Former Racing Jockey Jimmy Winkfield was the winner of the Kentucky Derby twice in 1901 and 1902, and is the most recent Black Jockey to win the celebrated race. Due to segregation he left to ride in Europe, but in the early 1930s he worked at the Rock as the house Maître d’.

When Jimmy first arrived at the Rock Rest he noted the stone structure and marble bar and quipped “This sure is a solid place to rest your elbow!!” And so it has been ever thus.