2. Cameron Stewart
With Brian McDermott desperate to add some width to his attack in January 2014, Leeds pulled off what on the face of things appeared decent deals for Jimmy Kebe and Stewart.
A week after being dumped out of the FA Cup by Rochdale, the duo made their debuts as Leeds were thrashed 6-0 at Sheffield Wednesday as McDermott pioneered the 3-4-3 formation Antonio Conte replicated to great success with Chelsea.
Stewart had joined on loan with a three-year contract already agreed to begin come the end of the season. He was so bad, Leeds reneged on the deal, and the former Manchester United man took legal action against the Whites.
1. Seth Johnson
Having starred for Derby County, Johnson was being tipped as the future of England’s midfield. As a result Leeds forked out £7 million for his services.
Injuries plagued his time in West Yorkshire, though, and he made just 54 league appearances in four seasons with the club. His massive wages, meanwhile, are cited as the best illustration of the mass overspending that crippled the Whites during the early 21st century.
Checkout : Greatest Leeds United Players Of All Time