Crossroads: Boston and Bogaerts

As the play clock winds down before the craziest day of the year baseball wise, the Boston Red Sox seem to be approaching a significant crossroads as an organization which I don't think is getting enough attention. 29 year old star shortstop Xander Bogaerts has an opt-out after the season, and is not only the veteran of the team, now in his 9th season with the club, he's also without question one of the two best players on the squad, alongside 3B Rafael Devers.

The shape of the organization bears the scars of the era preceding this one, the period between 2015 and 2019 when Dave Dombrowski was steering the ship. As many fans know, Dombrowski is a seasoned front office decision maker, and his hallmark approach is to pull as much future value out of an organization's system and convert it into value in the very short term. This has the effect of obviously consolidating the overall value in the system into a shorter window of contention, allows the team to fill holes on the Major League roster that may otherwise go unfilled, or left to generate replacement level value. It also strips the likelihood of the organization's system to graduate quality major leaguers in the medium to long term, in baseball terms I’m talking roughly 3-6 years out.

He's done this largely via gutting farm systems of talent across levels, in Miami (then Florida), Detroit, and most recently Boston. These trades have often worked out, as he was able to bring enough talent to the Marlins to win a title in 1997 (sadly he'd have to dismantle the team only months later to reduce liabilities on the balance sheet before the owners sought to sell the team) as well as winning the pennant with Detroit in '06 and '12, though they lose in the World Series on each occasion.

If you'd like to get an idea of Dombrowski's transactional philosophy, this article by Scott Lauber at ESPN a few years ago is a good introduction.

Dombrowski would leave Boston in September of 2019, ending a ~5 year stint that can only be described as a complete success given what it feels like his mandate must have been - something along the lines of "aim to win 95+ games a year even if it means utterly disregarding how we'll compete next year, let alone three years into the future".

The Sox finished last in the East in 2014, as well as in 2015, but the team was reformatted over that span of time and won the AL East in three consecutive years from 2016-2018, with the '18 season of course ending with champagne showers and a nice new piece of jewelry for everyone involved. Then 2019 saw the team slip, finishing in 3rd place and missing the playoffs. While they didn't participate in the postseason, it's tough to say that the team was bad, or even that they were not built to win, but despite strong performances by Mookie Betts, Bogaerts, Devers, and J.D Martinez at the plate, holes in other areas sapped a lot of potential from the season.

Catcher, 1B, 2B, and LF saw below average (not replacement level) performance, and the weight of those relative weak points kept the team from having what could, and probably should've been a top offense in the league. The organization had moved a ton of potential depth pieces in exchange for players like Chris Sale, Craig Kimbrel, and others, and one way or another, Dombrowski was gone, (he'd shortly afterwards be hired on as President of Baseball Ops. in Philly) the page turning to the next chapter in organizational leadership at Fenway.

Today, the Sox are in their third season with Chaim Bloom running the show upstairs, and on the field the team is undoubtedly led performance-wise by Xander Bogaerts, who has been with the organization since signing out of Aruba in 2009 as a 16 year old. He hit 45% above average in rookie ball as a 17 year old the next year, lit up AAA as a 20 year old in 2013, and went on to play a not insignificant role in the playoff run that led to a ring with 34 PA's in 12 postseason games that year. Since then he’s played 8 full seasons of phenomenal baseball, ranging from above average to fringe MVP candidate level of play.

600 words in and we're finally at the meat of the article!

The whole reason I felt compelled to put this together is that Mr. Bogaerts has the ability to opt out at the end of this '22 season, or to forgo that option and continue on his current deal for three more years earning 20M per year. Bogaerts also has a full no trade clause in his current deal, meaning the Sox can only deal him if he agrees to it. You may read that and think man, why include the opt-out or the NTC in the first place, why get yourself into this situation as an organization? The best answer I can give is that the combination of the clause and opt-out are likely the two most important reasons why he agreed to a 6 year $120M extension in the first place three years ago.

You can think of the second half of his deal, the piece after the opt-out, as a sort of $60M insurance policy on his own performance declining, whether injury related or organic, at any point in the past three years. I think it’s pretty clear that while he’s probably glad he’s had that policy in his back pocket, that hypothetical decline scenario has not transpired, and today Bogaerts is one of the premier talents in the league. A 4 time All Star at one of the most important positions defensively, he adds value in every way it can be compiled. He’s a productive hitter, fielder, baserunner, and he’s widely regarded as a positive clubhouse presence.

