Ye watched players work out and described his vision for Donda, named after his late mother, a former English professor. Located about 50 miles northwest of Los Angeles, Donda's high school students wouldn't have a traditional school building like the ones where the prekindergarten through eighth graders attended. There would be online classes, and the basketball team would be set off on its own. Players would live with their teammates. They would be fed by Ye's chef. They would be known as the Doves.

Dillingham was all in -- even though the Doves technically didn't yet exist and Ye was a controversial figure. Among other incidents, Ye said on TMZ in 2018 that 400 years of slavery "sounds like a choice." He later apologized but the damage was done.

But Ye still had considerable influence.

After his sophomore year at Combine, Dillingham began playing AAU for Team CP3, fronted by future Hall-of-Fame point guard Chris Paul. His game, slick and stylish, was perfectly tailored for viral social media clips. He developed a following, leading to fans packing gyms and staking out hotels on the AAU circuit.

"I went from being kind of known to being really known," Dillingham said of what happened leading up to his transfer. "And it was like you're playing basketball; you're doing everything you love. Why not build your brand?"

STOP NO. 2: HOLLYWOOD

AT THE DSTRKT, a basketball complex about 30 miles northwest of downtown L.A., Ye blasted Donda, his album that had been released weeks prior. It was the fall of 2021, and Dillingham and his new teammates were at a team photo shoot, which more closely resembled a release party in the Hollywood Hills.

The players, who would be empowered to wear designer clothes on road trips instead of matching sweats, tried on eccentric gloves and face coverings, hamming for the camera.

"That s---," Scott said, "was a whole concert."

By January 2022, Dillingham and 10 teammates, including sought-after recruits Jalen Hooks, Zion Cruz, Javonte "JJ" Taylor and Jahki Howard, appeared on the cover of SLAM. Ye, in a black hoodie and sunglasses, was in the center of them all.

Dillingham moved to L.A. hoping to cash in on his name, image and likeness, payments for which were allowed in California -- but not North Carolina -- for high school players at the time.

He went from an all-boys school in North Carolina to dinner with Ye and an apartment in L.A. The players lived near The DSTRKT, where the Doves played and practiced in their first season.

"Every game you came to was sold out. Every game you came to was on Instagram or YouTube," Dillingham said. "We had every rapper at our games, and you're playing basketball. [And the Instagram edits] are way [better] than everybody's edits just because it's Donda Academy."

As Dillingham darted around defenders in his Donda jersey, he sported Ye's Yeezy 500s, previously worn for style rather than basketball, on his feet. As Dillingham's popularity grew on social media, so did the number of Yeezy 500s on youth basketball courts.

Eight months into his time at Donda, in June 2022, a 17-year-old Dillingham signed a representation contract with talent agency WME, according to Sportico. Dillingham then landed a partnership with KINLÒ, a skin care brand from tennis superstar Naomi Osaka, in August 2022. Sportico said that Dillingham's father wanted "to invalidate any contracts his son entered into as a minor." According to Sportico, which reviewed documents, Dillingham's mother cosigned the WME agreement and signed a guarantor agreement, recognizing her son was under 18. Dillingham's father did not sign.

Dillingham told ESPN that he didn't end up receiving any NIL money at Donda. "But then the stuff happened with my dad, so everyone thought I was getting paid," he said. "And so there was no reason to start NIL and actually get paid if everyone is already portraying this image. I didn't really want that."

But questions mounted as Donda's second basketball season approached. A September 2022 story in Rolling Stone asked: "What the hell is going on at Kanye West's mysterious new private school?" The magazine also reported that nondisclosure agreements were signed at Donda. That added to the conjecture: What were they teaching the students? Where was the building?

Scott, a former high school athletic director, sent her two children to Donda's lower school. She told ESPN that Donda was accredited as a high school through K12 Private Academy in Virginia, which Donda paid for use of its curriculum. A representative for K12 Private Academy confirmed there was a partnership for the 2021-2022 school year.

