Every club can have a nightmare in terms of incomings but it seems to have happened at Sunderland more often than not over the years.
But the club now seems to have changed tact with sporting director Kristjaan Speakman taking the club in a new direction.
Recently, Speakman insisted Sunderland will not compromise on quality in the closing weeks of the transfer window.
He also stressed that he believes the club will get the business they need to challenge for promotion done.
In an exclusive in-depth interview, Speakman told The Echo that while encouraged by progress on the pitch, there is no doubt that the club still have work to do before the window closes.
"On the field, we're really comfortable with the progress that we're making," Speakman said.
"You want to try and change the style of play to something that people want to come and watch, and I think you can tangibly see we're working towards that as we change the personnel, the head coach gets time to work with the players etc.
"I was on the record last season saying that it can be difficult to achieve that when you have those performance markers every Saturday and Tuesday, with next to no training time in between.
"Off the pitch, we want to make a few more signings to address the areas where we feel we're in need of extra players. Stuart [Harvey] and the guys and as a team, we're working really hard to do that."
The deadline for the Black Cats to bring in new additions to Lee Johnson’s squad will pass in September 7, with seven players already through the doors at the Stadium of Light.
Here, though, we take a look at some of Sunderland’s worst signings from years gone by as the club finally books its ideas up in the market.

13. Jozy Altidore
Signed for £8m when the Black Cats were in the Premier League. More to the point, how did Sunderland manage to actually convince Toronto FC to swap Jozy Altidore for Jermain Defoe? Photo: Mike Hewitt

14. Will Grigg
It hasn't gone well for him, has it? A £3m deadline day signing from Wigan Athletic with the hilarity of at all captured by Netflix's cameras for the world to see. Brilliant. Photo: Stu Forster

15. Nicolas Medina
Nicolas Medina signed for Sunderland for £3.5m, joining up with Argentine youth team colleague Julio Arca. At his signing, manager Peter Reid hailed him as "a complete midfield player". He failed to make a league appearance at the Stadium of Light. Photo: Ben Radford

16. Liam Bridcutt
Two seasons of mediocrity before heading out to Leeds United on loan, eventually penning a permanent deal. Signed by Guy Poyet for around £3m. Photo: OLI SCARFF


