Drue Moore had spent the last decade of his life preparing to shield his assets upon his death.
On July 21, 2016, the lawyer who co-founded Winthrop Intelligence, the successful college sports SaaS company, signed his last will and testament, naming his wife Kelly the executor of his estate and trustee of his trust.
Ben Moore, Drue’s cousin and fellow co-founder of Winthrop Intelligence, was appointed as a successor executor and trustee—a natural choice. The cousins, lifelong friends, had worked hand-in-hand to build their company and develop its flagship product, WIN AD, a comprehensive financial database tailored for university athletic departments.
By 2016, the business was thriving, generating seven-figure annual profits and providing its owners with what appeared to be a steady stream of passive income for the long run. But instead of settling into their success, the Moores pursued riskier ventures to further diversify their income, all while taking measures to shield their wealth from creditors, tax authorities and, as it played out, one ex-spouse.
This tumultuous era saw a series of legal actions undertaken by the Moore cousins and Winthrop, much of which raised questions of collusion. Even after Drue Moore’s death, the saga endures, with his death by suicide earlier this year igniting fresh questions, allegations, and yet another lawsuit over who is entitled to the spoils of Winthrop’s success.
As previously reported by Sportico, the Moores’ strategic shift aligned with their association with Robert Scott Brooks, who was previously imprisoned for falsifying loan applications and has been admonished by judges and attorneys in a number of other cases for his questionable legal tactics. Brooks quickly secured key roles within the cousins’ operations, including serving as the chief investment and financial officer at Winthrop Intelligence, their cash cow. Simultaneously, they enlisted Wyoming-based tax attorney Dennis Scott Robinson to help them create an elaborate lattice of trusts and LLCs aimed at asset protection.
Winthrop Intelligence, initially incorporated in Delaware in 2009, changed its domicile to Wyoming in 2017, a state known for its advantages in corporate anonymity. The company was registered through one of Robinson’s firms, Opes Registered Agent Services; another of his companies, Opes Directed Fiduciary Services, was designated as trustee for the cousins’ trusts. Winthrop continued to file its annual reports in North Carolina, where Drue Moore lived, listing his Durham, N.C., home as the company’s official address. However, Robinson’s name replaced Moore’s as Winthrop’s “managing member.”
The cousins’ operational roles at Winthrop in recent years remain unclear. However, contracts obtained by Sportico reveal that Drue Moore was still listed as the signatory for Winthrop’s WIN AD software agreements with schools, just weeks before he was found dead at his home on Jan. 10. He was 55 years old.
He died approximately six months after Ben Moore was incarcerated for contempt of court related to his divorce proceedings with his ex-wife, to whom he owes millions of dollars.
Drue Moore’s widow, Kelly, and their two children are now suing Brooks and Robinson, claiming their unfounded accusations of him embezzling Winthrop funds led to Drue’s death by suicide. Robinson vehemently denied the allegations in a statement, while Brooks did not respond to an email seeking comment.
In an amended complaint filed this month in North Carolina state court, Kelly describes her late husband as the unwitting victim of the lawyer and business partner he had entrusted. Kelly’s portrayal contradicts other characterizations of Drue, including those made in prior legal proceedings, which depicted him as the architect of schemes to conceal assets and manipulate the legal system. An attorney for the plaintiffs declined to comment.
This latest lawsuit describes Drue Moore’s final months as a frantic, anxiety-ridden struggle to appease the defendants. After being accused of improperly taking distributions from Winthrop, the lawsuit claims, Drue was “unduly pressured” into resolving the matter by transferring well over $1 million to Brooks or entities under his control.
To do so, the lawsuit claims, Drue liquidated his personal brokerage account, withdrew funds from educational and E-Trade accounts he had set up for his nieces, and cashed out of a “charity investment property” in Nairobi, Kenya. In addition to the money, the lawsuit says that he sent Brooks multiple high-priced watches.
Despite all this, Kelly Moore claims that on Jan. 3, Brooks sent Drue Moore a letter purportedly terminating his involvement with Winthrop and its affiliated entities. The letter demanded a full accounting of his personal assets and threatened criminal charges and public humiliation if Drue did not comply by Jan. 10—the day he died by suicide. The lawsuit further alleges that since then, Brooks has informed Kelly that both he and Winthrop are creditors of Moore, and that Robinson improperly transferred assets from Moore’s trusts.
“I deny the allegations contained in the amended complaint, most especially the notion that anything that I did in furtherance of my obligations to Winthrop caused the death of Drue Moore, and I intend to vigorously defend against all allegations,” Robinson told Sportico in an email. He said Winthrop is currently “engaging independent experts and consultants” to maintain continuity of the company’s operations.
No attorney has yet appeared on Brooks’ behalf in the case, which was originally filed in early February and first reported on by Law360. Winthrop, which is also named as a defendant in the suit, is being represented by Gary Shipman, the North Carolina-based lawyer and sports agent who recently sued the NCAA on behalf of an NC State football player seeking a fifth year of eligibility.
“Our job is to undertake the independent representation of Winthrop, which will include a proper investigation of the allegations made in the amended complaint, including, but not limited to, whether funds have been diverted from Winthrop by anyone,” Shipman told Sportico in an email. “We are also in the process of engaging others that will be called upon to exercise independent judgment about all of these matters and to insure [sic] the continued operation of the Company. We regret the tragic death of Drue Moore who, as the Complaint and Amended Complaint make abundantly clear, left more questions than answers.”
Shipman declined to say who was responsible for retaining him on Winthrop’s behalf but confirmed the company is his only client in the matter.