Amid increasing media interest, Scott said the lower school's building moved locations in L.A.'s northwest suburbs. Security increased, too. "And because people don't have the access to Ye that they wanted, it was, 'OK, we're going to make up our own narratives,'" Scott said. At that point in September 2022, Scott confirmed there were non-disclosure agreements presented to families of the lower school's children. The Doves also had moved from The DSTRKT to The Sports Academy in Thousand Oaks.

Then, in early October 2022, Ye was photographed in a White Lives Matter shirt. Shortly after, he made several antisemitic comments in interviews and on social media, saying in one post on what was then Twitter that he would go "death con 3 on JEWISH PEOPLE." He was suspended from Twitter and Instagram. Adidas severed its partnership, and several athletes left his sports agency.

Donda closed in late October 2022, which ESPN reported was Ye's decision. Dillingham and the basketball team remained, but opposing teams began dropping the Doves from their schedules -- and the season was eventually cancelled.

"It was definitely a disappointment," Dillingham said. "It was frustration, because obviously you didn't really want to leave."

Dillingham suddenly had nowhere to play his senior season.

Scott said she cried.

STOP NO.3: WELCOME TO ATLANTA

"COACH CAL WANTED me to go to Overtime," Dillingham said.

When Dillingham was in 10th grade, then-Kentucky coach John Calipari visited North Carolina to recruit him and developed a relationship with Dillingham's mother, who liked that Calipari said her son would have to earn his standing in Lexington. Dillingham chose NC State over Kentucky in December 2021 but decommitted three months later, signing with Calipari and the Wildcats three months after that.

Days after Donda's season was halted, Dillingham transferred to Overtime Elite. In May 2021, months ahead of OTE's launch, Calipari pitted himself against the startup, where players could receive a salary and benefits. "We are not just competing against other colleges; we are competing against that too," Calipari told reporters at the time.

Five-star twins Amen and Ausar Thompson, who Kentucky had pursued, chose OTE instead in 2021. They skipped their senior year of high school, finished at OTE and prepared to go from there to the NBA, where they would be chosen fourth and fifth, respectively, in the 2023 draft. In 2022, OTE started offering a scholarship option, which allowed players like Dillingham to maintain college eligibility. Calipari eventually came around on OTE. He toured its NBA-level facilities and realized that OTE's players would be prepared for elements of big-time college basketball at Kentucky.

Dillingham's route there showed how players often are guided in different directions; a path Calipari would not go down at one moment was one he recommended the next. "I was going to go to school early," Dillingham said. "It wasn't really my decision. [Coach Calipari wanted me] to develop, get bigger for sure."

Starting when he arrived at Kentucky, Dillingham said that he and his father "have a great relationship again." Under Calipari at Kentucky, Dillingham played in just one NCAA tournament game. It took place in Pittsburgh, to where Scott -- a former Pitt women's basketball player -- had moved after Donda shut down. She and her family attended, and Dillingham hugged her kids before it. She cherished the moment.

"What that year and a half-ish meant for me personally and, hopefully, the impression that it made on Rob," Scott said, "Rob is just impressionable ... in everything that he does. And I know that because of the way that my kids love Rob still."

In his last college game, Dillingham's Wildcats were beaten by 14th-seeded Oakland University. Jack Gohlke made 10 3-pointers, falling one short of a record.

Gohlke, a sixth-year graduate transfer, previously spent five seasons in Division II.

THREE WEEKS BEFORE the Timberwolves opened the regular season against the Los Angeles Lakers, Dillingham got into a defensive stance. He bended his arm as if bodying up to an opponent. His knees were bent, too, and he arched forward.

While doing so, Dillingham wasn't on the hardwood at The Target Center. Instead, he sat in a room off the Timberwolves' practice courts. He relayed what he learned from Conley in July.

"He was saying put my forearm into him and get into the ball," he said. "Don't really push him."

Dillingham eased back into the office chair.

"And then as he's coming off the screen, step around with my right leg instead of chasing," he continued.