This whole situation puts the team in a tight spot, because they have recently gone through a downturn that has seen their playoff odds plummet, according to Fangraphs playoff odds calculations, as you can see here:

I think the best way to understand this is through comparisons of two projections at three points in time.

On June 26th, their odds to make the playoffs were ~80%, with a projected win total of 88. On July 10th, those odds had slipped a bit to 75%, with wins projected at 87. Not at all a weird fluctuation over the course of a season, however as I’m writing this on July 25th, ~two weeks later, those playoff odds are down below 27%, and the team is projected to win 82 games, a lukewarm outlook at best.

In the AL Central an 82 win projection doesn’t crater your odds of making an October run, but in the East every team is competent and currently competitive. The “bad team” in the division, the Baltimore Orioles, who in theory should be at the bottom of a trough in the middle of a full on reboot of the system, firmly in a rebuilding phase that comes before the proverbial window opens, instead find themselves rapidly rising in competitive ability, and are now only one game behind Boston (though they are projected to slide a bit and finish with 75 wins).

Summarized, the divisional competition is about as fierce as you ever see, and they have had a serious string of underperformance punctuated by poor luck. I haven’t even touched on Devers’ hamstring or Sales’ disintegrated pinky finger (that was gnarly).

I believe, and have to imagine that Bloom and his team believe, that the optimal outcome from a team building perspective would be to retain a player of Bogaerts caliber, at a reasonable AAV, for a period of time that minimizes the risk of it becoming an albatross down the line. That’s not a brilliant original thought of mine or anything, but I think it’s safe to say that if he is open to an extension at a reasonable rate and duration, that the team would want to keep a known commodity at a crucial position around. This was of course also true for his former teammate and franchise great Mookie Betts, who the team was not afraid of dealing prior to his potential departure via free agency. But we all witnessed the series of events surrounding Betts departure westward, and it feels naïve to assume that Bloom will be more open to spending on a market rate extension for his shortstop than he was for the guy who was at the time the consensus 2nd best overall player in baseball behind only Mike Trout.

This isn’t even getting into the perspective of ownership, who surely view Bogaerts as the player that drives viewership more than anyone else. I don’t have my own model or method of measuring this, but it “feels” like the vast majority of value the Red Sox players contribute as an entertainment product is likely concentrated between Bogaerts, Devers, J.D. Martinez, Eovaldi, and Chris Sale. It’s also a tossup between Bogaerts and Devers for which current player has the best chance (really any chance at all) of eventual enshrinement in Cooperstown while spending their career in Boston, or of getting their number above the grandstands behind Pesky’s Pole. I suppose Sale and Martinez have a shot, but they’ll need to age like Scherzer and Beltre to do so, a tall order for anyone.

This has a legitimate, though definitely uncertain to me, value in dollars to ownership, and it is definitely an aspect of the conversation when teams look to move a player. I have my suspicions there’s a chance that it’s not considered strongly enough (I’ll probably end up writing more on this at some point), but as evidenced by the willingness of teams to move top players, that value is clearly not often seen as worth a contract that the team defines as too risky, representing too great a concentration of their available resources, or both.

I think the reality is that we have to assume Boston will explore the option of dealing Bogaerts instead of letting him walk in Free Agency. While they would appear to be able to tag him with a qualifying offer to recoup an early round pick upon his signing elsewhere, that avenue to a mild return upon his leaving the team could cease to exist at any moment, as the league is currently negotiating with the Players Association on an International Draft, which the recently signed CBA stipulates would eliminate the qualifying offer system in favor of a new method of providing teams with compensation for departing free agents. While that could very well be comparable to the current QO, it's also an unknown, and the negotiations could just as well remove a lot of the value the current system would deliver Boston upon his potential departure.

From a purely value perspective for the player and his agent Scotty Boras, the decision is a simple one. He can without question get dramatically more than 3 years and 60M on the open market, in fact I think somewhere in the range of 2-3x the years for 3-4x the money is probably most likely. At worst, he could probably receive an offer similar to his teammate Trevor Story, who inked a 6 year, 140M contract with Boston just last year.

