You have to spend money to get a write off. The write off might be 50% of what was spent. I don't think rich people stay rich by losing money in their ventures. If someone owns assets that increase in value and are worth $billions, there's only tax paid if the gains are captured (by selling them). A lot of teams are businesses, the sole business of the owner(s). So they do try to make money. The $billionaire who owned the Nets a few years ago paid massive luxury tax. It stung him so bad he cut the payroll and ended up selling 49% of the team. While it's one thing to pay a few $million extra on the team, it's another to lose a 1/4 $billion in luxury tax alone, to defeat the CBA. To get that $.25B, the guy had to sell $.5B worth of assets, and had to pay cap gains/income tax on that.