Red Sox Head Towards a Crossroads with Mookie Betts

With president of baseball operations Dave Dombrowski fired and the team’s playoff odds heading into skim milk territory, the Red Sox have effectively thrown in the towel on 2019. Who will be charged with cleaning up the situation — a competitive roster that will nonetheless have significant holes to fill, a massive payroll that could limit their ability to do, a depleted farm system, and sky-high expectations nonetheless — remains to be seen. One thing is certain, however: at or near the top of the incoming executive’s to-do list will be figuring out how to handle Mookie Betts‘ pending free agency following the 2020 season. For as tempting as it may be to trade him before he walks away, the Red Sox could be making a serious mistake.

Betts, who will turn 27 on October 7, is in the midst of another fine season, if not one that measures up to last year’s high standards. Through Monday, he’s hitting .290/.388/.522 with 27 homers, 14 stolen bases, a 133 wRC+, and 6.1 WAR. Among American League players, his on-base percentage (fourth), WAR (fourth), and steals (10th) rank among the top 10, but for as impressive as that may be, it’s a marked contrast to 2018, when he led the AL in batting average (.346), slugging percentage (.640), and WAR (10.4) while placing second in on-base percentage (.438) and wRC+ (185), fourth in steals (30), and ninth in homers (32) en route to winning AL MVP honors in a landslide and helping the Red Sox to a championship. Not only was that 10.4 WAR higher than any player’s — even Mike Trout’s — since Barry Bonds’ 11.9 in 2004, but Betts posted that mark during his age-25 season, younger than any other 10-win player from the post-1960 expansion era save for Trout.

By that yardstick, Betts’ 2019 looks like something of a disappointment, though he has dug his way out of an early-season funk that saw him hit an unremarkable .243/.375/414 (108 wRC+) in May and June. Since July 1, he’s hit .329/.397/.616 for a 155 wRC+ and 3.3 WAR, the last of which is fifth in the majors in that span behind only Alex Bregman (3.8), Trout (3.7), Anthony Rendon (3.5), and Ketel Marte (3.4). Prorate that performance to his season total of plate appearances (670) and that’s 7.8 WAR with 18 games still to play — an MVP-caliber season in most years.

Betts is making $20 million this year, his second of arbitration eligibility. His salary is a record for a player in his second or even third year of eligibility; the only players with higher salaries prior to free agency were Super Twos who had a fourth year of eligibility (Nolan Arenado, Josh Donaldson, Bryce Harper). Unlike Boston’s other homegrown stars of recent vintage such as Dustin Pedroia and Xander Bogaerts, throughout his arbitration eligibility, the pint-sized right fielder has resisted signing a long-term extension. Following the 2017 season, Betts reportedly rebuffed an eight-year, $200 million offer by the Red Sox. In late March, when Trout’s 12-year, $426.5 million extension set records and significantly reduced the inventory of winter 2020-21 free agents, Betts said, “I don’t expect anything to happen until I’m a free agent,” though he did not completely dismiss the possibility of reaching an agreement with the Sox. In July, Betts attempted to clear any misconceptions that he’s unhappy in Boston, saying, “Just because you go to free agency doesn’t mean you don’t want to be somewhere. It’s just a part of the business.”

With playoff odds in the vicinity of 50% as the July 31 deadline approached, the Red Sox couldn’t have been expected to trade Betts, but with a 17-18 record since, winter is coming sooner than expected in New England, and it’s clear that hard choices will have to be made regarding the flawed roster Dombrowski’s successor inherits. As noted previously, the Red Sox are carrying the majors’ largest payroll whether measured by actual salaries ($236.17 million) or for Competitive Balance Tax purposes ($241.26 million). The latter figure is $35.26 million over the threshold, and as second-time offenders who have exceeded the threshold by more than $20 million, they’re subject to higher marginal rates and surtaxes; their tax bill for this year will exceed $12 million.

Even with Rick Porcello, Mitch Moreland, and Steve Pearce hitting free agency this fall, for tax purposes the team has about $134 million committed to just seven players, plus about another $17 million worth of minor league salaries and benefits according to our new RosterResource payroll pages — a count that includes J.D. Martinez, who can opt out of the final three years and $62.5 million of his deal, but also has an out after 2020, not that he’s getting any younger (he just turned 32). With next year’s tax threshold set at $208 million, and with a 50% marginal rate for overage based on being three-time offenders, the Sox don’t have a ton of room to pay their arbitration raises and retool their pitching staff and pay Betts, say, $27 million (assuming he surpasses Arenado’s record by $1 million). Not that owner John Henry, whose net worth is a reported $2.7 billion, can’t afford it, but the message sent by Dombrowski’s firing is an organizational expectation of some fiscal restraint, however artificial that construct may be.

