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Curt Schilling on D&C: ‘I can’t imagine’ Red Sox will sign Jon Lester to long-term deal

11.14.13 at 11:46 am ET
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ESPN’s Curt Schilling  joined Dennis & Callahan on Thursday morning to discuss the MLB offseason, the Red SoxWorld Series title and the results of the Manager of the Year vote.

The AL Manager of the Year was announced on Tuesday, as former Red Sox and current Indians manager Terry Francona narrowly edged Boston manager John Farrell, with just 16 points separating the two skippers.

“It was hard,” Schilling said. “I thought the American League one was incredibly challenging, because I thought you had a bunch of guys that had phenomenal seasons. … I thought either one of them could have won it. I think the job that they both did was amazing.”

The offseason is in full swing, as the annual GM meetings have kicked off in Orlando. The Sox already have been linked to multiple players, including Carlos BeltranBrian McCann and Carlos Ruiz.

One storyline that has been discussed is what the Sox will do with pitcher Jon Lester once he enters free agency after the 2014 season. If Lester is able to post another great campaign in 2014, the southpaw could command a long-term deal worth over $100 million.

“I think if [Ben Cherington] is allowed to do the things that baseball ops people should be allowed to do and there’s no interference from people that shouldn’t be interfering, I think he’ll stick to [his previous offseason plans],” Schilling said. “You’re not going to see another eight-year, $240 million deal out of this organization, and rightfully so. … There’s literally almost maybe two or three guys in the history of the last 25 years that would have played to [$200 million-plus contracts]. He can’t do it.

“I can’t imagine they would [sign Lester to a six- or seven-year, $100 million-plus deal]. I don’t think you’ll see any team other than probably the Dodgers with [Clayton] Kershaw turn around and give their homegrown player six or seven or eight years, I don’t see it, not from this team anyway. You saw what happened when they tried to go down that path, and I think that is going to be fresh in their minds as long as these guys are still making decisions here.”

Boston’s run to a World Series championship in 2013 seemingly shocked everyone in New England, as Boston finished last in the AL East with 69 wins just a year prior. While some have argued that the ’13 championship has been the most unexpected title in recent years, there are many, including Schilling, who believe that the ’04 title was still more improbable.

“I disagree wholeheartedly with that,” Schilling said. If you look at that team in ’04, the talk of baseball was the Yankees, and it became improbable the day we lost 19-8 [in Game 3 of the 2004 ALCS]. There was a human part of me at the end of this where I was kind of thinking, ‘Wow, you know, if they win, it’s going to take away from what we did. It’s going to make what we did mean less.’ And then I was so excited for them because of how they did it and what happened and I realized nothing will ever change in ’04. There will never be another ’04.

“Coming back the way we came back from down 3-0 and doing it the way, we win in those eight straight games. I mean, that was as improbable a scenario as I’ve ever been put in. … This [title] was improbable for different reasons. … It was an amazing story for a lot of good reasons. Nothing bad had to happen for this to happen to them.”

To hear the interview, go to the Dennis & Callahan audio on demand page. For more Red Sox news, visit the team page at weei.com/redsox.

Read More: AL Manager of the Year, ben cherington, Curt Schilling, Jacoby Ellsbury
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