I must say I am enjoying this season, even if my team didn't upgrade at the break. That being said, this is my post from 2017 predicting the 2020 closing of the window. Bradley and Sale fell off, which is why Sale signed for less money and Bradley is staring a DFA in the face. Bogey extended at cheap money for the sox. Kimbrel went packing. The sox did next to nothing in the draft and development range outside of getting Casas who is a long ways off. This 2019 team is seeing what a lack of depth and development gets you. Nobody to deal off for parts, no rookies to bring up to bolster the team's weaknesses. The sox farm is considered so bad that they are 30th in baseball with a "wide gap" between them and the 29th ranked team. The sox looked for pen options at the deadline, but teams had no interest in their minor leaguers due to either lack of production, ceiling, or proximity.
This is why I am glad Cashman didn't pay the insane prices being asked of him. When you deal off major talent for short term upgrades, you end up with a window and a cliff. The sox haven't had a cliff like this one in the Henry era. Theo and Cherries ALWAYS maintained a solid farm system. Even if the sox took a step back in farm rankings due to promotions, they were only a year off before the next wave replaced their losses. Yes, the sox spent 3 glorious years in last place since 2003, but during that time elite talents like Bogaerts, Betts, and Devers were making their way steadily up the chain or graduating to the club. Shrewd moves like dealing Miller for E-Rod helped replenish the depth and add to the team on graduation. The problem you have now is that DD shot the load and either graduated or traded every prospect with a pulse. He then brought in a development team that has failed immensely and the sox 2 scouting directors who have been utter disasters. The sox then spent a wild amount of money on players and extended others leaving them with no financial wiggle room for years to come. This leaves the sox in their current predicament. Farm is too bad to deal for any major upgrades, cap is too close for the sox to spend. Without a drastic deconstruction of some sort, the sox are staring at a prolonged and protracted rebuild.
One of the only ways I can foresee the sox jump starting this process is to actually lose enough to miss the playoffs this season and sell Betts. One year may not garner the type of return he would have a couple years back, but his return would be pretty substantial to a team with literally no depth. The only way that happens, though, is if the sox miss the POs by a wide margin. DD isn't the type to blow it up unless it is painfully obvious he needs to do that. If the sox win the WC or miss it by a game or 2, that may embolden DD to sell off whatever assets he has left to make one last push, which will deepen the cliff once Mookie leaves or gets paid.