Major League Career
Dempsey was selected by the Minnesota Twins in the 15th round of the 1967 Major League Baseball Draft out of Crespi Carmelite High School. After two seasons in the minor leagues, he made his major league debut late in the 1969 season for the divison winning Twins managed by Billy Martin, however he didn't qualify for the post-season roster. Dempsey spent a few more seasons shuttling between the Twins and their minor league teams, before being traded to the New York Yankees in October 1972. During his tenure with the Yankees, he served as a reserve catcher to Thurman Munson, and received tutoring from Yankees coach and former catching standout, Jim Hegan. After three and a half seasons with the Yankees, he was traded to the Baltimore Orioles in June 1976, where manager Earl Weaver made him the Orioles' starting catcher.
For the next ten and a half seasons, Dempsey would remain as the Orioles' starting catcher. He became known for his exceptional ability to handle pitching staffs, his strong throwing arm, and for his agility behind home plate. In 1979, the Orioles defeated the California Angels in the 1979 American League Championship Series to reach the World Series. In the 1979 World Series, the Orioles won three of the first four games against the Pittsburgh Pirates and seemed to be on the verge of winning the championship, when the Pirates, led by Willie Stargell, rebounded to win the final three games. It was one of Dempsey's greatest disappointments of his playing career.
The highlight of his career came in 1983, when the Orioles won the American League Eastern Division pennant, then defeated the Chicago White Sox in the 1983 American League Championship Series, before winning the 1983 World Series against the Philadelphia Phillies. Dempsey posted a .385 batting average along with a .923 slugging percentage in the five-game series, and won the World Series Most Valuable Player Award, one of six catchers to have won the award.
In 1987, Dempsey became a free agent and signed a contract to play for the Cleveland Indians. After only one season with the Indians, he became a free agent once again and signed with the Los Angeles Dodgers, where he would be a member of another World Series-winning team in 1988, this time as a back up catcher to Mike Scioscia. While playing for the Dodgers in 1990, he became involved in a brawl with Phillies' center fielder Lenny Dykstra, who took exception to Dempsey's fraternization with the home plate umpire. After three seasons with the Dodgers, he played one season with the Milwaukee Brewers, before returning to the Baltimore Orioles for his final season in 1992.
His sense of humor during his playing career was renowned, and he was famous for his "rain delay theatre" performances, in which he emerged from the dugout in stockinged feet onto the tarpaulin covering the infield during a rain delay and pantomimed hitting an inside-the-park home run, climaxed by his sliding into home plate on his belly on the wet tarp, all to the raucous delight of the soggy fans. He sometimes did this while wearing a pair of underpants over his uniform, making fun of teammate Jim Palmer's famous advertisements for Jockey brand briefs.
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