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Charles Comiskey was a big league first baseman from 1882-1894 in the American Association, Players’ League, and National League. Many credit him with revolutionizing the position. The custom of the day was to stay close to the bag at first. Comiskey popularized playing off the bag to cover more ground.

In 1883 Comiskey became player-manager of the St. Louis Browns. He led them to four straight American Association pennants, winning it all in 1886. At each stop for the rest of his playing career, he would also manage.

Comiskey finished his 13-year playing career with 1,529 hits, , 992 runs, 883 RBI, and a .264 batting average. In his managerial career that spanned from 1883-1894 Comiskey guided teams to an overall record of 839-540 record, good for a .608 winning percentage. From 1885-1888 Comiskey’s American Association St. Louis Browns won four straight pennants.

Shown here is Comiskey’s reply to an autograph request. This letter dated September 13, 1914 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.

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After his playing career ended in 1894, Charles Comiskey invested into the new Western League by buying the Sioux City, Iowa Cornhuskers. The same year he moved them to St. Paul and changed their name to the Saints.

In 1899 he relocated the team to Chicago and called it the White Sox. At the same time, the Western League rebranded itself as the American League. Two years later the AL declared itself a major league.

Comiskey’s White Sox were immediately successful. They won the first American League championship in 1901 behind pitcher-manager Clark Griffith. Five years later they upset the crosstown Cubs to win the 1906 World Series.

Comiskey constructed a new stadium in 1910 that hosted baseball for the next 80 years. His reign is best remembered for the powerhouse 1919 team that threw the World Series against the Cincinnati Reds.

Comiskey kept control of the team throughout his life. When he passed in October, 1931. His son J. Louis Comiskey inherited the team. The younger Comiskey ran the team until heart disease claimed his life in 1939.

Upon his death, a legal battle resulted in J. Louis’s widow Grace Comiskey gaining control. In 1941 she became the first female president in American League history.

Grace ruled the team until her death in 1956. Ownership then passed to Grace’s daughter Dorothy who was also the granddaughter of Charles and the daughter of J. Louis. Dorothy put the team up for sale in 1958. When Bill Veeck gained control of the White Sox in December of ’58, it ended the Comiskey reign.

Shown here is a document that consummated the 1935 trade of pitcher George Earnshaw from J. Louis Comiskey’s White Sox to the Brooklyn Dodgers. It is signed at the bottom by Comiskey and Dodger owner Stephen McKeever. Their signatures are seldom seen as Comiskey died in 1939 and McKeever passed in ’39.

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The American League’s first pennant-winning team was the Chicago White Sox owned by Charles Comiskey. That 1901 team was managed by Clark Griffith who was also their star pitcher.

As skipper he made all the right moves during the season. On the hill Griffith claimed a team-high 24 wins, leading the new league in winning percentage and shutouts. At bat he hit .303 with a .446 on-base percentage.

Shown here is a letter from Griffith dated November 16, 1943 and typed on Senators letterhead that lists him as team president. Griffith writes about that 1901 campaign.

“Yes, I managed the White Sox in 1901 when we won the pennant. The lineup of the team was Isbell, first base; Mertes, second base; Sugart shortstop; Hoffman (sic), third base; Jones, centerfield; Hoy, left field; McFarland, right field, Billy Sullivan and Joe Sugden were the catchers; and the pitchers were Patterson, Callahan, Griffith, Platt, and Katoll.”

Griffith’s bold signature is found at the bottom of the letter.

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Today Charles Comiskey is best remembered as the owner of the 1919 Chicago Black Sox that threw the World Series. His reputation as a cheap owner unwilling to pay his players is a myth.

According to contract cards at the Baseball Hall of Fame, the Opening Day payroll of Comiskey’s squad was $88,461 – more than $11,500 higher than the NL champion Cincinnati Reds. Four of the AL’s 15 highest-paid players were Comiskey’s men. Despite this, that narrative persists that Comiskey’s cheap ways caused the episode.

The scandal resulted in the banning of eight players by Commissioner Judge Kenesaw Mountain Landis. The most famous among them was outfielder Shoeless Joe Jackson.

During the Series hit .375. His 12 hits established a Fall Classic record that stood for 45 years. Jackson’s supporters point to this hoping for his reinstatement.

Many believe Jackson’s career is worthy of consideration for induction into the Hall of Fame. In more than 5,500 career plate appearances, Jackson hit .356 with a .423 on-base percentage and a .517 slugging percentage. Those numbers rank among the baseball elite.

Today more than a century after the memorable Fall Classic Jackson remains ineligible for Hall of Fame consideration .

In the collection is this government postcard from 1949. Jackson received many autograph requests in the mail from fans. Unable to read and write, Jackson has his wife sign his name. Even examples like this one hold value in the collectable market.

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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.”

Hoopers thoughts are not based in fact. According to contract cards at the Baseball Hall of Fame, the White Sox Opening Day payroll was in the top half of big league teams and more than $11,500 higher than the NL champion Cincinnati Reds.

The letter provides an interesting take from Hooper whose Red Sox club finished 20 1/2 games in back of Comiskey’s White Sox in 1919.