In 2012, the Rangers signed Ian Kinsler, an inferior player to Pedroia, for 5 years and $75 million. This was an extension of his previous contract and replaced a $10 million option year with a $13 million guaranteed year (last year). The extension was for his age 30-35 seasons. I think that is the starting point of what Pedroia would fetch on the open market. The top end of course is Cano's 10 year $240 million contract which takes him to his age 40 year.
People who don't think Pedroia's contract is a bargain are people who think too hard to make good things into bad things because they need to worry about something.
Seriously, I'm all for new threads, but the idea that because he hasn't hit for as much power as SoSH likes for two months, Cherington might regret that contract is pretty crazy. There is literally no new information available to us since the contract was signed that would make you change your mind. I guess people like Savin probably didn't like the length at the time of the signing either and would have proposed higher AAV for less years, so if your opinion is consistent, great. Although in practice, the same arguments that the Red Sox wouldn't bench Pedroia apply for whether they would re-sign him when the shorter contract expired. If they aren't cold enough to waive Dustin if he becomes a terrible player, why would they be cold enough not to re-sign him if he wanted to stay when he was, say, age 35?