Some Reds fans may think of Pete Rose as being the first Reds player who experienced money and gambling troubles, but it seems as though the first traces of such date way back before even Rose came around in the organization.
Here are some excerpts taken from Redleg Journal:
February 5, 1919 - Former Reds first basemen Hal Chase is cleared of the charge of throwing games in collusion with gamblers during the 1918 season. The charge was brought against him by Garry Herrmann and Christy Mathewson. Chase was declared "not guilty" by National League President John Heydler, who studied evidence brought before him at a hearing held in New York City on January 30 in which testimony was heard from Chase, several Reds players and Herrmann. Mathewson couldn't offer any confirmation of Chase's alleged activities because he was still in France. Heydler contended that Chase's indifferent play the previous season was due to carelessness, and not the result of his betting against his club. Heydler had reason to reconsider this decision after the Lee Magee trial two years later. Magee's bid to return to baseball was thwarted by a Cincinnati jury who was convinced the charges against him of trying to fix a game in 1918 while playing for the Reds was true. During the trial, it was revealed that Reds players had placed multiple bets on the team to win in 1917 and 1918, but were never disciplined.
As fate would have it, the 1919 season turned out to be the last one in Chase's MLB career.
I found this little webpage which further details the transgressions of the 1918 Reds. I believe it may be of some interest to some historically-inclined Reds fans.
February 5, 1930 - The Reds trade Dolf Luque to Brooklyn for Doug McWeeny. On the same day, the Reds purchased Leo Durocher from the Yankees.
The 39-year-old Luque's best years were behind him, but he pitched six more seasons, primarily in relief. McWeeny only appeared in eight games with the Reds. But while the Reds lost a colorful character in Luque, they certainly gained one in the 24-year-old Durocher. A classic good-field, no-hit shortstop, Durocher rubbed Yankee veterans the wrong way and left New York with a mountain of debt. Leo's free-spending ways continued in Cincinnati, where he quickly became accustomed to night life in Newport. According to Reds historian Lee Allen, Durocher's nickname had not yet become, "The Lip." It was "C-note" because he always seemed to be in need of one. On more than one occasion, Sidney Weil bailed his shortstop out of financial predicaments.