Let the Crazy Begin

Xander opts out, Edwin Diaz re-signs in New York: the off-season gets going!

Photo by Will Myers on Unsplash

This off-season should be an active one for the Red Sox. By default they’re going to either commit to their All Star core or they’ll have to create a new one. They’re going to have to rebuild their pitching staff from the top down, both in the rotation and the bullpen. They could do even more, including overhauling the outfield and rebuilding the catching position. It’s a lot. And it’s happening fast.

Let’s talk about it.

The first order of business is to extend Xander Bogaerts’ deal. So Mission Failed on that one. Bogaerts officially opted out of his contract and became a free agent on Monday morning. The Red Sox front office talked all season long about how they wanted to keep Bogaerts in Boston, but at least up to now, they’ve failed in that pursuit. It could still happen, of course, but now it’s going to happen with an assist from the market.

That might not be a bad thing, assuming the goal is to keep Xander in Boston long term. There are, after all, a number of very good free agent shortstops on the market simultaneously, so scarcity won’t be on Bogaerts’ side. It’s entirely possible that the market for Bogaerts won’t develop to his liking, and the Red Sox will be able to use that to hammer out a long term deal with the team’s de facto captain on or at least closer to financial terms they’re more comfortable with.

It’s also entirely possible that Bogaerts and the Sox have some sort of understanding, that they’re going to let the market dictate the parameters of his next deal, and once they gather a mutual understanding of those parameters, they can get down to negotiating specifics.

That is all possible. But I suspect it’s more likely that the Red Sox have a number. What I mean by that is the Red Sox have drawn themselves a line for Bogaerts’ next contract that they won’t go past. That’s not a bad idea business-wise, but it’s not the kind of thing that is effective in getting free agent deals done.

Having a number is often dictating by the the market, but not the current market, the past market. If the market is slower for a player, then that can work, but for star shortstops, that’s not often how it plays out. And as I wrote previously, if the goal is to sign the player, often that will mean extending beyond what is comfortable. If the team isn’t willing to do that, then that means the player is going to have to go elsewhere, and I strongly suspect that will be the case here.

There’s an argument to be made that that’s actually the best case scenario for the Red Sox’ future. I’m not making that argument, but I will point out a few things here. The track record for 30+ year old shortstops is not a good one. Shortstop is decidedly a young man’s position, and Bogaerts just turned 30, crossing that most holy of thresholds from young to, well, not young anymore, on October 1.

Further, if you examine Bogaerts’ season, you can find a lot that might be concerning if you had him locked up long term. The power dried up, for one thing. That doesn’t mean it’s gone forever, but 15 homers from a guy who has averaged 25 a season since he was 23 isn’t, as they say, what you want. But it’s not just that a few more balls hit the top of the wall rather than going over. Bogaerts’ Hard Hit Percentage, his Average Exit Velo, and even his sprint speed were all down in 2022.

I wrote about this before, but it’s worth saying again: so much of Bogaerts’ value in 2022 came from two things: 1) his improved defense, and 2) getting a lot of singles on ground balls. Bogaerts hit .341 on grounders in 2022, a full 50+ points above his career average. Given his declining foot speed and decreasing Hard Hit Percentage that’s not likely to happen again in 2023, and it’s certainly not something you’d want to lock yourself into depending on for the long term.

So there are worrying signs on the field for Bogaerts. To maintain his value he’s got to keep his defense up, which is difficult for any shortstop playing into his 30s, let alone one of Bogaerts’ defensive past. He’s got to hit for more power, and he’s got to make better contact. But here’s the thing: he could do those things! He could! It’s not like one season is inescapable destiny. It isn’t. Great players have down seasons sometimes, and batting average and WAR aside, 2022 was a down season for Bogaerts, at least when it comes to his metrics and the standards he’s set for himself during his stellar career.

It’s hard to tell right now if the Red Sox believe in Bogaerts’ ability into his 30s. They’ve talked about all the things he brings to the team off the field and in the clubhouse, but you don’t get $250+ million because you’re a team leader. I know that’s a fun media storyline, and it’s true teams might pay a bit on top for that kind of thing, but that’s not why you sign someone long term. You sign someone long term because you believe they can help you win baseball games for a long time. It’s not clear right now that the Red Sox believe Bogaerts will do that, at least not in relation to the money and time commitment he’s asking for.

