He’s made no indication (that I have heard) that he in any way prefers to hit free agency rather than stay in Boston. There didn’t seem to be any love lost over the arb proceeding this year. He said in ST that he won’t talk about it during the season, which is common and completely understandable.
He has, and is, betting on himself (and he’s up big). Did people really expect him to sign an extension after a season which was, by many, considered underwhelming? With an off-season expected to set records coming up?
He’s young, exciting, does everything, and will age well. He’s a franchise player. Holy shit guys, Dave Dombrowski is the GM, not Ben Cherington. If I were a betting man I’d say it gets done eventually, but probably after Mookie has pushed the price close to market.