There are few individuals who have been associated with the Orioles for as long and deeply as Rick Dempsey. Many younger fans know him from MASN broadcasts and as the namesake of Dempsey’s Brew Pub and Restaurant in the Warehouse. But he spent parts of 12 seasons as the Orioles catcher and later served the club in several assistant coaching capacities. While Dempsey’s on-field performance earns him his ranking on this list, it is long-time association with the Orioles and his goofy antics that fans remember most.
Half of John Rikard Dempsey’s 24 major league seasons as a player were spent in Baltimore.