I mean the broadly construed goal of that window was very clear - to give Mourinho the squad depth to fight on four fronts while extending as little financial commitment as possible given the lingering uncertainty of Covid.
Judged against that goal it was something less than a failure. Hart was an HGP backup goalkeeper who saw us through the games he had to and was sold for a fee after being signed as a free transfer. Bale scored some goals and sold some shirts and cost very little. Vinicius was arguably the most functional backup Harry Kane has ever had. All cheap short term deals that were wins as cheap short term deals.
The permanent moves up to the deadline were all cheapo moves. Hojbjerg could be had for KWP+3m. Doherty was an asset Wolves were happy to cash in on, and the Reguilon move had some interactivity with the Bale loan and also was made possible and cheaper by the buy-back which allowed Madrid all of the potential upside value. It was only a permanent deal to the extent Madrid wanted it to be and couldn't extract more by taking him back.
And then Rodon was an after-window scoop from the EFL level (do they still have a different deadline or was that just a Covid thing?) that seemed to be about assuaging Mourinho's anger that the CB hole hadn't been filled.
And course we also failed to sell a single player besides KWP from a squad that was very obviously filling with deadwood. That was our best opportunity to escape from the Ndombele situation, among others.
That window was a short-term project in the same way Mourinho was a short term project. Both projects failed. It should be no surprise we haven't generated long term benefit from that window when we weren't even intending to!
Our moves are plotted with a bit more coherence under Paratici. But the overhang of the empty 2018, the blunder of 2019, and the immediate season-focused 2020 still leaves us well short, and the pace of the overhaul is not sufficient to get us back to where we were in 2017, let alone kicking on a level beyond that as we had the chance to do.
