The Red Sox have made massive strides with their rotation thus far this winter, bringing their total of legitimate MLB players to five. Despite it being consisted of mainly mid rotation types, it is not at all impossible that the team heads into the season without making any more additions. With that being said, in a more ideal world they would add a legitimate front-of-the-rotation piece to add more talent and consistency to the unit. Of course, that’s much easier said than done, and there aren't a ton of options remaining on the market. I’ve already laid out my case for wanting James Shields, but even I can acknowledge there is risk involved. The other option many have laid out is playing out the 2015 season and reevaluating the situation next offseason when a number of studs are set to hit the open market. Now, Marc already addressed the problem with assuming they’d be willing to open their wallets after failing to land Jon Lester, and it’s an important point to consider. That’s not the only problem, though. Just assuming that all of them will make it to free agency is a dangerous game, as most of them have a decent chance of being locked up before they get to that point.
We start with a guy who has been linked to Boston already in trade talks. With Washington finding themselves with Zimmermann, Doug Fister, Ian Desmond and Denard Span all hitting free agency next winter, the assumption is that they will not be able to re-sign everyone, and thus will look to deal from their starting pitching depth to help their future. Given their depth at the position and the price tag he'll command, Zimmermann is the least likely to be re-signed. However, the problem comes with him possibly being traded. With the asking price from Washington, the returning team would be very motivated to work out an extension. Teams would probably need an assurance from his agent that he’d be willing to negotiate before pulling the trigger. So, if he stays in Washington through the winter, I’d expect him to be available to sign next offseason, but those odds dramatically decrease if he is dealt in the coming weeks.
The Reds are in a strange position where they have sold off a few key pieces of their rotation, but still are looking to contend. It’s noteworthy that they have not dealt Cueto, though. It’s certainly possible they only want him for the first half since they are hosting the All Star Game this year, but it appears more likely Cincinnati is looking to lock up their ace. Cueto is one of the elite arms in the game, and they’ve expressed time and time again they’d like to keep him around. Sure, they’re not a big payroll team, but they have some money coming off their payroll next year, and Jay Bruce’s deal ends the year after that. It would be a squeeze, but given their apparent motivation there is at least a 50/50 chance he is locked up before he can hit the open market.
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Price is another strange case because of the unpredictable nature of the Tigers. We always tend to assume they are out of money, and then they take on another huge contract. What this really comes down to for me is whether or not they re-sign Max Scherzer. As of right now, Anibal Sanchez is their best bet at a long-term ace, with Justin Verlander showing signs of decline. If Scherzer signs elsewhere, it wouldn’t surprise me in the least if extension talks between the two sides heat up. Of course, Price would have to agree to forego his right to hit free agency, but if there’s one owner who I could see showing him enough money to do so, it’d be Mike Illitch. There is also the possibility of him being dealt. As it was with Zimmermann, the presumption would be that the acquiring team would be looking for a long-term contract upon trading for Price.
Technically, it is no guarantee that Greinke will even be eligible for free agency next winter. He has an opt-out in his contract next winter, and he could certainly decline it and finish out his deal with Los Angeles. Of course, with the way he’s pitched since joining the Dodgers, it’s extremely unlikely that will happen unless he gets injured or completely falls off a cliff. To this point, LA hasn’t made an effort to work out an extension, and Greinke has commented multiple times on how fascinated he is with the free agent process. The price tag will be huge, but I would bet on him becoming a free agent a year from now.
In the Zimmermann section, I already commented on Washington possibly swinging a big trade this offseason. Well, Fister is a possibility to be dealt as well. In fact, I’ve already argued he’d be a nice target for Boston. The difference here is that he will not carry the same price tag as Zimmermann, making it more likely that the Nationals would want to keep him around for the next few years while their window is open. They would certainly have the money for it with all of the cash coming off the books this winter. To this point, there has been no progress towards an extension, but I’d look for that change as spring training gets closer.
Iwakuma is another guy who has been on Boston’s trade radar this winter, though any possibility of that likely went out the window when Yoenis Cespedes was dealt for Rick Porcello. However, with just one year remaining on his deal, his name could be attached to the Red Sox once more. The problem, though, is that he and Seattle seem to have a very good relationship. The team seems satisfied with their lethal one-two punch atop their rotation, and have shown a clear willingness to spend money to remain competitive. With that being said, there have been no extension talks to this point, and the longer they put it off, the more likely it becomes that he looks elsewhere for a big payday. Still, the gut feeling here is that his relationship with the city is strong enough that something comes together at some point.
Jeff Samardzija/Mat Latos
I am grouping these two together because neither is very likely to sign an extension. Latos was just traded to Miami, and I don’t think I need to explain why they aren’t likely to make a big commitment to Latos. This is especially true if they are serious about locking up guys like Jose Fernandez and/or Christian Yelich. Samardzija was just dealt to the White Sox, and while they don’t have the same reputation as the Marlins, they have a lot of money on the books in the future. On top of this, Chris Sale and Jose Quintana are already an attractive duo to build their rotation around. Of everyone on this list, these two are the surest bets to be available next winter.
The point I want to make here is that it’s a dangerous game holding steady right now with an eye towards next offseason. A lot can change between now and then, both with the Red Sox and the rest of the league. Of course there is a lot of speculation involved, but by my estimation, there are really only two sure-things (or as close as you can get to a sure-thing) to hit the market, and they’re probably the two worst pitchers on the list. So while the projected free agent class next winter has the potential to be stacked, it’s much more likely it ends up like most other classes, with one or two front-line starters hitting the open market with the rest getting locked up before they get to this point. Between Marc’s point about their chances of spending big on a SP and the risk of most of these pitchers getting an extension, the thought of waiting until next winter to address the top of the rotation is a scary proposition.