Under the current ownership group the Boston Red Sox have been forced into some difficult financial decisions. They've had to part ways with some of their most popular stars an best players rather than strap themselves down into a pricey more importantly lengthy deal. Such is the case with ace lefty Jon Lester at least that's how it seems. However if the Sox fail to sign the All Star hurler they could be making a huge mistake.
Let's first start with the basics. Jon Lester has started 30 or more games every season since 2008. In that time he has won 99 games. His ERA this season is at a steady 2.50. The man has been a playoff beast. In fact his World Series ERA in three starts 0.43 with wins in three of those games.
Yes he is now 30 which seems to be the Sox brass's biggest hang up. In 2005 the same ownership group let beloved ace and future Hall of Famer Pedro Martinez walk rather then pay him 80 million over 4 years. A move that proved to be the right decision. However Pedro had noticeably begun to decline. Although among the leagues best when healthy, the problem was he struggled to stay in good health and that kept him off the mound. Not the case with Lester. That same off season the Sox allowed another All Star Derek Lowe leave for LA.. Lowe was far more effective over a longer span of time then Pedro and also was a matter of a long term deal.
Now ten years later the Sox have their ace for the last eight or nine seasons up for a new contract. Boston insulted Lester in the spring with a 4 year $70 million deal. In comparison Home Bailey signed a 6 year $105 million deal. Which is close to what's going to take to keep Lester. I must admit I'm not fan of giving a guy a six year deal at the age of 30. However this would be one of those risks I'd consider worth taking when you consider his history.
Boston has been rumored to be discussing a deal with Philadelphia for their high priced left ace as a suitable replacement for Lester this off season. Hamels is also 30 however yet he is only under contract for the next four years for around $80 million. Which as I mentioned has been the Sox fiscal plan as of late. Over pay for a short term deal rather then strap on a long term agreement.
Hamels is a quality arm for sure and only this season has had injury woes. However Philadelphia is not just going to give him away. A deal to bring Hamels to Boston will take at least three top prospects and possibly a major league ready arm like a Workman or Dubront. That's just as an expensive price tag over the long term as Lester would be if you just paid him and kept your prospects. In fact presumably those prospects you would have traded for Hamels would be major league ready right about the time the Lester deal would be wrapping up.
Also consider were with almost absolute certainty Lester will end up if and when the Sox fail to sign him. As sure as George Steinbrenner is in the ground the NY Yankees will offer Lester every bit of $110 million plus. The Yanks would love to once again have a dominant lefty in their rotation especially one with almost no baseball related injury history.
Ultimately it makes far more sense from every angle to keep Lester, to keep your prospects and your leader day after day in your rotation. Just one year removed from his second World Series crown Lester's numbers are better then ever. Since mid June this season only Clayton Kershaw has a better ERA than Jon Lester. He is a much ingrained in Boston as Ortiz or Pedroia. Although the fan base will recover if he walks and so will the Sox eventually the evidence is clear the intelligent move is to resign him.
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