Bob.
While I agree the Howard extension may be a "bad contract" production vs value. One of the prospects traded for pence was blocked by Howard. The pitcher the phillies gave up is one of 3-4 very good pitching prospects in A ball.
The 2 ptbnl are not going to be top prospects.
I'm curious to see what you mean by other "bad contracts"?
Halladay and Lee's deals may out last their top caliber production by 1 season. Other than that, there's no one besides Howard locked up long term.
The team has a had an ownership group not willing to spend Money, but they're all dying off and Middleton an owner who recently sold his cigar company for over a billion dollars is taking more control.
He wants to be George Steinbrenner or mark Cuban. He's not afraid to buy talent.
The "window" you speak of goes as far has the
luxury tax ceiling.