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"Lester was drafted by Theo's predecessor"
True. All your other points are valid, but at the end of the day the guy put together a roster that won two World Series trophies, and that meant a lot when their franchise hadn't won one in 86 years.
That'll end my defense of Theo. My head is starting to hurt.
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Espein drew a pretty good team when he took over the Red Sox's. He had Ramirez and Martinez in their prime. Nomar was having his best year and Damon and Trot Nixon were more usefull then any of the outfielders the Cubs have. Adding Ortiz in 2003 and Schiling in 2004 was really all the team needed. Then Youkilis came along and added another power bat. To fix the Cubs is going to be alot more difficult. They dont have the solid base to build on. Trying to buy that solid base in the free agent market is what got them in trouble the first time. Adding a grade A free agent to a good team can make a GM look really smart. Adding one to a bad team doesnt.