Scattered Thoughts on the Chris Sale extension

In case you missed the big news on Friday, the Red Sox locked up their ace for another five years beyond 2019, agreeing to a five-year, $145 million contract extension with Chris Sale. It’s been a little under 24 hours since news first broke that this deal was at least close to getting done, and so we’ve had some time to sit with the excitement. Here are some scattered thoughts on the deal and some of the implications.

• First of all, I think this situation calls for a quick hell yeah. Whatever concerns there may be as well as ripple effects and other tangible effects, this is most importantly cool as hell. As we’ve talked about many times Sale is the most electrifying pitcher this team has had since Pedro and his starts are must-watch events. It would have sucked to lose out on that after this season, so if nothing else we are guaranteed another five years of Sale Days. That’s reason enough to celebrate.
• It’s awesome for us, and it’s also awesome for Sale. I think it’s fair to think that, as long as he doesn’t totally implode (either performance or health wise) in 2019, he was lined up to make quite a bit more than this in free agency. By committing to this deal, he is leaving money on the table. That being said, he obviously still has a lot of money in hand with this deal and he deserves every penny. He also doesn’t have to worry about potentially dealing with a long free agency as well as moving and everything else that comes with changing teams. Financial security and life stability is nice to have, and Sale has it now.
• If you’re going to find a reason to be concerned about this deal, you’ll likely point to the latter years of the contract. That’s the issue with any long-term deal, particularly for a pitcher who turns 30 in a week. Granted, Sale is not going to be super old by the end of this contract or anything, but the last year will be his age-35 season. Chances are he won’t be the same Chis Sale he is today at that point. So, yes, it is unlikely he provides great value for the length of this deal. Though, it should be pointed out that there is an opt-out after the third year. Opt-outs are always player-friendly, but we know they can be team-friendly if executed in the perfect way. This has a chance to be that, though it’s not something on which we should bank.
• That being said, he is going to be well worth it for the early years of his career, and that is how these contracts work. You pay for the up front production and live with a year or two of subpar. The Red Sox should get plenty of production on the front end of this deal, presuming health. Sale is obviously still an absolute monster and he hasn’t really shown any signs of slowing down when healthy. Plus, there is absolutely no guarantee he is going to have any serious or particularly precipitous decline. I am quite confident the good is going to outweigh the bad.
• The other concern here is the shoulder. Remember, this deal is technically not done as it is pending a successful physical. As of this writing (Friday night), that has not happened yet. Even assuming everything does come back clean, there is always going to be concern with that shoulder. It’s hard to really say too much about it since we don’t have a ton of information on the matter, but it’s just part of the deal here. Pitchers are always an injury risk, and Sale having dealt with that issue in 2018 is certainly scary. Not enough to make me dislike the deal, of course, but it’s something we’ll be thinking about for the duration of the contract.
• The player most affected by this deal has to be Rick Porcello. I don’t think anything is written in stone with any upcoming free agent for the Red Sox, but this would seem to make it more likely that Porcello will not be brought back after this season. I think that may have been likely before Sale’s extension ever happened, to be fair, but with Sale now locked up the Red Sox have a top four of Sale, David Price, Nathan Eovaldi and Eduardo Rodriguez. That’s already a fairly expensive group, and with other key position players set to hit the market soon I’m going to guess Porcello will be the odd man out.
• There’s been some talk over the last year or so about a closing window for the Red Sox. In my opinion that concept has always been overrated, as the Red Sox have the financial might to extend windows and keep them open indefinitely. That being said, having an ace locked in for the foreseeable future should quiet any concerns about a closing window.
• As we know, the luxury tax is always going to have a looming presence over the organization’s dealings. Ken Rosenthal reported on Friday that the Red Sox are expected to announce this deal as a six-year deal worth $160 million which would include his 2019 at the current salary, pushing the AAV of the deal down to $26.7. That would be good for the long-term implications of the deal, but it would push this year’s tax calculation up by over $10 million and certainly put them over the highest threshold. That seems like a strange move to make given their hesitance to make moves to improve the bullpen. Alex Speier later reported that the deal won’t have any effect on the 2019 luxury tax calculation. I’m going to hold off editing our payroll tracker until I get some clarification that this is actually how they plan on approaching this. If this is indeed the case, it makes their decision to stand pat in the bullpen this winter that much worse.
• I wonder how much effect, if any, this has on David Price. If Sale had left there’s a good chance Price would have been the number one in the rotation. I don’t think it’s fair to say he wouldn’t have been able to handle that, of course. He brushed off the postseason concerns last year and has been the number one in his rotations for the vast majority of his career. That said, it certainly has to feel better to have someone like Sale in the rotation with you.
• As you know if you follow the league beyond the Red Sox even a little, Sale is far from the only extension that has been signed lately. I don’t think we know enough about any individual player to give reasons why they might sign an extension like Sale’s a year away from free agency. In Sale’s case, this is the second time he’s signed a below-market extension to stay with his current team, and it’s fair to wonder if he just has never been someone who wants to deal with free agency. That being said, I think in general it is clear players are wary of the current free agent market and want to get a long-term deal while it’s readily available.