Money does grow on trees in professional sports. All you have to do is look at contracts that teams dole out every season that make fans scratch their heads and swear at their computers until steam shoots out of their ears.
While researching the teams and their contracts, one thing has become evident. If you sign more than a couple players to bad contracts, the odds are the list will continue to grow. Teams like the Mariners, Dodgers, Rangers, Tigers and Yankees have been notoriously bad in spending their money. The Yankees can afford it. The Mariners and Rangers can't.
On the other hand, teams like the Marlins, Padres, Pirates, Twins and Astros have been on the opposite end of the spectrum. I suppose it's easy to spend your money wisely if you pretty much ignore trying to sign virtually any free agents. That's one approach.
There is not only a lot of debate about the worst contract for each team, but even more for the worst contract of all-time in MLB. I focused on each team leaving the "all-time" question up for future debate.