Since the popular narrative of 'They won't pay Mookie his money, but they gave stupid deals to Sale and Eovaldi' is rapidly becoming accepted wisdom among a majority of Sox fans, it’s worth exploring what an alternate history might have looked like.
First, we have to consider the issue of resetting the luxury tax. Some folks do believe that this is a red herring and that John Henry the billionaire should not let artificial limits like this one inhibit his spending. I believe that there is a valid argument that the Red Sox are best served by being a well-run organization, which can mean a. Not giving out $150 million deals to pitchers with injury concerns, while also b. Periodically get the payroll below the threshold (as the Yankees and Dodgers have successfully done) to remove taxes that effectively make every contract they sign more expensive, as well as restrictions that harm their ability to replenish talent through the draft and international player system.
So, in our alternate world, the Red Sox and Mookie’s agents hammered out a deal in early 2019. Let’s say they end up past the midpoint of the reported deals a little closer to Team Mookie’s side, signing a 12 year, $384 million contract. This pays Betts for luxury tax purposes $32 million per year.
In this new timeline, the Red Sox do not sign Nathan Eovaldi to a 4/$68 contract, nor do they extend Chris Sale in 2019. They blew past last season’s actual luxury tax threshold by $35 million, so foregoing Eovaldi doesn’t come close to resetting the tax last year, nor does, say, refusing to sign 2018 postseason hero Steve Pearce to his $6 million deal. There is no way the Sox realistically could have reset the tax in 2019, nor would it have been a good look to do so coming off a record year. How Dave Dombrowski replaced Eovaldi in the rotation can only be guessed at, of course - maybe finds the right guy to sign on a one or two-year make-good deal, but it’s hard to imagine that a 12-win gap with Oakland would have been made up.
(One can also imagine that word eventually gets out that ownership is tying DD’s hands in a desire to get under the cap, which probably evokes a minor sh*tshow in the Boston media about how those cheap owners are failing to take advantage of a championship window.)
Now it’s 2020. Having let an injured Chris Sale walk as well as a theoretical Eovaldi one-year replacement, the Sox drop below the $208 million luxury tax by around $12 million (assuming that no new long-term deals were agreed to beyond those we know of like the Bogaerts extension, etc.). The team now has three rotation spots to fill (including Rick Porcello), so maybe they do spend and wait until 2021 to reset. Now we’re at approximately $150 million compared to a $210 million tax threshold, again before any of those new salary commitments are added. At some point though, you are still looking at having to eventually fill three rotation spots and (after 2020) a full-time outfielder (replacing JBJ), plus presumably spending some money along the way to bring in reinforcements to the bullpen. If the team spends to fill those needs to stay in contention and push the resetting to 2022 or beyond, the player development system is hampered to a greater and greater extent, likely leading to a severe dropoff at some point absent ever higher levels of payroll (and CBT penalties paid).
I believe what this exercise shows is that there is not an easy solution - paying Mookie what he ‘deserves’ and keeping him in Boston for another decade (assuming that he’d agree to) would present major challenges in maximizing the window of championship contention during 2019-2021, assuming that John Henry does require his President/GM to reset the tax threshold at some point. It’s hard to see the Red Sox signing a true ace to head up the rotation to replace Sale or signing top relief pitchers to shore up the bullpen during this time period. In my opinion, I don’t think avoiding the Sale and Eovaldi deals mean that we’d have Mookie long-term *and* a no-doubt, top-tier contender right now - the die was largely cast by Dombrowski in building the 2016-18 team.
