Leeds United have made plenty of high-profile transfers over their illustrious history, many of which were bound to be blunders.
However, trawling back to before their 2004 relegation, there were a clear number of missteps that resulted in their surprise demotion.
Whilst one might be losing key men, another certainly has to be some of their questionable incomings that financially hampered the club.
One such transfer was when David O’Leary decided to fork out £4m in 1999 on Darren Huckerby.
Brought in to solve their striker crisis, he offered little in the way of goals across his season-and-a-half stay in Yorkshire.
The fact they managed to recoup anything for him was sensational, given how awful he was for them.
Regardless, they still had to pay £650k for every goal he scored for the club before his exit.
It is clear that he was not solely disappointing for O’Leary though, as he butted heads with Glenn Roeder during his stint at Norwich City.
He had just produced what he described as a “horrendous” performance, something which Leeds fans would be well used to, to which he received a dressing down far worse than anything he had ever received from a manager before.
To his credit, whilst playing at Elland Road he was competing with the likes of Alan Smith, Mark Viduka and Michael Bridges, who are some of the better strikers that have graced that pitch.
However, when he was handed the chance to be their main man, he floundered.
It marked a shocking piece of business, which surely will have contributed to their need to sell off their key assets.