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++ If you sink big bucks into a Teixeira, and then scrounge for the other 3 slots - IMO, you've wasted your money, because you cannot afford to fail twice, (and that includes having ANY of your re-signed talent swoon). ++
They're not going to fail.
You trade Carlos Triunfel, you have Matt Tuiasosopo, you have Dustin Ackley, you have under-valued ML vets (like Branyan) and you have an almost infinite variety of options.
You keep up with the trial-and-error until you get a 95 OPS+ on the cheap.  And Halladay keeps ringing the cash register for you.
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YOUR POINT IS CORRECT in that if that's what was going to happen -- you were going to wind up with a 140 Bedard and a 60 CF -- you wouldn't PLAY Stars & Scrubs.  But that's not what happens.  It's easy to upgrade a 60 player.
What happened when the Mariners traded Adam Jones?  How long did it take to find a good Scrub CF?
Would you rather have Adam Jones, Chris Tillman and Ryan-Rowland Smith RIGHT NOW?   Or Franklin Gutierrez, Brandon Morrow and Erik Bedard?
Play some roto, San my man.  ;- )  You'll see.