Nobody interested in the job looks at the Cherrington departure as a reason for not thinking Boston is a good fit, so this whole 2 GMs in 6 years rant is bogus.
Nobody interested in the job and knowing the Sox are looking to rebuild sees the DD departure as something to worry about anymore than they would entering any other GM position.
The Sox job is one of the most coveted jobs in MLB, if not all of organized sports.
Henry is one of the most respected owners in all of sports. There's a very nice core of players to work with. Sure, there are financial issues, health issues and a tough 2020 season coming up, but if you are a good GM, you'd love to be taking over this team. If the reset is a major priority for 2020, there is no pressure to win it all in 2020 and probably 2021 as well.
We'll be able to pick who we want, and the choices will be from the best of the best that are available.
Some may think Theo or other ex-Sox execs are the best, but maybe that's not who we want.