I wonder how realistic an option it was for them to start cutting salary at this trade deadline this year. Despite bad years, June/July could have been a time to deal Porcello and Bradley. Beyond that, making the leap with JD at the same time could have resulted in a 2019 reset. Going into the trade deadline, I at least thought this was a possibility and in hindsight would have been the better move than trying to reset in 2020.
Prior to the World Series victory, there wasn't much about Dombrowski that I could legitimately complain about. I wasn't a fan of dealing the farm or not creating a bullpen, but in hindsight non of the farmhands are biting us in the butt yet. Obviously since then we have Sale and Eovaldi as questionable moves, but I'd also like to consider the non-firesale as something that should be partially on him as well.
We are also all looking at this as a 2020 problem, but if they're unable to do it in 2020, it looks like 2021 is an even tougher issue.