Mookie Betts won an MVP and a World Series with the Red Sox, yet he wasn't able to come to an agreement with the club on a long-term extension. He was traded with one year left before free agency to the Dodgers, who have now come to a massive contract extension with him.
This deal obviously shakes up the free agency outlook after this season, with Phillies catcher J.T. Realmuto becoming arguably the most coveted free agent on the market this winter. That got us thinking, will a similar scenario surface with any current stars who are closing in on free agency and don't seem far down the road on extension talks? Here are five names I came up, in order of the likelihood it happens.
Francisco Lindor is a legitimate superstar and isn't going to sign with Cleveland long term. The owner even said last year to the fans of the club to basically enjoy him while they can. Great messaging, right? He's only controlled through 2021 and surely they will trade him before he hits free agency instead of just letting him walk. It's unclear at the moment what large-market team will take a stab at Lindor, but if it happens, you can bet they'll work on a monster extension, given the likely hoard of prospects he'd cost.
Kris Bryant recently made some comments about how absurd it is that some have the idea he wants out of Chicago. That he hasn't gotten an extension yet and that Scott Boras is his agent seem to weigh heavily in public opinion. It might not be Bryant's choice, though. The Cubs are heading toward a financial apocalypse. Mike Axisa outlined as much when ranking the Cubs dead last in terms of financial flexibility this coming offseason. If the Cubs fall out of the race quickly this year, bet on Bryant being dealt. If they don't, I'd still bet on it this coming offseason. One scenario I can't shake: The Cubs deal Bryant to the Phillies -- where he joins his buddy Bryce Harper -- and nearly immediately extend him with a giant deal.
Yes, another member of the Cubs nucleus. Willson Contreras is one of the best offensive catchers in baseball with a rocket for an arm. It looks like his framing -- the only negative in his game -- is set to be much improved this season, too. So why would the Cubs trade him? See above on the financial situation. My hunch is unless they make a deep playoff run this year, the position-playing core is blown up with only Javier Baez and people like David Bote remaining. That makes Contreras the second-biggest trading chip and someone like, say, the Mets would love to have him and extend him.
The Rays aren't dealing Tyler Glasnow anytime soon, but he has three arbitration years left after 2020. If he continues to pitch like he did last year (1.78 ERA in 12 starts), he's gonna get awfully expensive and we know they don't like that in Tampa Bay. He's young enough that it would make sense for a big-market team to deal for him with, say, two years left before free agency and then would try to extend him.
The Athletics have done so in the past, most notably spinning Josh Donaldson to the Blue Jays. This would be trickier, however, as Semien is set to hit free agency after this season and he only became a star last year, jumping from 4.7 WAR to 8.9. It doesn't seem likely the A's will fall out of contention fast enough to justify dealing a cornerstone, but if they do fall out, Semien goes.
