Cliff Fleet fined $500 for crash that seriously injured student

Cliff Fleet ’91, M.A. ’93, J.D. ’95, M.B.A. ’95 at 2022 Convocation. RYAN GOODMAN / THE FLAT HAT
Cliff Fleet ’91, M.A. ’93, J.D. ’95, M.B.A. ’95 at 2022 Convocation. RYAN GOODMAN / THE FLAT HAT

Colonial Williamsburg CEO and Immediate Past Chair of the William and Mary Foundation Cliff Fleet ’91, M.A. ’93, J.D. ’95, M.B.A. ’95 addressed the Class of 2028 Saturday, Aug. 25.

Just three months prior, Thursday, May 30, he was fined $500 for striking Rosemary Raynal ’25 with his SUV in October 2023.

Williamsburg Commonwealth’s Attorney Nate Green J.D. ’98 told The Flat Hat in April that he did not know if the charges, if any, would be presented to a grand jury. Green later recommended the reduction in charges.

“So, if the priority is to treat a case as consistently or as similarly as other like cases, a summons or an arrest warrant would be expected,” Green wrote in an email to The Flat Hat. “However, if the priority is to minimize the number of times a witness would have to attend court, an indictment presented to the Grand Jury would be considered.”

The Daily Press first reported that the charge against Fleet was reduced from reckless driving, a Class 1 misdemeanor that carries a penalty of up to 12 months in jail, to improper driving. Fleet pleaded no contest and was fined the maximum amount — $500 — by Williamsburg-James City County General District Court Judge Joshua DeFord.

The College of William and Mary Board of Visitors member and former Virginia Senate Republican Leader Thomas Norment J.D. ’73 served as Fleet’s attorney.

“He has never reached out to see how Rosemary was doing. He has never said he’s sorry,” Ann Brooke Raynal, the student’s mother, told The Daily Press in May. “I understand that accidents happen, and I believe this was an accident, but a brave man finds a way to own up to his mistakes. Period.”

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