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Rick began his Major League career with the Minnesota Twins in 1969. He was traded to the New York Yankees in 1973 where he played until 1976. In 1976 he was traded to the Baltimore Orioles as part of a 10-player swap that brought the Orioles Rick, Tippy Martinez and Scott McGregor. He became the Orioles starting catcher in 1977 through 1986 catching a club-record 1,222 games. After leaving the Orioles, Dempsey played for Cleveland in 1987, Los Angeles Dodgers 1988 to 1990 and the Milwaukee Brewers in 1991 before returning to the Baltimore Orioles for his final season in 1992.

Rick ranks 21st all-time with 1,633 games caught at the Major League level where he boasted a .988 career fielding percentage. Rick played in three World Series in 1979 and 1983 with the Baltimore Orioles and 1988 with the Los Angeles Dodgers. Rick is a two-time World Series Champion. He was the named the World Series MVP in 1983 for the Orioles and caught the final out of the 1988 World Series for the Dodgers. Rick was elected to the Orioles Hall of Fame in 1997.

After Rick's playing career he managed in the Minor Leagues for five seasons in the Los Angeles Dodgers and New York Mets Minor League systems. Rick was a coach on the Major League staff with the Los Angeles Dodgers in 1999 and 2000. In 2001 he went back to Baltimore and took an analyst position with Comcast SportsNet. From 2002 to 2006 Rick served as a coach on the Orioles Major League staff. His duties included first base coach, third base coach, catching coach and bullpen coach.

After his Major League coaching career concluded Rick became a pre-game and post-game analyst for the Baltimore Orioles on MASN through the 2020 season. Rick has been a staple in the Baltimore community since the mid 70's helping at thousands of charity events, golf outings, auctions, baseball clinics, running a restaurant at Camden Yards and speaking to various groups, schools and businesses. Through Rick's performance as a player and many contributions to Baltimore off the field he has become one of the most beloved Baltimore sports figures of all time.

Rick and his wife, Joani, live in Westlake Village, a suburb of Los Angeles. They have two sons, John, who was a catcher in the St. Louis Cardinals organization, and Christian. Rick’s younger brother Pat was a Minor League catcher for several teams, including the Baltimore Orioles. His nephew, Gregg Zaun, is a former Baltimore Orioles catcher.

Rick has been involved with The Baseball Warehouse for many years through camps, coaching clinics and speaking to players and their families on the many different facets of baseball. Rick is opening his own TBW training facility in Columbia, MD where he will offer private lessons, camps, coaching clinics, sports performance, facility rentals and much more.