Charles Comiskey is remembered today mostly as the skinflint owner of the 1919 Chicago Black Sox. The Hall of Famer was so much more.

Comiskey’s association with baseball started when he debuted as a first baseman for the St. Louis Browns in 1882. The following season he became player/captain/manager and reeled off four American Association pennants and one World Series title in 8 years.

After hanging up his uniform in 1894, Comiskey played a key role in founding the American League in 1901. As owner, his White Stockings played in the inaugural AL game.

An autograph collector reached out to Comiskey in September, 1914 looking for The Old Roman’s autograph. In the collection is Comiskey’s response that reads in part, “I am herewith enclosing you autograph as per your request, with assurances that I am delighted to  send this.”

Comiskey then affixes his signature in large and bold lettering at the bottom of the letter.

Hall of Fame outfielder Harry Hooper witnessed some memorable baseball moments during his 17-year big league career. A four-time World Series champ with the Boston Red Sox, Hooper was part of Boston’s “Golden Outfield” along with Duffy Lewis and fellow Cooperstown man Tris Speaker.

In the collection is a four-page letter from Hooper answering questions about how he wants to be remembered, what it means to be a Hall of Famer, and the makeup of his all-time team.

Shown above is one page from Hooper’s musings. Here he gives his thoughts about the 1919 Black Sox scandal and the role that Chicago owner Charles Comiskey had in in. Responses to the other queries can be read by clicking here.

About the Chicago gambling fiasco Hooper writes, “There were some who were unjustly punished, notably – Joe Jackson and Buck Weaver.” Hooper then assigns some of responsibility to the White Sox owner. “I believe Comiskey was guilty of fomenting the deal by his refusal to pay his players in line of what other players were receiving on other teams.”

An interesting take from Hooper whose Red Sox club finished 20 1/2 games in back of Comiskey’s White Sox in 1919. Powerful content indeed from a man who was active in the big leagues at the time of one of baseball’s worst incidents.

The previous letter in which Harry Hooper offered his opinions on the Black Sox scandal and Charles Comiskey’s role in it  arrived in this envelope. Notice Hooper’s signature in the return address portion. This question was one of only 8 queries that Hooper wrote about. His insightful reflections about the feeling of being a Hall of Famer, how he wants to be remembered, and the choices for his all-time team can be seen on Hooper’s page by clicking here.

Handwritten letters from men who played more than 100 years ago remain highly valued by collectors and fans alike.