Beyond that, who knows?
Way back in March, Betts' response to Mike Trout's record-setting $426.5 million contract extension with the Los Angeles Angels was to tell reporters he didn't anticipate reaching his own agreement with the Red Sox. His focus was on hitting the open market after 2020.
It would be a nice silver lining on the Red Sox's deeply disappointing season—they've slipped from 108 wins and a World Series in 2018 to 81 wins and no playoff berth in 2019—if Betts was changing his tune in the final days of the campaign.
But according to separate reports from ESPN's Joon Lee and Alex Speier of the Boston Globe, neither the ouster of president of baseball operations Dave Dombrowski nor the Red Sox's recent homages to franchise legends David Ortiz and Carl Yastrzemski have shifted Betts' stance.
Betts' position is best summed up by something he told Lee: "I love it here, but definitely it's still a business."
Though some Red Sox fans might not appreciate Betts' indifference toward his legacy in Boston, he need not schedule an apology tour.
According to Baseball Reference, Betts has racked up more wins above replacement since 2014 than every position player except Trout, who's making more money just in 2019 ($36 million) than Betts has in his entire career ($33.6 million). Factor in his role in last year's championship run, and Betts has provided the tea Red Sox with far more value than they've paid him for.
If the Red Sox want Betts to stay in Boston and take his place among the organization's all-time greats, it's up to them to make it happen. To this end, their only hope of swaying him is in making him an extension offer worth far more than the measly $200 million proposal he rejected after 2017, per Joel Sherman of the New York Post.
Can the Red Sox afford that? Probably. After all, the franchise is worth $3.2 billion, according to Forbes.
However, whether the Red Sox want to pay Betts is another matter.
The organization was hit "hard" by the luxury tax in 2018—those quotation marks are necessary because a $12 million penalty and a 10-spot drop in the 2019 draft order hardly constitute a staggering blow—and it's on track to be hit again this year. Rather than continue to put up with this, the Red Sox have a "significant desire" to cut payroll and reset their luxury-tax penalties, according to Speier.
Signing Betts to a mega-extension is at odds with this goal. For that matter, said goal doesn't mesh with simply keeping him for his final season of arbitration eligibility. After earning a $20 million salary for 2019, he's all but certain to break Nolan Arenado's record-breaking $26 million arbitration payout next season.
Meanwhile, the Red Sox also have their farm system to consider. It began the year ranked as the worst in MLB, and it ended the year in the exact same spot.
Hence the big question that invariably creeps into any discussion about Betts these days: Is he destined to be traded?
Per Jeff Passan of ESPN, the Red Sox will "at the very least listen" to offers for Betts this winter. If so, they'll presumably accept any offer they can't refuse.
That should be doable on account of Betts' extraordinary ability. At his best, he posted a 1.078 OPS with 32 home runs, 30 stolen bases and 10.9 WAR in 2018. Otherwise, it says a lot about his baseline talent level that he's put up a .911 OPS, 28 homers, 16 steals and 6.5 WAR in a "down" 2019 season.
However, Betts' looming free agency and likely $30-ish million salary for 2020 complicate his trade value. Ideal trade partners for the Red Sox are clubs with talent and cash to spare and their sights set on World Series glory in 2020. Few organizations check all three boxes.
There's also a shortage of precedents for a Betts trade. The most relevant deals from recent history are ones in which Justin Upton (2014), Jason Heyward (2014) and Paul Goldschmidt (2018) were moved before their walk years. That none of the three netted an outrageous haul of talent potentially doesn't bode well for Boston's leverage with Betts.
If a package of players worthy of Betts' talent isn't forthcoming, the Red Sox might still trade him to avoid his huge 2020 payout. But such a deal would amount to a salary dump, which would be difficult to justify unless the circumstances were just right.
For instance, maybe the Red Sox will find out Chris Sale does indeed need Tommy John surgery on his ailing left elbow. They could also lose J.D. Martinez if he opts out of the final three years of his five-year, $110 million contract and signs with another team in free agency.
Sans Sale and Martinez in the picture, 2020 would suddenly look like a transition year. There would be no better time to satisfy the team's luxury-tax goals, in which case a Betts trade would be a necessary evil.
Then again, the Red Sox might have Sale get a clean bill of health and Martinez opt in. That would line them up for another World Series run in 2020, which would be that much more likely to succeed if they kept Betts around. Boston would just have to concede that getting under the luxury-tax threshold could wait another year.
If all else fails, the Red Sox could punt on trading Betts. This would involve taking a wait-and-see approach to 2020 in which they might look to move him ahead of the July 31 trade deadline. His list of suitors might only grow between now and then.
Ultimately, "It depends" is the only right answer to the question of what the Red Sox should do with Betts. Even if they can't extend him this winter, they should only trade him if the price is right. And even then, they wouldn't necessarily have to move him. At least, not yet.
Confused? Good. That means you have a sense of just how difficult a position the Red Sox are in with their brightest star.
Stats courtesy of Baseball Reference.