I think this is where Tito's value really shines through. He's so good at managing people that he's got these youngsters in the palm of his hands and there's a lot of mutual respect there.
At different times Lester, Pedroia, Lowrie, Lester, Delcarmen, and even firey guys like Youkilis and Papelbon have expressed their respect and admiration of Terry Francona. There's a strong sense that these players know that Tito has their back and I bet they give him more on the field because of that than they'd give, say, Ozzie Guillen (an example of a decent manager who wins games, but one who sets himself up as more of a taskmaster and less of a gentle but determined old uncle).
Would not be surprised at all if the unspoken part of why Pedroia resigned on the cheap is to keep working for his cribbage partner. And for that reason alone, I do expect Lester, at least, to sign an extension before the All-Star Break next year.