At 6-foot-3 and 6-foot-1, respectively, Dillingham and Conley are small guards in a league of giants. Dillingham wanted to know how to survive. Though Conley had watched Dillingham from afar, starting on Instagram and then at Kentucky, he wasn't sure what to expect once he picked up that call over the summer.

"He said, 'Man, I need to know, what's your thought on triangular screens?'" Conley said of Dillingham's question. He smiled. "I said, 'We're going to be alright,'" Conley said, impressed with Dillingham.

But Conley's expectation for young players had been altered in recent seasons. He said that he had been around at least one player who came into the league and didn't know what a backdoor play was, players whose one-on-one talent usurped their ability to play within the team concept.

"There are a lot of things, not just with Rob, but just anybody that age," Conley said. "They come in and they'll ask you a question about something, and I'll go, 'Don't you know that? You should probably know that one. Because I knew that at 12 or 10. We ran lines if we didn't pass it two times before we shot it. Those little things were etched in our mind.

"I think the younger generation has a lot more attention, but a lot more distraction as well to where they're more worried about a lot of other things."

But there's another way to look at it, too: Dillingham entered the league prepared for the hardest part of NBA life, which is a blur of hellos and goodbyes. For some players, where they live and with whom -- and for whom -- they play can change annually. "The league is helter-skelter," Conley said. Dillingham got a taste of that life at an early age.

When asked how prepared Dillingham is to help right away, Timberwolves president of basketball operations Tim Connelly was noncommittal. But Connelly did describe his team's conundrum: Dillingham was drafted because he filled a need; Minnesota was in search of a dynamic perimeter player, other than star Anthony Edwards, who can get his own shot whenever he wants.

At media day Sept. 30, head coach Chris Finch said he had already noticed Dillingham's development, a process that used to culminate before a player donned an NBA jersey. "We'll try to help [young players] get better wherever we can," Finch said, "and we'll put you on the floor with lineups that can help protect you where you're weak and extenuate where you're strong."

Dillingham knew he could score against anyone since he was a kid. And that hasn't changed. "I definitely see someone who is confident," teammate Nickeil Alexander-Walker said.

On defense, it wasn't that he didn't know how to guard a pick-and-roll. He needed to learn how to do it against players with NBA size and speed.

"We're hopeful that as he gets more and more comfortable in the NBA, he can make an impact sooner rather than later," Connelly said.

STOP NO. 4: THE LEAGUE

ON OPENING NIGHT in Los Angeles on Oct. 22, Dillingham did not play.

He didn't play against the Sacramento Kings two nights later, either.

Or in home games against Toronto, Dallas and Denver.

Then, on Nov. 2, Dillingham recorded two assists in a loss to the Spurs. Two days later, he scored his first career points in a win over the Charlotte Hornets. He had his best game four days later, scoring seven points in a win over the Portland Trail Blazers. He has played exclusively after the games have been decided.

Inconsistent playing time was expected, and its explanations make sense: lottery picks normally land on bad teams which have no other choice but to play them; Dillingham is on a championship hopeful. He's a conscientious kid, who worked hard at all his stops. He'll do the same in Minnesota, where he just needs time. After all, not many 19-year-olds would call their mentor before that mentor could call them, not many would care about mastering minutiae.

But when considering Dillingham's future, it's hard not to fixate on his past, on how the United States raises its basketball children. It's hard not think about the past six NBA MVPs, none of whom are American born. It's hard not to think about the past two No. 1 overall picks, both from France.

There was no amount of time on an AAU circuit or at a prep academy or in any development model, no matter the country, which could truly land Dillingham in Minnesota's rotation right away. But perhaps there is a better way than the maze of AAU tournaments, sneaker alliances and content creation opportunities that define American youth basketball.

The hope is that by the time the Timberwolves -- who qualified for their first Western Conference finals in two decades last season -- are ready for another deep playoff run, Dillingham is, too -- the 82-game schedule, in Dillingham's case, doubling as development.

Does Dillingham view it the same way?

"Yeah, for sure," he said.

Then, he paused.

"But at the same time, I feel like I can perform and do whatever I can to help the team," he said. "And I want to help right away."