It’s not DD’s fault Betts turned down an offer, or is all about money, but the contract situation they have is certainly his doing, as is the depleted farm. These were my main gripes about Dombrowski when the Sox hired him - he signs players to absurd contracts, and he empties farm systems.
Also, the albatross situation after 2020 is the same - the Sox will still have 4 (Price, Eovaldi, Sale, Pedroia). Castillo doesn’t matter