~Germany Schaeffer 1876 (Orphans 1901-1902)
He was born in a town that boasted nearly 25% German heritage--Chicago, Illinois--and his parents were fresh off the boat immigrants. So naturally, he got the nickname Germany. He began his big-league career in his hometown, but really made a name for himself in Detroit. He was the starting second baseman for the Tigers in both of their World Series losses to the Cubs (1907 & 1908). Germany was known for his wackiness. He once stole second base to attempt to force a throw, allowing a teammate to score from home. When the catcher didn't fall for it, Germany stole first base on the next pitch, so he could try it again. Here's another colorful story from the Baseball Biography Project:
According to teammate Davy Jones in The Glory of Their Times, Germany announced to the crowd: "Ladies and gentlemen, you are now looking at Herman Schaefer, better known as 'Herman the Great,' acknowledged by one and all to be the greatest pinch-hitter in the world. I am now going to hit the ball into the left field bleachers. Thank you." Facing Chicago's Doc White, Schaefer proceeded to hit the first pitch into the left field bleachers for a game-winning homer. As he made his way around the diamond, Germany supposedly slid into every base, announcing his progress as if it were a horse race as he went around. "Schaefer leads at the half!" and so on. After hook-sliding into home, he popped up, doffed his cap, bowed, and said, "Ladies and Gentlemen, this concludes this afternoon's performance. I thank you for your kind attention."Germany Schaefer died way too young, from a hemorrhage at the age of 42. He had only been retired for about a year.
~Doc Miller 1883 (Cubs 1910)
The Canadian-born Miller got exactly one bat for the pennant-bound Cubs on May 4, 1910. He couldn't crack the Cubs lineup, and they needed pitching, so they traded him eight days later to Boston for pitcher Lew Ritchie. It turned out to be a good trade for both teams. Miller became the starting right fielder for Boston. He led the league in hits the following year and batted .333. Meanwhile Ritchie won 42 games over the next three seasons for the Cubs.
~Pat Perry 1959 (Cubs 1988-1989)
The Cubs got Perry in the trade that sent Leon Durham to the Reds. He was a member of the division champion 1989 Cubs team, but he was used sparingly out of the bullpen (19 appearances), and didn't make the post-season roster. They released him in December of that year. He did manage to win two games and save two games during his tenure with the Cubs.
~Dan Plesac 1962 (Cubs 1993-1994)
Plesac was a very effective reliever with the Brewers (a three-time all-star), and he was a workhorse out of the bullpen during his two seasons in his hometown of Chicago (he's actually from Crown Point, Indiana). After his career ended he moved into broadcasting. For a few years (2005-2008) he was the studio analyst for Comcast in Chicago, but he has been with the MLB network since 2009.
A/V Club
Dan Plesac was a very good reliever, but he also gave up over 100 homers in his career. This one by Cecil Fielder was probably hit the furthest...