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Kanye West Donda Debacle Divides a Kentucky Hoops Signee’s Family

When Robert Dillingham, a highly recruited point guard and a marquee player for Kanye West’s Donda Academy basketball team, signed a representation agreement with agency powerhouse WME last June, he was taking advantage of his newfound earning power now that name, image and likeness deals are permissible for high-school athletes.

By August, WME had helped Dillingham negotiate a “brand partnership” with Kinlo, Naomi Osaka’s skin-care product. At least two other endorsement deals followed.

There was just one problem. Robert was only 17 when he signed with WME, and nobody asked for his father’s permission. Now the contract may wind up disputed in court. Donald Dillingham, Robert’s father, says he wants to invalidate any contracts his son entered into as a minor. It is not clear whether the elder Dillingham can do that, but he said he has hired an attorney to explore his legal options.

Robert turns 18 in January, when he will become a legal adult for the purposes of such contracts, but Donald says his son should not have been allowed to enter these agreements without his OK.

Robert Dillingham’s marketability is an outgrowth of new NIL rules shaking the top levels of college and high-school sports. The smooth 6-foot-1 guard’s shooting and ball-handling skills have landed him the No. 8 spot in ESPN’s national player rankings. He attracted interest from every major college program—including Kentucky, with which he recently signed an NCAA letter of intent. He has a growing profile on Instagram, with nearly 300,000 followers, and when he signed with WME, he was still part of the massively hyped Donda Academy squad founded by Ye, as the entertainer now calls himself. One of Robert’s teammates at Donda, A.J. Johnson, also signed with WME.

Robert’s mother, Valaaulia “Lia” Tailele, co-signed the WME agreement, agreeing to take 5% of any NIL earnings her son makes, while the agency, with a market cap over $10 billion, would garner 15%. Sportico reviewed a partially executed copy of the agreement, which was not signed by a WME representative, as well as a guarantor agreement that acknowledges the client is a minor. The guarantor agreement was signed by Tailele and had a line for the father’s signature. It was left blank.

Not long after the ink dried, WME found itself in the middle of a family dispute. Donald Dillingham—who never married Tailele but was Robert’s custodial parent, according to a court-ordered child support document reviewed by Sportico—says he was never informed of the WME contract until after it was completed.

The WME snub is one of the many ways in which Dillingham says he has been cut out of his son’s life since Robert hastily left their rural North Carolina home for Southern California, and Donda, in October of 2021. In the elder Dillingham’s telling, Robert was lured away from his home and his prep school in Charlotte, Combine Academy, by people trying to capitalize on his son’s sudden potential as an endorser—among them a small-time North Carolina basketball promoter and one of the world’s most famous, and now infamous, entertainers.

Robert Dillingham’s journey, and his father’s frustrations, point to a confusing new era in youth sports, especially in basketball and football, where a glossy NIL industry that promises, and sometimes delivers, riches to talented teenage players is built atop an older, often seedy system of college player recruitment, where under-the-table payoffs, sketchy prep schools and academic fraud are common.

In the case of the Dillinghams, this new system has ripped apart what were already strained family connections.

“I just want people to know this story, to show what can happen if you’re a parent,” Donald Dillingham said. “The problem with NIL is these kids start thinking they’re grown and keep thinking they can make grown people’s decisions.”

Robert and Donald Dillingham, when Robert played for Combine Academy in North Carolina. Courtesy Donald Dillingham

Kanye West’s involvement in Robert’s budding career has created several decision points for the player—most recently with the sudden collapse of Donda in the wake of Ye’s repeated antisemitic statements. A representative for Ye did not respond to calls and messages from Sportico. As Donda’s team dissolved, Robert was forced in late October to make another move, this time to the Atlanta-based sports academy Overtime Elite.

