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I don't know that we can really know much of what Jack & Co really want in a ballclub yet. It wasn't just a time crunch that they were dealing with - it was also a $$ crunch. They didn't exactly spend much of that $90 million on their own players. They had a lot of holes to fill and no $$ to spend.
When you've got almost $20 million of that $90 million tied up in two pitchers that had a net negative impact on the team (Silva and Batista), you are going to be in trouble almost no matter what. This off season will give us a much better read on what these guys value.
I will say that I still don't see a lot of budgetary reality in the M's blogosphere. Give Felix a blank check. Sign Webb. Add two or three "big bats" for LF, 3B and DH. I just don't see all that happening. As much as we might want to M's to run a Red Sox payroll, it's just not going to happen.
If I were to hazard a guess, I would guess that we are going to get a Felix extension and a Gillick off season - two or three $5-$8 million players. It's all going to come down to Jack - can he find an Olerud and a Boone or will he stick the franchise with underperforming players?