History tells us extending a massive contract to a superstar too early can be risky, which should make the Red Sox hesitant when it comes to Mookie Betts.
Let’s get this out of the way early. The Boston Red Sox will not sign Mookie Betts to a long-term extension this winter. He’s going to get a one-year deal, either by reaching a mutual agreement or through an arbitration hearing, then follow the same path next year before hitting free agency in 2021.
It’s not that the front office isn’t interested in locking up the reigning American League MVP. We can’t criticize Dave Dombrowski for “failing” to get a deal done when the player has no interest in sitting at the negotiating table. Betts has made it abundantly clear that he’s willing to bet on himself, going through the arbitration process year after year until he earns the right to test free agency.
Calm down, this isn’t a sign that Betts is eager to leave Boston. It’s simply the path he sees as the best option to maximize his earnings. He’s right to assume that, so long as he believes in his ability to play at this elite level between now and free agency.