It seems that, in their evolution, they got caught up in the need to buy talent who had impressed in the past, and despite the obvious red flags, they still would stump up the money.
These prices seem more trivial now that they are back in the top flight, but at the time they could have been devastating in their promotion push.
One transfer in particular which fits this bill is the purchase of Helder Costa, which was very reactionary given that he had been on loan the season prior and disappointed.
Across 43 Championship games in 2019/20, he scored just four times and assisted a further six goals, which makes the decision to unload £16m on the Wolverhampton Wanderers reject even more baffling, especially given how Leeds were now making the step up to play even tougher football.
The Angola international unsurprisingly wilted further during the 2020/21 campaign, featuring just 22 times in the Premier League as he scored just three goals, two of which came in their second game of the season.
Despite spending three years at the club, he featured just 71 times, while also enduring some poor loan spells in an attempt to reignite his career.
It is a testament to how far he was fallen that, just this summer, he was finally shipped off to Al-Ittihad, with the Whites resigned to making a 75% loss on him as he left for a mere £3.9m.
Following Costa’s exit, former England goalkeeper Paul Robinson had some choice words to say about the 28-year-old’s disappointing stay at Elland Road.
He claimed of the Angolan: “He hasn’t been able to do it at the level that Leeds wanted him to do it at. When you’re selling a player, you’re only going to command top money from top teams and if he’s not been good enough at Leeds, you can’t demand top money from elsewhere.”
Costa promised much when he moved to Yorkshire, but in all honesty, he has been a huge flop who drained the club in his time at Elland Road.