Charles Timothy O’Leary
Born: 10/15/1882- Chicago. IL
Died: 1/6/1941- Chicago, IL
Each World Series that I’ve replayed has included a small biography of a player that is participating in that particular World Series. I don’t generally choose Hall of Famers, or the more noteworthy players, but someone that I either have prior knowledge of, or someone I don’t know anything about. Sometimes I find a diamond, sometimes I find a rock. When I saw Charley O’Leary on the 1907 Detroit roster I immediately jumped on him because I knew he would be an interesting story. After all, his mother owned the cow that kicked over the lantern that started the Great Chicago Fire in 1871. That’s a great piece of trivia, not everybody knows that story, this will be a pretty cool biography. Was I in for a surprise.
Charley O’Leary was a member of my Cleveland Spiders Diamond Mind internet team that I had several years ago. He was a serviceable shortstop that seemed to hit better than his real-life stats, so he was a favorite of mine, and besides, his Mother’s cow started the Chicago fire.
When I started to do the research I soon realized that the infamous Kate O’Leary was not Charley’s Mother. Kate O’Leary had just 1 son, James Patrick O’Leary and Charley was one of 16 siblings. Yes, they were both from Chicago, and yes, they were both buried in Mount Olivet Cemetery, but they were not Mother and son, and they were probably not related at all.
I knew that the O’Leary cow story was an urban legend, I knew that Kate O’Leary was a real person that became a scapegoat for the fire, and I knew Charley O’Leary was her son. I was so certain that this was a fact. How did that piece of misinformation enter my brain? Memory is a strange thing.
Charley O’Leary was born in Chicago, and his family may or may not have owned a cow, but he honed his baseball skills playing semi-pro ball in the Chicago area. He may have signed with the White Sox, but had his arm broken by a pitched ball from Rube Waddell in an exhibition game. But like Mrs. O’Leary’s cow this may be more fiction than fact.
He did sign with the Detroit Tigers and made his debut on April 14, 1904. He played 135 games at shortstop, committed 54 errors and batted just .213. An inauspicious beginning, but he would be the starting shortstop for the Tigers for the next 3 seasons. He would hit .213, .219 and .241 with 55 and 58 and 48 errors at short. Consistent, but mediocre.
A fan favorite for his antics on and off the field. He teamed with Germany Schaefer during the off season to perform in a vaudeville style comedy act.
O’Leary had a career year in 1907 hitting a robust .241 with career highs of 34 rbis and 19 doubles. He helped lead the Tigers to the 1st of 3 straight AL pennants. He would hit just .059 in the World Series against the Cubs, getting just 1 hit in 17 abs. In 3 World Series he would hit just .128 with 5 singles.
O’Leary would play 5 more seasons with the Tigers in a part time roll, playing both 2nd and short. He would appear in 65-75 games per season and would hit between .203 and .266.
After playing in just 3 games in 1912 he would move over to the NL and play 1 season with the St Louis Cardinals. In 121 games he hit .213 and would retire at the end of the season, finishing with a .226 lifetime average and just 3 home runs.
After retiring O’Leary joined Miller Huggins’ coaching staff on the Yankees, and would coach in 6 World Series with them. He would also coach for the Cubs and the St Louis Browns.
While coaching for the Browns he would appear as a pinch hitter on the last day of the season, singling and scoring a run at the tender age of 52 in 1934. That one I know is fact……..I think.






