Rich people are rich (except NBA players) because they generally don't get involved in red-cost ventures. That's why teams have budgets. It's really easy for you to sit here as a fan and say "WELL I DONT CARE IF MARK A LOSES MONEY I WANT A CHAMPIONSHIP", but clearly, he is not going to choose to operate that way. He got rich by not operating that way, and there's nothing suggest that he's going to change the way he manages his money. Just so long as we all understand it is a choice he is making. It is not as if he cannot afford to sign more players, he's choosing not to. Personally I care a lot more about the Brewers winning than I do whether Mark A ends up worth $100 million or $1 billion! It's not that simple, though; his budget is set at a certain amount. He's operated his entire life with a budget and not breaking it means that he's been able to live the life he's set out to. People that save a lot of money, make a lot of money, etc, tend (not always, obviously) to have very strict budgets for themselves. For them, "afford" means not breaking their budget, even though they might be able to comfortably afford things out of their budget. They have a status quo, and they don't stray from that. So while you say he has a choice - he does, and maybe he can "afford" to buy better players, but in the realm of his business world, he cannot afford them without risking loss. We don't have to like it, but it makes sense for him.