Pedroia signed his extension on July 24, 2013 and there was an
article by Gordon Edes and Kyle Brasseur published that same by ESPN that has the following:
According to John W, Henry, "Pedroia first approached the club about an extension in spring training of 2012." The article says, "Henry said he was taken aback when Pedroia approached him with three years still left on his deal" and that he was concerned they weren't serious about trying to re-sign him. Henry said, "I think in his mind the best way to do that is 're-sign me early,' and thankfully that's what we were able to do."
There is also discussion about, "In the wake of the Crawford and Gonzalez experience, the Red Sox had expressed an aversion to contracts of such length (seven years in both cases). Lucchino said, "What we have ruled out is the kind of long-term, gigantic commitment to players, if at all possible. We're not going to set a hard-and-fast rule that says nothing will ever be done along the following lines. We'll always have some kind of exception to a general presumption."
Given some of the unfortunate and bad decisions the front office has made in recent years in signings/trades, they have ended up driving the luxury tax penalties to higher than needed levels and also haven't built up the farm system, especially from a pitching point of view. They are at a point now when they will have to bury themselves under the luxury tax to re-sign their best player (and one of the very best currently in MLB) because clubs aren't willing to give up Boston's asking proce for a player who will become a free agent after the season ends. In the past, they might have found a contending team to trade with as the season is winding down, one that perhaps has not been in post-season for a while and feels that Betts is the missing piece; however, the trade deadline is now July 31st. So what do they do? Take the best offer of the most and best young talent they can get for him before the deadline and start rebuilding.
My personal feeling is that the Players' Union and MLB should get together and redesign things, starting with money. MLB should tell the players, "Here is your half of the money. Divide amongst yourselves as you see fit." That should keep the players busy over the winter.