Bogaerts could alternatively pursue a high AAV short term deal like the one Carlos Correa received from Minnesota this past off-season. He already has the comfort and security that has come with his ~$70M career earnings, and he played it safe last time. It’s not tough to envision a scenario where he chooses to maximize his potential earnings now that he has secured generational wealth through his current contract.

A Correa-shaped deal would allow him to maximize short-term earnings, while providing the opportunity to capitalize on a stellar year if he were to happen to put up 7 WAR or something in '23 or '24. The list of teams that would consider him at $90M/3 years or $130M/4 years would surely include suitors with deep pockets, and/or those who are attempting to compete in the moment, such as the Dodgers, Angels, Mets, Cubs, Yankees, Orioles, Cardinals, Brewers, and Padres (there's no reason you couldn't have Tatis, Machado and X share the left side of the infield while Tatis moonlights in LF, and all three rotate through the DH spot).

Hell if the rumors of the Nationals wanting big league players in return for Soto are true (seems like a bad idea to me), who's to say they don't flip him for 3 passable starting bats and then add Bogaerts and someone like Dansby Swanson to form a stellar left side of the diamond. They could even bring Trea Turner back to DC and stick him in center to add another impact player at far less of a guarantee than what Soto will command. If they want to ignore their significant lack of a minor league pipeline and simply aim to reload the roster, adding Bogaerts to the Soto return would not be a bad move at all.

My point is that contending teams are going to be open to paying Bogaerts substantially more than he will make by forgoing his opt out, even over the same time period. He knows this, Boston knows this, and teams that may want to acquire him know this.

If you're Boston, I have to imagine you're operating under the assumption that you either extend Bogaerts "now" by modifying his current deal, or, if you're unable to reach an agreement with him in the moment, that you attempt to trade him in the next two weeks to a team that both would want to sign him with the move being contingent upon Bogaerts signing that extension as the ink dries on the trade itself. This would allow a team that wants him to get him without the issue of courting him on the free market, and would offer Boston a chance to reduce the risk of the return for his departure returning less than today's QO would.

Due to the fact that he's not already been extended today, July 25th, I have to imagine that these conversations are taking place between Boras and Bloom's department, as well as between Bloom and the front offices of other teams who see him as fitting their timeline. The one wrinkle that the Red Sox cannot control, however, is that all of this is dependent on Bogaerts waiving his full no trade clause, which means if there’s a team that wants him, with an offer Bloom deems appropriate, that’s all null if Bogaerts wouldn’t want to play there.

An offer here has to, in my mind, start at a player who Bloom sees as having more value than a QO pick, although it’s more complicated than that, because if an extension is a contingency within the deal, which I don’t see why it wouldn’t be, you’d think some teams would be willing to offer even more in return. The type of extension he prefers certainly affects this calculus, because if he’s seeking a Correa deal, the return simply can’t be the same as if he wants a “rest of my career” deal. Either way, the option to add him to your team should be appealing to a wide swath of the league, and I think we’ll hear rumors about this in the coming days.

Lastly, I think in a way the clause doesn’t necessarily make a trade less likely. He’s going to want more than 3 years and 60M, he presumably would rather be playing baseball this October, and if he has the chance to lock up the type of deal he wants this week, with a team he’d like to go to anyway, why linger in Boston in lame duck status while the team wins 75-85 games, with odds consistently growing you miss the playoffs, with the risk of injury in the next 2-3 months negatively impacting his earning power? The clause gives Boras and his client power, it gives them control, and it also gives them leverage in the negotiation with Boston at the moment (which I think may be making it less likely he is extended before the deadline).

I’ll try to write up a piece tomorrow with more specifics about who I think might target him in this deal, and what they might be willing to give up to add him, but I really feel like this is a scenario that the mainstream baseball media is missing, and it’s going to have huge ramifications on the rest of Boston’s roster. Devers will be a free agent at the end of the ‘23 season, and it doesn’t seem farfetched to think that he’s less likely to re-up with the Sox if they trade his partner in crime, or let him walk in free agency. Like the main character in this article, Chris Sale can also opt-out this offseason, and many others on the roster, including J.D. Martinez and Nathan Eovaldi will be leaving at the end of the season as well. I’m looking forward to the insight we get into Chaim Bloom’s series of decisions, and feel like along with the Betts decision, the end of this season and the handling of Bogaerts, as well as the others mentioned in this piece will come to define his tenure in Boston one way or the other.