Backed by Amazon money, OTE, as the academy is known, offers high-level teenage players the opportunity to earn money as professionals, or to attend and train as amateurs while maintaining their NCAA eligibility. Those players choosing the NCAA route can still make endorsement deals, and Sportico has learned WME assisted Robert in negotiating two NIL agreements with Brooklyn-based Overtime Sports, the digital media brand that is the parent company of Overtime Elite. When it comes to NIL deals, Overtime Sports and Overtime Elite stand as separate entities.

“We don’t comment on specifics but navigate each unique family dynamic by working directly with the player, and if they are under 18, we also include their parents or guardian,” Tim Nevius, OTE’s vice president for regulatory affairs and athlete advocacy, said in an email. “OTE does not offer NIL contracts, but players are free to sign endorsement deals with third parties, consistent with state law and NCAA rules, the same as many other high school players.”

None of these moves—the transfer to Donda, the WME contract, the Overtime switch or the Kentucky signing—happened with the consent of Donald Dillingham, a retired firefighter who has coached recreation league basketball for the last three decades in Hickory, N.C., and who claims he was often the primary caregiver for his son.

“I knew nothing,” said Dillingham, who also mentioned he has no idea who is handling Robert’s earnings, which may be substantial. During a brief conversation with Robert in early November, his son told him he was offered $250,000 for endorsing Overtime Sports.

WME declined to comment on Robert Dillingham, citing “client confidentiality.” Tailele, Robert’s mother, did not return text and voicemail messages. Through an OTE spokesperson, Robert declined an interview request.

The elder Dillingham said his son was convinced to leave his home in Hickory, and Combine Academy, by Rico Grier, a basketball promoter who was sentenced to three years on federal drug conspiracy charges in 2013.

Dillingham accuses Grier, whose LinkedIn account describes him as “Head of Talent Management” at Beymoss Sports LLC, of working in concert with Adidas. Robert’s departure from North Carolina to California took place not long after Combine Academy switched apparel sponsors from Adidas to New Balance. Combine Academy president Jonah Baize declined an interview request.

Shortly after joining Donda, Robert verbally committed to North Carolina State, an Adidas-sponsored school. He rescinded that commitment several months later and pledged to attend Kentucky, a Nike school.

At Donda, Dillingham and other players played in Yeezy sneakers, designed by Ye’s company and manufactured by Adidas. An Adidas spokesperson responded to an interview request and questions about Robert Dillingham with an email saying: “We won’t comment on unfounded rumors. And to be clear, Adidas has never had a partnership with the Donda Academy basketball team.”

When contacted by phone last week, Grier said he could not talk but would be available the next day. He hasn’t responded to calls or text messages from Sportico since.

Grier, Dillingham said, heightened tensions between him and Robert’s mother to get closer to his son. He said Grier wooed his son with gifts, including an $1,100 phone; pushed him to transfer to Donda; and cut Robert off from contact with Donald and Robin Dillingham, Robert’s aunt, who, according to Donald, helped raise him along with Donald in Hickory.

Cam Carter runs a marketing and PR agency in Charlotte and worked briefly with Grier. He said Grier approached other touted teenage basketball stars in the area, but most of those efforts failed.

Robin Raimey—whose son, Aden Holloway, is another nationally recruited point guard prospect from North Carolina—said Grier tried to get close to her son, setting up a recruiting Zoom call for Holloway with Winthrop University, a small D-I school. “I love Winthrop, but Aden was never going to Winthrop,” Raimey said. Holloway has signed a letter of intent with Auburn, turning down offers from Michigan and Tennessee, among other schools.

“He said to me once, ‘I see myself as a manager for these kids,’” Raimey said. But when she began seeing “the dysfunction and the problems” Grier was creating between the Dillinghams, Raimey cut off contact with Grier. “I don’t want to be around people like that,” she said.

Carter said Grier was more successful with Robert, “trying to take him under his wing and trying to, quote, unquote, manage him.”

