I keep reading it is cycylical, but Philadelphia has no trouble drafting great players late in the rounds (which they usually trade for vets).
1. Awful drafting and developing in the minors (mostly pre-Bill Smith) has led to not one legit MLB player coming up in three years. Unreal.
2. Not signing Santana and/or Hunter when they had the chance, and your GM just quitting and handing the job to someone not ready for it.
3. Lack of any outside newcomers into the organization. They are stuck in their processes, and not improving over time. Typical big company issue.
4. Horrible trades by Smith. Just awful. Unreal how bad they were.
5. cutting the payroll in year three of a new stadium.
6. Ridiculous preferences for certain types of players (Butera types) that actually decrease the odds of winning the more they play.
7. Injuries to your best players, on a thin team, you can't afford this. (including minor leaguers)
8. Bad allocation of resources (with a limited payroll, you need to spend correctly, not on "proven closers")
9. Horrible use of the DL, leaving the bench thin over and over and over, year after year (an example of lack of external thinkers causing group think).
As for spending money on Mauer showing they are willing to spend money....no. Willingham is the biggest FA contract they've ever given, ever. They cut payroll this year.