After beginning his career as a teenager with the Kansas City Monarchs of the Negro Leagues, this baseball player would go on to become the greatest Chicago Cub of all time. Known for his effervescent personality, he was a devastating hitter at the plate, becoming the first shortstop in history to hit $40$ home runs in a season and $500$ in a career. He also is the first National Leaguer to win consecutive Most Valuable Player Awards, which he did in $1958$ and $1959.$