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Buster's Buzz: Why Boston's Chris Sale extension was a mistake

Boston Red Sox owner John Henry did something admirable earlier last month, acknowledging the mistake he made as Jon Lester moved closer to free agency in 2015. If you recall, Boston lowballed Lester on an initial offer, $70 million, for less than half of what the left-hander eventually got from the Chicago Cubs, $155 million.

The Red Sox lost an ace with a strong postseason history in the prime of his career, without proposing anything close to market value. By doing that, they turned the offseason negotiation into a competition they were destined to lose.