The current situation unfolds as a disturbing sequel to what had already resembled a Greek tragedy involving the men behind Winthrop and their families.
Colorado District Court Judge Lisa Arnolds, who presided over Ben Moore’s divorce in 2019, stated in her permanent orders that Ben and Drue Moore had both “colluded to hide assets from … this Court and the IRS.”
Specifically, Ben Moore had claimed that his 50% ownership stake in Winthrop had been transferred to a trust established by Robinson, allegedly to benefit his children, with Drue Moore serving as the trust’s protector. However, the judge ruled that the trust was “not bona fide” and had been created with the intent to fraudulently deprive Ben Moore’s ex-wife of her rightful share of marital property.
Six years later, Drue’s wife Kelly is now asking a North Carolina court to issue a declaratory judgement that she and her children are entitled to Drue’s 50% stake in Winthrop and that neither the company nor Brooks have a right to any proceeds from the decedent’s life insurance policy. The suit also seeks damages against Brooks and Robinson—who is identified as Winthrop’s “sole manager, president and secretary”—and other companies Robinson owns, due to claims of emotional distress, negligence, fraud, breach of fiduciary duty and unjust enrichment. Earlier this month, the case was assigned to a special superior court judge for complex business cases.
In addition to this lawsuit, Brooks is currently in separate litigation with his former attorney, Andrew Quait, over tens of thousands of dollars in unpaid legal fees. In late 2020, Quait represented Brooks in a federal breach-of-contract lawsuit filed against Ben Moore and his ex-wife, Amy Elizabeth, claiming that the couple owed him $3.2 million as part of a real estate transaction. Ben Moore quickly conceded a number of the allegations Brooks made against him, then used the forum to assert counterclaims against his ex-wife, before he and Brooks moved to dismiss the case in early 2021. Quait then accused Brooks of failing to pay him for much of the legal work he did on his client’s behalf through August 2021.
A Colorado court entered a default judgment against Brooks in 2022 for nearly $174,000, which has since grown to almost a quarter-million-dollars with interest. In an effort to collect on the damages, Quait is now engaged in a battle over a subpoena with Ben Moore for information about “the financial dealings and possible fraudulent conveyances” between the two men. Moore and his current wife, Julia, have sought to quash Quait’s subpoena, arguing that it is overly broad and was improperly served.
Meanwhile, Ben Moore faces an active bench warrant after being inadvertently released from jail prematurely last year while serving time for a remedial contempt charge in his divorce case. Quiat has referred to him in filings as a “a fugitive who apparently remains in contact with his multiple lawyers and is at times present in his residence with his current wife.” Moore is not named as a defendant in the suit filed by Drue Moore’s heirs, and the lawyer representing Julia Moore did not respond to a request for comment.
“A stop must be had to the continuation of habitual efforts to avoid and evade courts, including this court, from exercising their proper authority to hold Benjamin Moore accountable for his dealing with millions of dollars each year,” Quiat wrote in a Sep. 2024 motion. A hearing over the subpoena dispute is set for next Tuesday.
Despite the surrounding chaos and tragedy, Winthrop—which, in addition to WIN AD, maintains the college sports job website called Intercollegiate—gives the appearance online of a company functioning without distraction. Indeed, the company’s X account, which had not made a peep from November 2021 to May 2024, currently posts multiple times a day.
In her lawsuit, Kelly Moore suggests she has been in touch with both Brooks and Robinson since Drue’s death, that both defendants have provided starkly different accounts of the events that transpired since last year, and that she is not sure who, if either, to believe. Brooks, according to the suit, has suggested that Robinson had in recent months transferred a number of assets, including Drue’s ownership stake in Winthrop and the family home, out of the trusts and back to the company in order to pay off creditors who included Brooks. Robinson, according to Kelly Moore’s court filings, has maintained that no such conveyance occurred.
“Regardless,” the lawsuit states, “as a result of unbearable financial pressure placed upon Drue by Brooks and, if Brooks is to be believed, Robinson, Drue committed suicide, leaving Kelly and her two young sons to try to piece together the financial wreckage created by Drue’s business partner and personal attorney/trustee/business manager.”
Late last year, according to the lawsuit, “documents began to surface, allegedly written by Drue,” in which he purportedly confessed to the embezzlement allegations against him. However, the complaint raises doubts about the authenticity of these confessions, suggesting they may have been written by Brooks instead.
Kelly Moore informed the court that she has yet to receive any concrete evidence showing that Drue Moore took unauthorized distributions from Winthrop. In challenging the defendants’ credibility, she pointed to a history of dubious bankruptcies and lawsuits involving Brooks and the Moore cousins over the years.
Her lawsuit suggests at least some disconnect between what she knew of her husband’s business and financial dealings and the reality of the situation. For instance, she claims that in 2020, at Drue’s direction, she signed the deed to their residence over to two Wyoming LLCs set up by Robinson, despite not fully understanding the purpose or nature of the transaction.
Robinson declined to say who is currently running Winthrop. However, on Jan. 22, he signed the one-year renewal of Binghamton University’s WIN AD software services agreement, according to a copy of the deal obtained by Sportico.
Three days earlier, a memorial service was held for Drue at a church in Durham. Ray Purpur, Stanford’s deputy athletic director, was the first of the mourners to speak. His voice trembled as he reflected on his long-time friend: “It’s a moment I never imagined would come,” Purpur said.
He fondly recalled Drue’s love for winery tours, fine dining, hiking, family vacations and sports. “As we honor the fullness of Drue’s life,” Purpur added, “we must also recognize the struggles he faced. Like all of us here, Drue carried burdens—burdens that, in the end, became too heavy to bear.”
