Mark Wood says...
For me, hands down and the most shocking when you remember what was needed was the Martin Bain/Chris Coleman January window in 2018. At the end of December, we had just picked up a desperately needed win at Nottingham Forest and sat in 21st place in the Championship. With the window open, a few good well thought signings could have given us an injection of the quality we needed to pull us out of the drop zone and the Sunderland we know today would not have spent four long years in League One.
All reports coming out of the club were that Ellis Short was not willing to spend a penny on transfers as he looked to offload the club to a new owner. And really not a penny. Nothing for transfer fees, not for signing on fees, not even loan fees. This meant, that any player available for a small transfer fee was out of our reach.
Any club looking to loan a player out would put Sunderland bottom of the list of any potential suitors. I don’t blame Bain or Coleman, they could only work within the parameters that they were given, but we ended up bringing in Lee Camp, the red misted Jake Clarke-Salter, Ashley Fletcher, Lua Lua and he never even got fit enough to start a game. We are still paying the price today for that window.
Perhaps I say this with the benefit of hindsight, but the January window in 2019 sticks out like a sore thumb for me, for a number of reasons.
We held a live Podcast as the news came in on January deadline day that year that we had finally beaten the clock to sign Will Grigg, and after a frustrating month where we lost our top scorer in Josh Maja, and then spent the final days (and hours) of the window scrambling around to find a replacement, there was an enormous sense of relief when we finally got our man.
As things transpired, the Grigg transfer was (and still is, given he’s technically still our player) an absolute disaster, and later seeing the way Stewart Donald caved into Wigan’s demands on the second series of Sunderland Til I Die only compounded my misery surrounding the way the situation turned out.
Lots of valuable lessons were learned as a result, and I think that the current people in charge of our recruitment will have taken lots from the disastrous way in which Stewart Donald and the Eastleigh mafia royally cocked up our season with their incompetence in that particular window.
Rich Speight says...
Transfer windows are only really memorable in retrospect, as far as I’m concerned. The actual process is, for a fan, one of a sustained period of low-level background anxiety tinged with both hope and trepidation. Once completed, one almost wishes to forget that the actual window ever happened and just get on with supporting whichever players have been recruited and hope they can do the job they’ve been recruited to do - which invariably is to either fight off relegation or achieve promotion.
So on that level, January 2007 has to count as a pretty successful window. Roy Keane took the club from mid-table in the Championship on an unbeaten run that saw us promoted back to the Premier League in first place. The additions of Carlos Edwards, Danny Simpson, and Jonny Evans and the permanent transfer of the late Marton Fulop were clearly very shrewd indeed, and Stern John and even Anthony Stokes played their part during that campaign.
We also got rid of one or two players who didn’t cut the mustard in one way or another, including permanently offloading pre-long-throw-in edition Rory Delap and finally calling an end to the torturous time of Jonathan Stead.
As for the worst one... 2019, whilst undoubtedly dramatic and making for riveting boxset viewing, was ultimately disastrous and has an impact that is still felt (financially at least) today. Will Grigg - the most expensive player in third-tier history - and Kaz Sterling were no replacement for Josh Maja’s goalscoring prowess or potential value, even if the midfield was arguably improved a little with Grant Leadbitter’s return. The loan spells of Lewis Morgan and Jimmy Dunne were pretty patchy, and ultimately the squad fell short of the goal of promotion and we achieved what was - up to that point - our lowest ever league position.