A 1906 Chicago Baseball Champions Gold and Diamond Medallion Presented to Cubs Outfielder Billy Maloney

Awarded to Cubs outfielder W.A. “Billy” Maloney after the club’s victory over the Chicago White Sox in the 1905 City Series, this remarkable piece represents an early chapter in Chicago’s storied baseball rivalry. The postseason matchup, created in 1903 by White Sox owner Charles Comiskey and Cubs president James Hart, was designed to determine the true “Champion” of the Windy City. In total, 26 City Series were contested through 1942, each intensifying the competitive divide between Chicago’s two major league clubs.

Maloney (1882–1960) was a member of the Cubs during one of the most dominant stretches in franchise history. An outfielder known for his steady defensive play and dependable bat, Maloney lead the National League in stolen bases in the 1905 campaign, tying the Giants’ Art Devlin with 95.

To commemorate Maloney’s contribution to the Cubs’ 1905 City Series triumph, he was presented with this 14-karat gold medallion. The design incorporates Chicago’s familiar municipal “Y” device, symbolizing the branching of the Chicago River, accented by a baseball and crossed bats. At the Wolf Point intersection within the design rests a single old European-cut diamond weighing approximately 0.25 carat.

The reverse is engraved, “Presented to W.A. Maloney By National Commission.” Measuring just over one inch in diameter, the medallion stands as a tangible reminder of one of the earliest and most spirited chapters in Chicago baseball history.


Gross weight: 9.85 dwt. Accompanying chain is made of silver.

This lot is located in Chicago.