No one should have any economic sympathy for *anyone* who owns a major league baseball team (or an any other pro sports team FTM) but IMO at least, it doesn't particular advance the argument to harp on the assets of any particular ownership because that isn't what makes the situation what it is. The Dodgers and Yankees aren't able to spend more money because their ownership groups are richer or theoretically able or willing to invest more, they can spend more because the team has more revenue. If Ilitch owned the Dodgers he'd probably be spending what the Dodgers spend now and if the Dodger's ownership group owned the Tigers they'd probably be spending more or less what the Tigers spend now. Or conversely if Ilitch still owned the Tigers but the Tigers were the team from LA, the Tigers would be spending what the the Dodgers do.
There simply are not 30 markets in the US where you can generate the kind of revenue that LA and NYC generate. Every other sports org recognizes that and makes a serious effort to normalize revenues across the league. As long as baseball doesn't, there is no ownership group that will ever be able to rescue the Pirates or Marlins, Detroit etc., from their revenue disadvantage.