That puts the new regime at an instant crossroads: retain Betts for 2020, and hope that they can outbid other teams once he hits free agency, or trade him this winter so as to generate a significantly greater return in prospects or younger players than by waiting until next July or letting him depart via free agency after the season. Neither route is for the faint of heart.

Barring an atypically down season from Betts — who has averaged 7.0 WAR over the past five seasons, this incomplete one included — re-signing him will likely require a commitment upwards of $300 million. Even under the relatively adverse conditions of this past winter, when teams did their best to freeze out free agents and highlight the flaws in their respective games and makeups, both Bryce Harper (who was coming off a subpar season) and Manny Machado (who spent October casting himself as the villain) reached that figure with long-term deals that began with their age-27 seasons. Betts’ next deal won’t begin until his age-28 season, but he will have outproduced both by a wide margin leading up to that point. Obviously, we don’t know what he’ll do yet in 2020, but he’s already banked 34.9 WAR since the start of 2015; even if with just 0.1 more this year and 5.0 next year, he’d reach 40 WAR for that period. By comparison, for the 2013-18 period (six seasons, paralleling Betts’ 2015-20) Machado produced 28.9 WAR and Harper 26.1. While teams have increasingly shown a resistance to paying free agents for past production, in this case, Betts’ recent past sets a significantly higher projection going forward despite his relative age difference.

As for the possibility of trading Betts a year before free agency, the notable examples of recent vintage all take a back seat when it comes to recent production:

Without getting bogged down in the details of each trade, I’ll present the deals here as taken from Baseball-Reference, mainly for scanning purposes:

• Goldschmidt: Traded by the Diamondbacks to the Cardinals for Andy Young, Carson Kelly, Luke Weaver, and a 2019 competitive balance round B pick.
• Heyward: Traded by the Braves with Jordan Walden to the Cardinals for Tyrell Jenkins and Shelby Miller.
• McCutchen: Traded by the Pirates with cash to the Giants for Kyle Crick, Bryan Reynolds and international bonus slot money.
• Samardzija: Traded by the A’s with Michael Ynoa to the White Sox for Chris Bassitt, Josh Phegley, Rangel Ravelo, and Marcus Semien.
• Upton: Traded by the Braves with Aaron Northcraft to the Padres for Max Fried, Dustin Peterson, Jace Peterson, and Mallex Smith.
• Céspedes: Traded by the Red Sox with Gabe Speier and Alex Wilson to the Tigers for Rick Porcello.

There are a lot of Remember Some Guys types of recent vintage, and just a few players who are particularly relevant in 2019, namely Fried, Kelly, Reynolds, Semien, and Weaver. Granted, a Betts deal might net a bigger name, but it’s not going to bring back the equivalent of, say, Yoán Moncada, whom the White Sox acquired when trading Chris Sale to the Red Sox thanks to the ace lefty’s three remaining years of club control at a rate well below the market.

Back to the table above, if he were traded, Betts would not be the youngest in this class, but he would be by far the most productive in the years immediately leading up to the deal. In fact, his WAR through age 26 is among the highest of the post-1992 expansion era, that while playing fewer games than any other player in the top nine:

If I had used age-25 seasons as a cutoff, Betts would still rank fifth at 30.6 (in just 644 games), and Heyward would crack the leaderboard at number 14 with 25.1 WAR (in 838 games). All of which is to say that this is a very special player, one who’s laying down tracks to Cooperstown — he’s approaching the peak standard for right fielders in terms of bWAR (41.4 vs. 42.1) before the end of his sixth season, and should surpass it in his seventh — and one for whom there aren’t any true parallels for such trades.

Here it’s worth noting that in the winter of 2017-18, the Orioles explored trading Machado and likewise for the Blue Jays with Donaldson. Both were coming off of comparatively subpar years; Machado was worth just 2.4 WAR in his age-25 season after totaling 12.9 WAR over the previous two years, while Donaldson was worth 5.1 WAR in just 113 games in his age-31 season (having missed six weeks due to a right calf strain) compared to 16.3 over his previous two seasons. Whether out of concern that their most recent seasons were the start of downturns or signs of future health woes, the gap between their respective teams’ asking prices and the offers they received obviously wasn’t enough to consummate deals in either case, but in both, the teams received even less in return when trading them before the deadlines (Machado to the Dodgers on July 31, Donaldson to the Indians on August 31).

In the end, there’s a reason it’s hard to find a recent parallel for Betts’ situation: great young players like him generally don’t get traded, both because it’s difficult to generate significant value in return and because, well, giving up a generational talent isn’t a good idea. The Red Sox have put themselves in a difficult position given their current payroll situation, and while the new regime should explore his market this winter in case they’re bowled over, trading him simply for the sake of trading him would be cutting off their collective noses to spite their faces. Henry and whoever it is that succeeds Dombrowski need to figure out a way to play out the 2020 season and keep Betts in Boston.