Released from the Pirates, Cronin joined the Detroit Tigers, then in the Class-A Western League in 1899. On September 18, 1899, the Cincinnati Reds of the (NL) purchased Cronin from Detroit. In April 1900, they returned Cronin to Detroit, now a member of the American League.[1]
Cronin was released by the Tigers on June 8, 1902, and he signed with the Baltimore Orioles that same day. However, the Orioles struggled with debt. Joe Kelley, star player for the Orioles and son-in-law of part-owner John Mahon, reported that the team owed as much as $12,000 ($422,585 in current dollar terms).[2] Unable to afford that debt, Mahon purchased shares of the team from Kelley and player-managerJohn McGraw. With this, Mahon became the majority shareholder, owning 201 of the team's 400 shares.[3] On July 17, 1902, Mahon sold his interest in the Orioles to Andrew Freedman, principal owner of the Giants of the NL, and John T. Brush, principal owner of the Cincinnati Reds, also of the NL. That day, Freedman released Cronin, Kelley, Dan McGann, Cy Seymour, Roger Bresnahan, and Joe McGinnity from their contracts with Orioles. Freedman signed Cronin, McGann, Bresnahan, and McGinnity and to the Giants, joining McGraw, who had signed with the Giants ten days earlier. Brush signed Seymour and Kelley to the Reds.[4][5]