In hindsight, we can definitively say we could have won in 2018 without Pom, Thornburg and Reed, but that's not really fair. We could probably add the Kinsler-Buttrey trade and say, we'd still have won. Sale & Kimbrel didn't really do all that much in the playoffs, but without one of them the whole season might have gone differently.
I'm thinking, to win in this league, you have to build a roster that looks like "overboard," so you can handle injuries, unexpected down years or under perfromances and just the plain luck involved with the "crap shoot playoffs."
I do think DD went to far, but it worked, so I'm fine with what he did.
I also realize we now have to pay the consequences for what he did, and I'm not going to sugar coat it. It sucks, but it's worth it. The 2018 ring was wonderful. Sure, I wish the window stayed open another year or two, but it is what it is. It's not the first time I really liked a Sox team and felt they were going to win it all (or had a great chance) but ended up disappointed. It won't be the last.
I liked our chances in 2003, 2006, 2008, 2009, 2010, 2011, 2012, 2014, 2015, 2016, 2017 and 2019.
I'm okay with not really like our chances much for 2020- not that I won't.