Boston Red Sox cannot afford to make mistake with Chris Sale

Chris Sale is slated to be a free agent at the end of this coming season. The Boston Red Sox cannot afford to let him go.

Let us go back in time to the 2014 season. The Boston Red Sox were coming off of a World Series victory, and their staff ace was set to reach free agency at the end of the year. Jon Lester had been an important part of that championship, with a solid performance in 2013 and an excellent postseason. Lester allowed just one run in 15.1 innings in the World Series matchup with the Cardinals, a dominant showing as the Red Sox won the title.

Understandably, the Red Sox were looking to extend Lester. Their offer – four years at $70 million. Whether or not that was meant to be the starting point for their negotiations, Lester and his representatives ended those talks. After a midseason trade to Oakland, Lester ended up signing a six year deal worth $155 million with the Cubs, more than doubling the Red Sox offer.

Today, the Red Sox face a similar situation with Chris Sale. They are once again coming off of a World Series victory, defeating the Dodgers in five games. Sale also had a solid regular season, and was the front runner for the Cy Young award before injuries derailed his second half. He was not nearly as dominant in the postseason, but he did record the final outs in Game Five, striking out the side to clinch the World Series.

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Just like Lester, Sale is in his walk year. At 30 years old just after the regular season begins, he will be a year younger than Lester was when his free agency was approaching. However, Sale may be a more important part of the rotation than Lester ever was, his resume far superior to what Lester had accomplished. A seven time All Star and the all time leader in K/9 and K/BB rates, Sale is establishing himself as one of the greatest pitchers in the game.

That status makes is all the more important for the Red Sox to extend Sale, and to do so quickly. He is a true ace, the type of pitcher that any team would love to have atop their rotation. Even after the free agent freeze of the past two offseasons, Sale would be a hotly sought after commodity if he came available.

The Red Sox cannot afford to find themselves in a bidding war for his services. They have the opportunity to lock Sale up into a long term extension, as his representation has yet to set a deadline for those talks to end. Sale himself has mentioned being open to an extension, leaving the ball firmly in the Red Sox court.

The Boston Red Sox blew their chance to lock up Jon Lester five years ago. They face a similar situation with Chris Sale this year, and cannot afford a similar mistake.