Figured I'd put together a list of players who could make sense to offer extensions later this offseason (after the roster construction has been completed) or next offseason. Feel free to move this to a new thread if that makes sense. Would love to hear what other people think too.
In my opinion, the biggest factors to keep an eye out for are: the length/AAV of an extension, the timing of when it could occur (this offseason vs next), and prioritization (if a couple priority players get locked up first, other players may not make the cut due to the budget).
Kimbrel - FA after 2018
- Worthwhile offering an extension to Kimbrel this offseason since our roster is constructed to contend now and the window should still be open for a few more years. Would make even more money if he gets to free agency. Don't have any current RPs who seem likely to become closer material, unless Thornburg cleanly recovers from his surgery. Most of our other RPs are simply solid middle-relief, set-up type guys. Kimbrel is proven, consistent, and able to handle the pressure of Boston. Other elite RPs due to become a FA next offseason include Britton, Doolittle, J. Wilson, C. Allen, A. Miller, Familia, Herrera, Melancon, Ramos, Robertson. There definitely will be other options, but you'd still have to pay for them. Thus, Kimbrell wouldn't necessarily be a big priority, but it would be worth checking in to see if you can get him to sign a reasonable extension.
- I'd assume they would need to offer at least 3 years and > his current 13M salary due to inflation. Chapman and Jansen got 5 years, but they were slightly younger. Whereas Davis just got 3 + a vesting option, but he is older. Thus, if 4 years is what he would likely get as a reliever, an extension offer for 3 years + a vesting option could be a good starting point. A FA deal of 4 x 17.25M = 69M would give him the highest AAV for a RP. A reasonable extension offer might be something like 3 x 16.25M = 48.75M, with a 16.25M vesting option based on # of games finished.
Pomeranz - FA after 2018
- I don't think an extension would be likely for Pomeranz. The Sox would still have Sale, Price, Porcello, and Rodriguez, which is a solid foundation for the rotation. Pomeranz would likely want to get paid based on his 2016-2017 seasons, but those are his only 2 full years in the big leagues as a starter. He has had arm issues throughout his career and would be entering his 30s. The risk would probably be too high, especially since it would give the Sox 4 SPs with big contract (reducing flexibility in the event one or more of them regress). I would ride him out for what will hopefully be his 3rd consecutive solid season on a playoff contender and then re-evaluate needs in the offseason.
Sale - FA after 2019
- Sale would definitely be one of the priority extension candidates, but this could still wait til next offseason. He could certainly seek 30M/year, but I'd be afraid to sign him up for too long of a contract due to his skinny frame and violent, high-effort delivery. I fully expect Sale to remain an elite SP for the time being, but if and when that elbow breaks down, his career could take a quick turn. We have him signed up for ages 29-30, so the contract would be starting at age 31. Price, Scherzer, and Verlander got 7 years entering age 30, while Greinke got 6 years entering age 32.
6 (maybe 7) years at 30M+ as a FA would seem to make sense for Sale, so maybe an extension could get done for just 5 years and a bit less than 30M. If they offered 5 x 27M = 135M, they could override his 2018/2019 options worth 26M and just call it a 7 x 23M = 161M to lower the AAV in future years.
Bogaerts - FA after 2019
- I would not offer any extension this offseason since his career is still in the "what exactly is he?" stage. If Bogaerts remains close to what he was in 2017, then he might not be worth the considerable contract extension that Boras would likely demand. However, if he breaks out or at least returns at his 2016 level, he could be worth an extension next offseason. His position would be the most important factor because it's not easy to acquire good hitting and competent defensive shortstops. The Sox also don't really have anyone in the pipeline to replace him.
Betts - FA after 2020
- Betts would definitely be one of the priority extension candidates, but this could still wait til next offseason. Entering his age 25 season, Mookie seems like one of the rare players that would be worth signing to an 8-year extension. He is very athletic/fast, healthy, and a very good all-around player. It's pretty likely that he will remain at least a good player throughout the duration of the contract and he seems to be very focused on his long-term career. Even if he ended up regressing towards the end of the contract (age 30-32), he would profile well as a 4th OF type due to his defense/baserunning.
- Even if the Sox were comfortable going to 8 years, Betts may actually prefer only 6 or 7 so that he can hit FA at age 30-31. An AAV of 20M seems reasonable, especially since it would buy the Sox 3+ extra years on top of his 3 years of service time. There haven't been any comparable extensions across the league since Trout/Freeman signed back in 2014 and Posey signed back in 2013. Trout is the only ever pre-arb player to get an extension of > 20M AAV. The Sox reportedly offered 5 x 20M last year, but he declined. Thus, the biggest unknown is whether or not he declined because he wanted 6-8 years or if he wanted >20M. I'd certainly be willing to go to 7 x 20M = 140M.
Bradley - FA after 2020
- I would not offer any extension this offseason since his career is still in the "what exactly is he?" stage. If JBJ remains close to what he was in 2017, then he might not be worth the considerable contract extension that Boras would likely demand. However, if he breaks out or at least returns at his 2016 level, he could be worth an extension next offseason. However, I would consider this very unlikely due to his position. OFs like Betts and Benintendi can easily move around, so its not like the Sox will specifically need a CF if JBJ were to leave as a FA.
Rodriguez - FA after 2021
- I would not offer any extension this offseason since his career is still in the "what exactly is he?" stage. He seems like he will probably settle in as a middle of the rotation starter, but he could become a #2 type. Or he could continue to stall due to injury flare-ups. E-Rod would be a decent guy to monitor for next offseason in case he has a break-out season.
Benintendi - FA after 2022
- I would consider an extension this offseason. Benny has only played 1 full season in the big leagues, but has set himself a pretty high floor with a 20/20 season. With his athleticism, speed, and sweet swing, he seems to be the type of player that could be consistently good for years to come. If he puts up another solid season in 2018, I would consider an extension offer. The point of the offer would be to tack on an extra 1-2 years to his remaining 4 years of service time, while hopefully reducing the AAV in the long-run (especially if he later breaks out and becomes an all-star caliber player). Certainly worth monitoring.
- If the Sox wanted to approach Benintendi now, Adam Eaton's extension after 1 full season could be a reasonable framework. The purpose would be to guarantee the player money now, while gaining an extra year of service time and avoiding a potential big increase during arbitration if he becomes a star. Maybe something along the lines of 6 x 6.5M = 39M, which would actually be almost identical to Pedroia's first extension.