The only way you “reset” in a season is if your farm is ready to bring up multiple prospects and you have a season where you can deal off some assets. The Sox don’t have that kind of farm and I doubt the Sox are going to sell off anyone this season. There’s a reason why it’s called a cliff. If the Sox reset after 2019, you’re likely keeping one player from the Porcello, Sale, JDM, Bogaerts bunch. Subtracting 3 of those players will make your team middling. If DD tries to keep the band together and finds a way to keep 3 of those guys, 2020 will be a good season, but you won’t have the space to keep Betts or JBJ the following year. What we have seen teams try to do is avoid being middling. Picking in the 10-18 range in the draft does get you some talent, but does substantially decrease the talent obtained from the 1-10 spots. Add that to the added draft pool and IFA pool, and being a middling team kills the ability to add more talent later on in the draft while also killing your fan base. Now DD could reset then splurge after 2020, but what’ll that get you? You’ll be paying through the nose still for Pedroia and Price. You’ll presumably have Betts signed. Beni will start getting expensive as will ERod and you’ll be devoid of your most powerful bat and your best arm.
Add to that the fact that the Sox are in a division with a team on the upswing without the long term financial constraints and without the need to lock up a superstar within the next two seasons and you’re looking to turn the hammer into the nail in this division. I’d also like to add that Dombrowski has done this for a long time. He’s 63 and has a few titles under his belt now. Once the financial constraint blow this team apart, he’s leaving. He’s not going to rebuild at his age and with his resume. He’s already accomplished his mission.
My bet is DD rides out this season. If the Sox are as good as everyone thinks they are, he uses duct tape and bubble gum to keep as many of his big FAs as he can for 2020. After 2020, when even more difficult decisions come to play, he’ll likely saunter off into the sunset and allow his deputy to take over