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It comes down to how much how much you think a guy is worth currently, and how you think he'll decline in correspondence with how you think the market is going to develop in the future.
$15mil over 5 for Bay basically gives him '07 market FA value in the short term, and expects him to hold his value or decline minimimally unless the market recovers strongly. Its just a bad gamble.
I expect average GMs to pay $3.5-4.5mil per W this offseason, and I except skilled GMs to find the bargains (Z, Epstein), and unskilled GMs to overpay (Bavasi, KC types).