Reese's nickname originated in his childhood, as he was a champion marbles player (a "pee wee" is a small marble). Reese was born in Ekron, Meade County, Kentucky, and raised there until he was nearly eight years old, when his family moved to racially segregated Louisville. In high school, Reese was so small that he did not play baseball until senior year, at which time he weighed only 120 pounds and played just six games as a second baseman. He graduated from duPont Manual High School in 1937.

Reese was a strong supporter and good friend of the first ever black Major League Baseball player, Jackie Robinson. He was serving a stint in the Navy when the news of Robinson's signing came. Although he had little or no experience interacting with minorities--according to Reese, his meeting Robinson marked the first time in his life that he had shaken hands with a black man--he had no particular prejudices, either. It is reported that his father had made him starkly aware of racial injustice by showing him a tree where a lynching had occurred. The modest Reese, who typically downplayed his pioneering role in helping to ease the breaking of the 60-year-old color line, said that his primary concern with regard to Robinson's arrival was the possibility of Reese losing his shortstop job. Robinson was assigned to play as the team's first baseman, and Reese retained his position. Reese refused to sign a petition that threatened a boycott if Robinson joined the team. When a sportswriter asked Reese if he was threatened by Robinson taking his position of shortstop, Reese simply responded, "If he can take my job, he's entitled to it." When Robinson joined the Dodgers in 1947 and traveled with them during their first road trip, he was heckled by fans in Cincinnati. A myth has persisted that during pre-game infield practice at Crosley Field (the then-home of the Cincinnati Reds), Reese, the captain of the team, went over to Robinson, engaged him in conversation, and put his arm around his shoulder in a gesture of support which silenced the crowd. This incident however actually occurred in 1948 in Boston.[1] The gesture is depicted in a bronze sculpture of Reese and Robinson, created by sculptor William Behrends, which was placed at MCU Park in Brooklyn and unveiled on November 1, 2005. Throughout that difficult first year in the major leagues, Reese helped keep Robinson's morale up amid all the abuse. As the 1947 season wore on, there was tacit acceptance of the fact that blacks were now playing big league ball and were probably there to stay. Robinson still got pitches thrown at him, but, as Reese recounted to author Roger Kahn, "I told him, 'You know Jack, some of these guys are throwing at you because you're black. But others are doing it just because they plain don't like you.'" His role in nurturing Jackie Robinson aside, 1947 was a superb year for Reese, as he batted .284 with a league-leading 104 walks. He also had a career best slugging average of .426. Their rapport soon led shortstop Reese and second baseman Robinson to become one of the most effective defensive pairs in the sport's history. The friendship between Reese and Robinson is prominent in Roger Kahn's classic work, The Boys of Summer.

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