I don't think the CEO analogy holds up very well. The CEO is announcing his purchase, and it's governed by regulation and monitored. His actions are known, and other investors are free to decide whether they want to invest along with him or not. For a similar situation, the CEO would be buying stock on the sly, hoping to parlay inside knowledge into advantages of when to sell. Perhaps making decisions that boost the stock in the short term, but hurt the company in the long term...similar to burning through your bullpen to win a game you have money on, at the expense of the next few days games, which you don't care as much about. If Rosé only bet on the Reds to win (which, lets be honest, is doubtful), it doesn't make it any less bad. His decisions as a manager still come into question, which is a situation no sport can allow. Even if untrue, the perception that he (or anyone) isn't making decisions in an honest effort to win is just as bad as the actual thing. That's why baseball has hardcore rules against gambling, and are very concerned about it. It's just about the worst thing that can infest a sport.