Bill Belichick and his girlfriend, Jordan Hudson, expertly matched at the 2026 Kentucky Derby - and used their attendance at the iconic event to seemingly shade their haters. Belichick, 74, sported a pastel blue suit with a pale pink shirt and tie to Churchill Downs on Saturday, May 2. His outfit coordinated with the colors of Hudson's strapless gown. Hudson, 25, opted for a gown with a blue bodice and pink floral appliqués dotting the skirt. True to classic Derby style, Hudson topped off her look with a hot pink fascinator. "Not the first time we've trudged through the mud together.