BOSTON (CBS) – Red Sox ace and opening day starter Jon Lester is certainly worth way more than the $13 million the team is paying him now, but if he hits free agency he’ll likely get way overpaid, which is why Michael Felger and Tony Massarotti feel like they need to be “very careful” in doing this contract extension.

The two sides, although amicable at the moment, have walked away from the negotiating table and are pausing the discussions for now.

Lester, 30, is in the final year of his contract and is willing to take a “hometown discount” in order to remain in Boston beyond this season.

With the way Jon Lester backed off those initial comments about a hometown discount, Tony Mazz thinks the two parties are farther apart than they’d like to be, and this is likely attributed to the market getting “even more player friendly” this offseason.

If Lester is looking for a Cole Hamels deal (six years $144 million), Mazz thinks that’s a scary area to be in if you’re the Red Sox.

“If he gets on the market I don’t think they’re gonna match. I’ll tell you that right now. I don’t know that I would give him [Cole Hamels’ deal]. If it goes six years I want this year to be part of it, you know, five in addition to this. But the more I think about it, five years and $110 million is the number. $22 million per. Five years. That’s it. I doubt he’d do that because I think he can get more than that on the market. If it comes to that, I think you let him go. I think you do. It’s crazy, but I just don’t think it makes sense to pay pitchers in their mid-to-late thirties $22, $24 million a year.”

Felger is of the same mind as Tony in wanting to limit the amount of years on the extension. Anything over five years is pushing it, but maybe to get the player you sweeten the pot and increase the average annual value (AAV). If Lester’s not budging on the higher AAV and shorter term deal, then Felger says it’s time to say sayonara.

“I don’t think that’s crazy at all. If I’m the Red Sox, and I’m living by my word of being disciplined, I don’t sign that kind of deal for Jon Lester. I’m not going any farther than five years and $115 million. That’s it. He’s 30. Do I think he would sign for that? No. Do I think he would get more on the market? Yep. He’s gonna get more than that. Max Scherzer just turned down six years and $144 million because he knows there’s more out there. Lester is gonna make more and he knows it, and if I’m the Red Sox I don’t pay him. Play out this year, maximize everything you can out of the player, have him pitch one more year to get that contract and take the draft pick.”

Now what the Red Sox should do and what the Red Sox will do are two very different things, so listen below for the full discussion and 2014 season preview:



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