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These Red Sox players are extension candidates this winter

Some money may be spent on returning players this winter

MLB: Boston Red Sox at Cincinnati Reds David Kohl-USA TODAY Sports

On Wednesday, we touched on some reports that stated the possibility of Dave Dombrowski sticking to second-tier players on the market this winter and instead focusing his big expenditures towards extending some key players already with the Red Sox. As I state in the linked post, I’m not really sure I buy that and am still pretty convinced at least one big splash will be made over the next couple of months to improve the lineup. It’s just Dombrowski’s nature. That being said, the idea that an extension or two could come this winter makes a ton of sense, as Boston has plenty of players who are candidates for a longer-term deal right now. Let’s take a look at each of them, in order of most-to-least likely to be a priority this winter.

Mookie Betts

There is no doubt as to who would be the top priority for the Red Sox to extend if they could do so for any player they wanted. Betts is already one of the game’s premiere players, and 2017 proved that his floor is exceptionally high given his elite baserunning and defense. When you add in his raw offensive talent, the fact that he only just turned 25 and the fact that he’s the most marketable player on the team, you have a guy that you could envision being in Boston for the next decade. Of course, these kind of extensions are a two-way road, and Betts to this point has not given any indication he’d be interested in a long-term deal. He is just now entering his first year of arbitration and won’t be eligible to hit free agency until after the 2020 season, so he has time to play year-to-year for now and not take a below-market deal just for long-term safety. That being said, the Red Sox would be silly to not at least check in every so often to see if he’s any more open minded. Betts should be the face of this team for the foreseeable future. We’ll all feel better the sooner he is locked up long-term, even if we can’t blame him for wanting to wait.

Chris Sale

Although Betts has been with the organization for years and has long been viewed as a future centerpiece of this organization, Sale has only been here for one year. That being said, it became clear in 2017 that he is the front-line starter this team has been looking for since Jon Lester left, even if Sale is considerably better than Lester. The lefty, who just finished second in the Cy Young voting, combines just about everything we want from an ace. He is wickedly talented, racks up strikeouts to an absurd degree, and has a mean demeanor on the mound while he’s throwing. The only thing that’s missing is keeping it up deep into the year, but the Red Sox are working on that. In the meantime, his team-friendly deal he signed in Chicago has just two more years left, and now is the time the Red Sox could start looking to keep Sale around long-term. This extension would be a bit different than Betts’ for a few reasons. For one, the fact that Sale is a pitcher makes him much more risky. Plus, he is about to start his age-29 season and would be 30 by the time an extension began. Those things would suggest he’d be cheaper. However, he’s also a more established star in this league and has already signed a team-friendly extension once. It’s always hard to say exactly what Sale is thinking, but he’d have every right to say he wants something close to market-value if he’s going to sign another extension. I don’t expect to hear much about these particular talks until at least spring training.

Drew Pomeranz

Pomeranz is one of two big-time pitchers on this roster who are set to hit free agency next year. He is still something of a confusing pitcher, though he was undeniably excellent for the vast majority of 2017. Even later in the year, when his velocity dipped to a dramatic degree, he was still turning out effective outings. He made a bad first impression in Boston, but over the last two years he’s proven he’s a very good major-league starter. That being said, there is still some injury risk here and that’s always the scariest type of player to sign to an extension. I wouldn’t be surprised if the two sides talk this winter and into the spring, but there’s a wide range of possibilities for Pomeranz and he may want to bet on himself. If he can make it through a full year in 2018 and pitch like he did a year ago, he’s going to get a major payday on the open market next winter. The issue for the Red Sox is that they don’t have an obvious replacement unless Eduardo Rodriguez starts to show some consistency.

Craig Kimbrel

Kimbrel is the other star pitcher set to hit free agency after the 2018 season, and if you want to argue that he should be above Pomeranz I won’t argue back much. I’ve switched the two back and forth about 50 times. Kimbrel is, without a doubt, one of the very best relievers in all of baseball, and while there is always some apprehension around long-term deals to relievers I am of the belief that it’s different when you’re talking about the top tier. Kimbrel is on a Hall of Fame track, and I wouldn’t be worried about locking that up for four more years. That being said, the Red Sox may not want to tie money down in the bullpen, and Kimbrel may want to test an open market that has been more and more friendly to relievers in recent years. Letting him walk would be a big risk for the Red Sox, who could have replacements in place with Carson Smith and Tyler Thornburg, but we haven’t seen nearly enough to say that for sure. At the very least, I would expect these two sides to keep in touch all year long.

MLB: Pittsburgh Pirates at Boston Red Sox Greg M. Cooper-USA TODAY Sports

Xander Bogaerts

Here, we have a player who has become quite divisive over the last couple of years. It’s true that Bogaerts has not turned into the player most of us expected him to be, and it’s also true that his 2017 was disappointing. If you believe that’s his true talent level, you don’t want to extend him. If you believe he’s only going to go up from here, you do want to extend him at his current value and potentially get a steal for years to come. Of course, Bogaerts really has no incentive to negotiate an extension at this point with his value at its lowest. He has two more years before he hits free agency, and I wouldn’t expect extension talks to begin until at least next winter.

Jackie Bradley Jr.

One could certainly argue that, in a vacuum, Bradley is the more valuable player than Bogaerts at this point in should be the higher priority. We’re not in a vacuum, though. For one thing, Bradley has an extra year of control over Bogaerts, so that sense of urgency isn’t quite to the same extend. Plus, the Red Sox have two other outstanding young outfielders who could slide into center field. Bradley is a fun player with a ton of upside and I’m sure the Red Sox would love to have him long-term, but it’s not an absolute necessity at this point.

Christian Vazquez

Vazquez is under control through 2020 just like Betts and Bradley, and he’s coming off a year that suggests he could be an everyday catcher moving forward. That’s not something I thought I’d ever say, but he was legitimately impressive at the plate. That being said, it’s not clear how sustainable that is, and it would probably be smarter for the Red Sox to play this out for another year or two before entering extension talks.

Andrew Benintendi and Rafael Devers

These two rookies are arguably the second and third most exciting members of the lineup, but both are still pre-arbitration players and under control for a long time. An extension this early would be cool, but it’s not a priority at this point.