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

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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. “I think we blew the signing [of Jon Lester] in spring training,” Henry said last month.

Hey, live and learn, right?

But somebody has to say it: Henry and the Red Sox have made another mistake with a lefty ace, Chris Sale, this time with an outsized $145 million, five-year extension on top of the $14.5 million he will make this year. In the current context, in the current market, it appears to be a significant overpay and an assumption of enormous risk.

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