Sometimes, especially when you're in win now mode, this could be the best way to improve your team. Let's say one year some team has very good players at most of their positions, making it very difficult to upgrade their offense/defense. Also let's assume they have what will likely be a very good bullpen, but their starting pitching is absolutely awful. If the market for starting pitching is poor (but there are a couple very good FAs) and they can't strike a reasonable trade to upgrade, why not attempt to spend big dollars to put the team into contention?
Correct me if I'm wrong, but it seems like you guys implicitly assume that you can upgrade your roster by 1 win for 10 million dollars when it is of course a lot more complicated than that. The market doesn't have infinite players. Sometimes it might make sense to expect a loss in the future just like the deadline trades this year, I'm sure most people on this forum would agree.