MLB's Biggest Offseason Questions: Gerrit Cole, Red Sox and the Deep Freeze

With the World Series behind us, it's time to shift our attention forward on what's to come in the offseason.

Welcome to the start of baseball’s grand annual roster recombobulation period. We’re still less than a week out from Game 7 of the World Series, but the decision deadline for many options has already passed, and free agency starts in earnest today, November 4. It’s officially the offseason—so get in the spirit with a rundown of the questions most likely to be asked (and, with any luck, answered) in the next few months. ‘Tis the season!

Will 2020’s market move as slowly as 2019’s did?

The 2019 free agency class was defined by the act of waiting as much as it was by Bryce Harper and Manny Machado. The proverbial hot stove was cold for months. Machado signed in the last week of February; Harper in March; Dallas Keuchel and Craig Kimbrel in June. The freeze—which could be seen in 2018, too, not just 2019—has established itself as a pattern, and it’s set on an entire structure, rather than a few specific player-and-team situations.

131 Players Become XXB Free Agentshttps://t.co/Msxx4Pl3n4 pic.twitter.com/OMIPjin9Nm

— MLBPA Communications (@MLBPA_News) October 31, 2019

Which is the crux of the answer here: The structure is still the same. MLB’s collective bargaining agreement does not expire until December 2021. There has not been any grand adjustment in the macro-scale player-pay system, which means that, in all likelihood, there won’t be any grand adjustment in what we see from free agency. Of course, it’s possible that watching the slow crawl of the last few winters has left its mark on players and teams and resulted in a tweak in process from one side or both, and we do see something notably different. 

But... don’t bet on that. (Especially not now that there’s a precedent of teams working around draft picks tied to the qualifying offer by simply waiting to pick up a player until after the draft.)

What’s the market for Gerrit Cole?

Okay, now onto the fun stuff.

Cole seems almost a lock to become the best paid pitcher in the game—whether you’d prefer to define that as topping Justin Verlander’s $33 million average annual value or David Price’s $217 million total contract (or both!). Cole just turned 29. He has a 2.68 ERA with a 13.1 K/9 over the last two years. He can do this. All four of his pitches have the potential to be brilliant, and for a multi-month stretch in the middle of 2019, he looked like one of the best starters that baseball had seen in recent memory.

Gerrit Cole, Fastball, Knuckle Curve & Slider Spins. pic.twitter.com/7m2bLI9mlG

— Rob Friedman (@PitchingNinja) October 6, 2019

While it does not seem particularly likely that the pitcher chooses to remain in Houston, it does seem reasonable to believe he’ll become the most handsomely paid in baseball. The real question is by how much.

Will Stephen Strasburg stay in Washington?

Hours after the Nationals’ World Series parade, Strasburg announced he was opting out of the $100 million and four years remaining on his deal in D.C. Given how he pitched this year, that was hardly surprising—he can likely command far more on the open market than he would have gotten from the extension he signed in 2016. (Especially when you factor in that a decent chunk of the money left on that extension was deferred, and therefore less in real value.)

Like Gerrit Cole, Stephen Strasburg made himself an extraordinary amount of money this season. Between his NL-leading 209 innings and his incredible playoff performance, Strasburg looking at a deal that exceeds his original $175M contract with the Nationals. That’s the floor.

— Jeff Passan (@JeffPassan) November 3, 2019

Yet opting out doesn’t necessarily mean that the pitcher will leave the Nationals. While he’ll certainly have other suitors (including, reportedly, his hometown Padres), there’s still reason to believe that the Nats are open and Strasburg is potentially interested.

The Nationals’ rotation is solid enough that they could withstand the loss of Strasburg. But why would they want to if they didn’t have to? And on Strasburg’s side—while there’s any number of unknowable personal preferences involved in each individual free agency—it’s hard to ask for a sweeter situation than a team that’s well-positioned for the future and fresh off the World Series. There’s certainly no guarantee, but Strasburg’s opt-out may just end up as a chance to opt back in.

What about Anthony Rendon?

If there was any doubt about where Rendon stood in the pantheon of best third basemen in MLB, there shouldn’t be after this year. His walk season was his best yet (153 OPS+ and 6.3 bWAR), and it seems reasonable to think about a deal in the vicinity of Nolan Arenado's eight-year, $260 million extension with the Rockies. The question is where. The Nationals certainly shouldn’t be written off; they reportedly offered him a hefty extension as late as September, so the interest is clearly there. It just may also be that there's just as much interest from the Rangers, or the Phillies, or the Braves, or an as-of-yet mystery team.

Will new Boston GM Chaim Bloom trade Mookie Betts?

Bloom’s introduction as Red Sox new lead baseball executive came with a clear directive: Get the team under the luxury-tax threshold. (To be fair, Red Sox president Sam Kennedy has labeled this as a “goal, but not a mandate,” but when this kind of thing is being explicitly discussed by executives in public at all... it’s bound to seem at least a little mandate-y.) He’s also tasked with building up the farm system. And he has Mookie Betts.

Introducing #RedSox Chief Baseball Officer Chaim Bloom! pic.twitter.com/FMggoT2HoN

— Red Sox (@RedSox) October 28, 2019

Trading Betts would mean dealing a talented and beloved star from a currently competitive team. That’s generally not the kind of move that’s widely embraced—but if the primary goals are shedding salary and adding prospects, Betts may offer the best path that the Red Sox have available to them. (If still a cynical one that offers a harsh look at the team’s priorities.) In trading the 27-year-old outfielder, Boston would almost certainly bring back a monster prospect package and cut payroll at the same time. All they’d have to do is give up their best player.

This will be a revealing—if rather unenviable—first quandary for Bloom as GM.

What about players who took pillow contracts last winter?

Yasmani Grandal, Josh Donaldson, Dallas Keuchel, Mike Moustakas: All inked one-year contracts for 2019, ostensibly with the goal of landing something better for 2020, and whether they do or not should provide an interesting year-to-year comparison for the market.

Each built a fairly solid case for himself with this last season. Grandal further established himself as one of the best catchers in baseball. Donaldson reminded everyone what he can do when fully healthy. Keuchel is still a quality mid-rotation arm, and Moustakas is an above-average hitter who can move around the infield. Just how much those cases pay off, of course, is a very different questions from just how good those cases are.