If the Sox rebuild, there’s zero chance it’s a one year thing. When you dealt Lester, Miller and Lackey, you had the #1 farm system in baseball. You drafted Chavis in 2014, the following winter you signed Moncada, and the following draft, with a really high draft pick, you got Beni. You had Devers, Kopech, Betts, Vasquez, etc all in the minors. You had just graduated Bogey. Timing is everything. You dealt Lester in 2014, then sucked again in 2015 while trying to decide if the rebuild had worked. That is what led to the Dombrowski era.
Dombrowski has leveled your farm. Like salted earth and flames. So bad that outside of a single prospect (Casas), nobody wanted your prospects for pen help. DD said he was “good with what we have” but that really isn’t true. Teams with pen upgrades weren’t interested in s*** prospects. He’s backed into a corner and will likely retire this offseason for someone else to clean up.
With the contracts the way they are, the Sox aren’t going to have the financial wiggle room to add money. With the farm the way it is, you’re going to have to hope for shrewd cheap signings or deals if you’re to stay relevant in 2020. You’ll also have to hope for some rebounds from aging or diminished veterans.
If you go the rebuild route, the assets you have to trade come with enormous price tags, questionable performance or both. Betts is on the price tag side. He’s likely to see a near $30 mil price for his final arb season and has said he has no interest in extending before FA. That price tag and the single year of control will limit his return, but you still should get a young big leaguer or a single top 100 prospect. ERod has pitched to his peripherals for two consecutive years. This is the first year he’s neared a 6IP per start season even though his production tailed off this year compared to last. A change of scenery from the ALE and two years of arb control would probably make ERod your most tradeable asset. Another player likely to bring a return but only if the Sox eat money is JD. The guy can swing it for sure, but now a back issue has crept in. He’s not cheap and is likely not going to opt out. You’ll get some useful prospects for him, but likely guys far enough away or with a lowered ceiling to not be top 100 worthy off the rip. I don’t think you get anything for a year of JBJ. He’s gonna be non tendered IMO. Then there’s Beni. If there’s a rebuild, Beni is likely gonna go too. He’s a corner OFer with what will likely be a second consecutive 3+ WAR season. His offense is good. His defense is league average. What will limit Beni’s return will be his rising K rate, falling BB rate and ridiculous .360 BABIP. That being said, he’s got 3 arb years ahead which will increase his value and his return would be good. Workman is another guy who could return some value. He’s outpitched his peripherals yet has the single deadliest pitch in baseball. His OPSa vs the curve is lower than Bradley’s OPS in April of this year. Crazy good. He could return someone
Outside of these guys, anyone else you deal would be salary dumps or smaller deals of limited consequence. You’ll still be left with an enormously expensive club full of underachieving former stars. It will take 3 years for a big chunk of these contracts to go away and 6 more years for them all to expire (Xander is the longest controllable Red Sox, although you’ll probably want to keep him). This thing ain’t gonna be a one year thing. It’s going to be 3 years at least. Welcome to the cliff, DD pushed you off it this year