Why Jon Lester Re-signing With Red Sox is Far From a Sure Thing

Aug 21 9:59am


Starting pitcher Jon Lester hasn’t been shy about his desire to stay with the Boston Red Sox for the long-term. Contract negotiations were cut off in Spring Training when the organization offered a four-year, $70 million extension and Lester’s representation wanted something more in the $100 million range.

Lester didn’t want to negotiate during the season, considering it a distraction. That didn’t seem to be a problem — the Red Sox were coming off a World Series victory in 2013 and planned on competing again this year with him at the top of the rotation. Once the season finished, there would be an exclusive negotiating window for the two sides to utilize to strike a deal before he hit free agency.

Well, that plan has backfired.

Boston is currently 56-70 and 17.5 games out of first place in the AL East — the complete opposite of what they were expecting in 2014. General manager Ben Cherington decided to sell at the non-waiver trade deadline, including shipping Lester to the Oakland Athletics in exchange for Yoenis Cespedes. Before getting dealt, Lester was open about still coming back to Boston next season, even after a trade was completed. While that’s still a possibility, that will be far from a sure thing once the winter hits.

It’s clear the A’s won’t be a player for Lester after the 2014 season is complete. This deal was a rental to help them get over the hump and win a World Series title.

Not accepting Boston’s extension offer in the spring led to him bet on himself this year with the hopes of pitching well enough to get the contract he wants. He’s certainly done that. Lester has been a fantasy baseball stud on the mound, posting a 13-8 record with a 2.58 ERA, 1.11 WHIP and 174 strikeouts in 170.2 innings pitched. If his ERA and WHIP numbers stay around where they are now, the will far and away be new single-season marks for the hurler.

Upon hitting the open market, his price will continue rising since he’s a legitimate ace that nearly every team would covet having, even though he’ll be  31 years old next year. Teams have shown they’re willing to overpay a player at the end of their career to get prime production at the beginning of a contract.

Jon Heyman of CBS Sports reports a return to the Red Sox is a long shot, despite the left-hander saying he’s open to coming back.

The reasoning here is Boston needs to significantly increase their offer to be competitive with other interested teams, which Heyman identifies as the New York Yankees and Chicago Cubs. There’s no doubt Lester felt a little disrespected with that Spring Training extension offer from the Red Sox. Even though the organization is looking into the future with regard to how he’ll produce on the mound, he wants to get compensated for what he’s already done, which has included being a crucial piece of two championship teams.

Fair enough, but it makes his future in Boston more foggy than originally expected.

Heyman suggests the bidding could get as high as $150 million for six or seven years, meaning Cherington must more than double the money and nearly double the years they originally offered to reach those numbers. That’s a huge jump. Considering the types of contracts they’ve handed out in recent years, it’s not the type of deal they like having on the books. It’s possible he’ll still take a “hometown” discount to return, but it still has to be more than four years and $70 million.

So, Red Sox Nation shouldn’t rejoice about the eventual return of Lester just yet.

Outside of the Cubs and Yankees (who are seemingly in on every high-priced player), the Dodgers and Mariners are teams that stick out to me. Los Angeles has the finances to afford Lester, and they’re looking for another ace to add to its pitching staff. They engaged the Phillies in trade talks briefly about Cole Hamels, after all.

The Mariners have a lot of money on the books to hand out — mostly to Felix Hernandez and Robinson Cano — but they’re not afraid of making a big splash. Born in Tacoma, Washington, it could attractive for the southpaw to come back to his actual home and pitch for a team that’s playing a lot better than anyone expected.

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