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Rollie moved on to a new environment in Chicago that featured two of the most notorious drinkers in all of baseball, outfielder Hack Wilson and pitcher Pat Malone. In no time at all, Rollie became completely unhinged. The reporters soon noticed his bloodshot eyes and disheveled appearance. Manager Rogers Hornsby, hardly a friend to the ballplayers, somehow tolerated the mischief of his new catcher. Gabby Hartnett caught most of the games, leaving Rollie to play once or twice a week. Still, he was effective, batting .309 in sixty-six games.

It took Hornsby another year to tire of Rollie’s bad conduct. Before the start of the 1933 season, Hemsley went to the Cincinnati Reds in a five-player trade. Chicago received slugger Babe Herman in exchange for four players from the Cubs. Rollie floundered in his new environment, batting a feeble .190 in forty-nine games. He only made it to August before the Reds released him, putting his career in jeopardy.

In an exceptionally strange set of circumstances, the St. Louis Browns claimed Rollie. Certainly they needed help anywhere they could find it; however, their new manager happened to be none other than Rogers Hornsby. Why the former Cubs boss believed Hemsley could be of any help is puzzling. He had seen the outrageous behavior, the black eyes, the cuts and bruises, yet still wanted Rollie to catch for him.

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