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Mazz: Theo Had Negotiation Edge Over Red Sox For Jon Lester

BOSTON (CBS) - "I can assure you, and I don't know what Lester was thinking, but neither Lucchino nor Epstein wanted to lose to the other." - FOX Sports' Ken Rosenthal

As a Red Sox fan, losing out on Jon Lester hurts. And if you're a member of the Red Sox organization, it hurts even more losing the sweepstakes to former protege Theo Epstein and the Chicago Cubs.

Aside from money of course (the Cubs offered $20 million more), 98.5 The Sports Hub's Tony Massarotti believes Chicago had a distinct advantage over the Red Sox in signing Jon Lester.

Namely? Personality.

"If you're sitting at a table across from the Red Sox ownership and management, who do you believe in? [Owner] John Henry is awkward. [President] Larry Lucchino? He's a lawyer and comes off like he's trying to screw you at every paragraph. Or [general manager] Ben Cherington, who you look at and say, 'Well this guys got no juice because the other guys are pulling the strings.' Which one of those guys do you look at and believe in? None of them," said Mazz. "That's where Theo had an edge in this thing, because he knows how the Red Sox operate."

Jeff Passan of Yahoo! Sports was the first to break the Lester story, and there's an interesting note in his article that lends some credence to Mazz's take.

"The thing I liked about 'em is it wasn't forced and wasn't a sales pitch," Lester said after his meeting with the Cubs. "It was like, 'This is what we can do.' I don't want BS. I don't want show. I don't want glitz and glamour. I don't want to walk out to the field with your name and number on the JumboTron. I'm not 18 anymore. I want you to tell me what you can do for me and my family."

Communication skills is a key factor in a negotiation. And that skill is something Epstein possesses, whereas the Red Sox brass does not.

"Epstein loves Lester, and he would sit down with Lester and know how to communicate with him, and understand what makes Lester tick and what would be effective in delivering a message and making an offer. Theo knew what Lester would respond to because he has that sense that the Red Sox don't. He's got better people skills than they do. He can make you feel like he's telling you the truth even when he's lying -- it's a gift. The other guys can't. They don't come off that way; it just fails. If Theo had any advantage in this thing other than money, that was it. Theo can close deals."

Listen below to the full discussion!

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