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Shapiro can't be seen as giving up while we've still got a realistic shot at the division. We're 5.5 back of the Twins. We play them 8 more times, 6 of them at home. Nonetheless, if we're 7 or 8 back at the all-star break, I think he'll start to shop his moves.
What happens when the plug is pulled? The best bet is that Finley is dealt. I don't follow the minors so I don't know who is available but Boston would love to have him, assuming Chuck continues to perform well. It would also fit with old George's style to sign him just to keep Boston from getting him. That would be cool: a bidding war between boston and NY for finley.
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The time to pull the plug is at the deadline. Let the Sox and Yanks battle it out for Finley until the end. Someone might overpay for him.