In the early fall of 2021, Robert boarded a plane en route to Simi Valley, Calif., to visit the Donda team, without his father’s knowledge. In early October, a few days after his return from the visit, “Kanye gave Robert a call, and he was in California in 48 hours,” Carter said.

“All these kids (who went to Donda) were sold on the idea that they’ll be the first Yeezy athlete,” he added.

Dillingham heard nothing from Robert for weeks after the move to California, and posted on Facebook wondering about his son’s whereabouts.

Father and son began having sporadic communication thereafter, but Dillingham said he doesn’t know who was supporting his son or who negotiated contracts on his behalf. He said that in October, Robert told him he would earn $10,000 for appearing in a Kinlo advertisement with Osaka, but that he didn’t yet have a bank account.

He also said he never knew if his son took any classes while at Donda—which was never accredited.

Kinlo promotional photo with Robert Dillingham, Naomi Osaka and other athletes
Robert Dillingham (left) was featured in promotional material for Naomi Osaka's Kinlo skin-care products. KINLO

The entire saga exacerbated divisions within the Dillingham family. Donald was beset by back problems that forced him to retire from his job at a local fire department in 2009, and he said his back issues and diabetes forced him to go on disability assistance in 2017. Meanwhile, Robert’s mother was often exhausted from her full-time job at a local factory, according to Donald and Robin Dillingham, leaving them to do much of the work of raising Robert.

Dillingham said Tailele, who grew up in Samoa, “doesn’t know anything about basketball, or recruiting,” but says he always tried to include her in any major decisions for their son. Still, the two often had an acrimonious relationship, he said, which wasn’t helped when Dillingham went to court to have Robert’s mother pay child support in 2017. Court documents from that proceeding identify Donald as Robert’s custodial parent, and Robert as living with Donald.

Dillingham said Grier came into the picture just as Robert was becoming known for his on-court prowess. He said he was initially cordial with Grier, but later told him to stay away from his son, which led to arguments. During one heated encounter, Donald says Grier told him that Robert should “emancipate” himself from his father.

A few months later, Robert was gone to California.

Dillingham said early this year he explored taking legal action to assert parental rights; he decided against it after being advised that the issue would be moot when Robert turns 18 early next year. But Dillingham says he changed his mind when the mother of a former NBA player reached out to him in November and told him to push the issue. He has since retained attorney Jordan Moir of the King law firm in Morganton, N.C. Moir did not respond to requests for comment.

Under North Carolina law, children under the age of 18 are generally classified as under the “supervision and control” of a parent and thus lack the legal capacity to enter into binding contracts. However, North Carolina law crafts exceptions for certain types of transactions, including when a child has been declared “emancipated” by court order or when an non-emancipated child signs “a contract pursuant to which a person is employed or agrees to render services as a participant or player in a sport.” In that latter scenario, a court can approve the contract after a review of the best interests of the minor and other factors.

In the case of the WME contract and the NIL deals, it appears the companies involved considered Lia Tailele’s approval to be sufficient.

Dillingham went to visit OTE in mid-November, and he and Robert had a brief conversation. “Robert was mad because they had him on restriction from playing, because they said he had COVID,” he said, his voice rising. “He had COVID, and I didn’t know about it.”

The conversation ended abruptly after Dillingham told Robert he was there to tour the Overtime campus, which upset Robert. He said his son left the room muttering about his father under his breath.

While the OTE staff was polite and showed him around the multimillion-dollar facilities, Dillingham said they didn’t give him much of an answer when he asked why they never contacted him about Robert’s enrollment there, or when he requested that they keep Grier away from his son. “They said, ‘We don’t get into family business,’” Dillingham said.

The past year has been “crazy,” Dillingham said, and depressing. “My father wasn’t there for me, and so I made it a point that I was always around for Robert.”

Though he acknowledges it’s probably no longer possible, he added, “All I’ve ever wanted from the beginning is to have my son come home.”

Additional reporting by Eric Jackson, Michael McCann and Teri Thompson.

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