This isn’t to suggest that the Red Sox shouldn’t plan ahead for a future with Betts. He’s one of the best players in baseball and one of the best the franchise has seen in decades. We should want to see Betts wearing a Red Sox uniform for the rest of his career.
There’s just no reason to commit to that now. Too much can change over the next two years. A career-altering injury could derail his value before the extension even kicks in. He could revert to his 2017 level at the plate instead of the batting champion we saw this year.
Extending Betts now would be paying for his peak value coming off his MVP season. We always hear warnings about teams shelling out massive deals to free agents after a career year. Ask the New York Yankees how the Jacoby Ellsbury deal is panning out for them. If overpaying for a potential outlier season is risky, doing so when the player is under team control for two more years is downright foolish.
The only advantage of an early extension would be if there was an opportunity for a bargain. If Betts wanted to lock in long-term security now, he could sign an extension for below market value. The Red Sox get a superstar on a team-friendly deal and Betts protects himself against the career-crippling worst-case scenario.
Except Betts has made no indication that he’s willing to accept a hometown discount or play it safe by signing early. Boston could offer him the moon and Betts may still decline, preferring to wait and see if the market for superstar players hits new highs two years from now.
By agreeing to an early extension, Betts risks missing out on a bigger payday down the line if other stars raise the bar in the next couple of years. Locking him up now at current market rates potentially saves Boston a few million bucks in the long run but not without the risk of the contract becoming an albatross soon after the extension kicks in. It just doesn’t make sense for either side to make that commitment two years before they need to.
Boston’s best option is to let Betts play it out his way, then negotiate a new deal based on his perceived value in two years. There’s some risk that he could bolt to a rival team if given the chance to test free agency but the Red Sox need to trust that their winning culture, leadership, and a city he has come to embrace will be enough to entice him to stay.