The argument that the MLB higher ups make regarding his gambling on his team to win is that anytime he didn't bet on them at all would be the same as hedging his bets against a loss. It is a slippery slope. If he bet for them to win on a Sunday but didn't bet on them at all on Monday, it is an advertisement that he felt they would lose. If anyone else had that information it could influence a betting line. And as far as I know, baseball is completely against gambling. They don't even want guys filling out March madness brackets in the clubhouse.