Many people have said that the second order of business for the Red Sox this off-season (and I might be one of those people) is to extend the contract of Rafael Devers. Reports have come out that the Red Sox have already started the process of doing that. But so far they’ve not had success. There are a few issues here worth discussing, and the first is timing. It has been speculated that the Red Sox will wait until the end of the off-season and maybe until Spring Training to extend Devers’ contract. The problem with that is that if they can’t do it, they’re left with a player playing out the final season of his deal. Teams typically don’t like to do that. That was the issue with Mookie Betts.

While the Red Sox have publicly said they don’t intend to trade Devers, I have to wonder what they’ll do if they hit a contractual impasse. There are too many holes on the roster and Devers is too valuable a player, even on a one year deal, to let walk for a mid-round draft pick. But if they wait until the spring, rosters will be set and making a deal for Devers will be much more difficult. With that in mind, I think there’s a push to extend Devers coming soon (if it hasn’t already happened) and if it fails, then exploring a trade seems likely.

Again, I won’t make the argument here, but one could be made that says spending $300 million or whatever it would take to lock up Devers long term isn’t wise. Devers, like Bogaerts, had a good defensive season, but his poor defensive past isn’t so far behind him as to entirely discount it. There’s a case to be made that his home in the near future isn’t at third base, and that means either a move to first base or DH, both of which would hurt his value. First basemen don’t typically make nearly as much as third basemen on the market, something we saw last season as both Freddie Freeman and Matt Olson signed long term deals with average annual values of $24.7 million and $21 million, respectively.

If reports are to be believed, Devers is looking for significantly more than that, but if his long term home isn’t third base, that would be a huge overpay. Which, fine, whatever, who cares, except duh, of course the Red Sox care. We can say it’s dumb and they’re the Red Sox and they should act like it with their star players as much as we want, but the reality is this is how they’re going to conduct business. If they spend $300 million Devers, they’re less likely to add in other areas.

All of which is to say much of this could happen quickly. Clearly the Red Sox already have an idea of what Bogaerts wants and clearly they’re not comfortable paying it, or they’d already have his signature on a new contract. Similarly so with Devers. If Bogaerts isn’t coming back, they’re going to need someone to play shortstop. If Devers is on the trading block, they’re going to need someone to play third base.

If both of those things come to pass, it’ll be interesting to see which way the Red Sox go. They could continue to build internally, sign a stop-gap shortstop, trade Devers for a top prospect or two, and make a(nother) long term plan. If they have the right front office in place that might be a winning strategy, ultimately. But I suspect ownership won’t allow the Bloom administration that amount of leeway.

Beyond figuring all this out, and the pressure on Bloom to win right now which could result in some more Dombrowski-esque deals, there’s the entire pitching staff which needs an overhaul. The first thing is to decide on issuing qualifying offers. There are three starting pitchers who the Red Sox will need to decide the contractual status of. Both Michael Wacha and Nathan Eovaldi are candidates for the qualifying offer, which this year will be just south of $20 million. Much has been said about the Red Sox issuing qualifying offers to both, but that’s a large expenditure ($40 million) if they accept, and if they turn it down, because of Boston’s situation relative to the luxury tax threshold, the return is something around a 4th round pick. I don’t think that math works.

I also don’t think Wacha is worth that money regardless (we can get into that later), and while both he and Eovaldi will get multi-season deals, they very likely won’t be at $20 million a season. Unless the Red Sox know for a fact the pitcher they give it to will turn it down, I don’t think they can chance it.

The other pitcher why they need to make a choice on is James Paxton. Paxton’s deal was for one year at $6 million with a team option for two more years at a total of $26 million. As Paxton didn’t throw a pitch in 2022, there’s no way the Red Sox can commit $13 million to him for two more seasons. That option has to be declined, and I’m sure the Red Sox will do that. Paxton has a player option for 2023 at $4 million, and I have no idea if he’ll pick it up or not, but $4 million for James Paxton’s 2023 season is fine. Whatever.

Beyond all that, the Mets have spent $102 million to keep their closer for the next five years, so any fantasies you might have harbored over Timmy Trumpet playing at Fenway Park next year can be tossed in the garbage.

Thanks for reading.