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Robert Dillingham: From Kanye to Kentucky

Last Updated: September 26, 2022
As the first major recruit to come out of Kanye’s Donda Academy hear how Robert Dillingham plans to succeed on and off the court as his hoops journey heads to Lexington.

Basketball has taken Robert Dillingham all over during the last couple of years.

The No. 5 men’s basketball recruit in the nation for the class of 2023 according to ESPN, went from Combine Academy in Lincolnton, North Carolina to Kanye West’s Donda Academy in Simi Valley, California. He played for Chris Paul’s Teacm CP3 on the EYBL circuit, covering the country this summer. Next year he’s heading south to join the University of Kentucky Wildcats.

The Wildcats pulling in a top-five prospect is nothing new; John Calipari has made a habit out of assembling top recruiting classes. Dillingham isn’t exactly unique in this new era of college sports, either. Like a whole host of Wildcats before him, including TyTy Washington and Oscar Tshiebwe, Dillingham should have dozens of opportunities coming up to capitalize on his name, image, and likeness.

Still, there may not be anyone more qualified to be the poster child for the wide world of NIL in 2023 than Dillingham.

Speaking to Boardroom as he officially announced that he’s signed with WME for representation on NIL deals, he talked about what he hopes to accomplish in the space and how his time at Donda Academy prepared him for the next level.

“Once I came out here, I felt like it was just easier for me to focus,” he said. “I was away from home and it was just like, I became more of a pro out here.”

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The Donda Way

Dillingham is notably the first major recruit to emerge from Donda Academy, so in many ways, his play in college will be what puts a Ye-branded education on the map.

He’s been in that situation before; as one of the first basketball players to commit to Donda, Dillingham needed to turn around and play the role of recruiter himself. He educated top prospects from around the country about the program and gave his best pitch to get them to come and share the court with him.

It was an easy sell. Aside from one of the most recognizable names in the world being attached to it, Dillingham says Donda Academy’s flexible structure allowed him to hone his game while also completing his academic requirements. Basketball could truly be his main focus as long as he finished his schoolwork on his own time.

“It’s easier to finish your work,” Dillingham said of Donda. “I always finish my work ahead [of time] and then I have more time on my hands to do whatever I want; mostly be in the gym.”

But make no mistake: barring injury, Dillingham is going to play basketball professionally. That will be his job.

(And these days, no one prepares future stars for the pro game quite like Kentucky’s Coach Cal.)

Donda’s schedule also made it easier for Dillingham to balance his dual commitment to athletics and academics. He was able to take classes throughout the calendar year such that during basketball season, his course load was relatively lighter.

Perhaps just as importantly, Dillingham says, Donda Academy let him see firsthand what it takes to succeed in the business world from one of the biggest innovators across multiple industries: Ye himself.

“He puts us in a position to see it,” Dillingham said. “That’s part of the reason I went there, because it’s a lot of everything, and you learn how to become a businessman also you’re playing basketball.”

The Wildcat Way

When he gets to Lexington, Robert Dillingham will be expected to act like a pro. He joins generations of hoopers who have built Kentucky’s legacy as a direct pipeline to the NBA. In fact, Calipari was the first to open the doors to his practices to NBA scouts by holding a now-annual pro day back in 2014.

So, what will Dillingham bring to the Wildcats?

He has a full bag to pull from. A perhaps undersized guard (his listed height is 6-foot-2) who combines flash and poise with an ability to score at the rim, from mid-range, or from deep, he also prides himself on being able to find the open teammate when he doesn’t have a shot himself. Or, as he puts it:

“Just an all-around player. A playmaker. A player who wants to win.”

That should go over just fine for a Wildcat fanbase that is hungry after a disappointing first-round NCAA Tournament exit in 2022 and a losing season in 2021.

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Dillingham is the current crown jewel of Kentucky’s 2023 class (so far, No. 1 overall recruit DJ Wagner hasn’t committed yet). As it stands, he is poised to get the most attention at the school with the largest and most crazed college basketball fanbase in the country.

With one year of NIL under our belts, we’ve seen what that means. Washington made the most of it in his one year at Kentucky with Porsches, crypto, and caviar. It would be foolish to think Dillingham hasn’t considered it as well.

“You take advantage of everything you can do, not just take advantage by doing stuff to make money,” Dillingham said of the fast-growing NIL landscape. “To build your brand as a person and a player so when you get to the next level, brands want to mess with you.”

And that’s where Robert Dillingham sees himself in just a couple of years. Like any top-10 recruit, the NBA is more than just a pipe dream; he knows Adam Silver is going to call his name on draft night. And as intimidating as that might be for a 17-year-old to think about, he is utterly unfazed.

“I’m never nervous to play against anyone,” he said. “I just feel like I’ve been playing too long to not be able to play basketball. Ja Morant came in and hooped off confidence, so I feel like I can be a player like that soon.”

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About The Author
Russell Steinberg
Russell Steinberg
Russell Steinberg is an editor and writer at Boardroom. He came to the brand in 2021 with a decade of experience in sports journalism, primarily covering college basketball at SB Nation as a writer, reporter, and blog manager. In a previous life, he worked as a social media strategist and copywriter, handling accounts ranging from sports retail to luxury hotels and financial technology. Though he has mastered the subtweet, he kindly requests you @ him next time.