The dentist whose promotional photos caused problems for a UNC basketball player in 2013 died over the weekend.

Spencer Howard was a graduate of the dental school at the University of North Carolina at Chapel Hill and the founder of Iceberg Holdings, which designed custom mouth guards for athletes. One of those athletes, Leslie McDonald, appeared in advertisements for the company, prompting UNC to issue him a cease-and-desist letter.

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Leslie McDonald (2) cracks a smile during the North Carolina Tar Heels vs. Florida State Seminoles NCAA basketball game, Saturday, March 3, 2013 in Chapel Hill, NC.

Howard died over the weekend near his home in New York, where he moved after a succession of legal and ethical troubles in North Carolina.

In November 2016, Howard permanently surrendered his North Carolina dental license after reaching a settlement agreement with the state for Medicaid fraud, including a finding that he had fraudulently billed $1 million in anesthesia services.

After losing his license, Howard filed for Chapter 7 bankruptcy, listing debts that included a $1.3 million mortgage, $16,800 due in past taxes to the City of Durham and a $30,000 lien from the IRS.