3. Kevin-Prince Boateng
Boateng is one of the biggest wastes of talent in recent Tottenham history. His first manager Martin Jol was gone within a few months of his own arrival. The Dutchman’s replacement, Juande Ramos, handed him a run of appearances during that 2007-08 campaign but eventually decided he preferred others to the skilful Boateng.
Ramos’ apathy to the Ghanian was replicated by Harry Redknapp. Though the latter initially brought Boateng back in from the cold, he also soon decided the likes of Jermaine Jenas and Luka Modric were better suited to what he wanted.
Underlining the whole sorry affair, Boateng came back to haunt Spurs when he scored Portsmouth’s winner in their 2010 FA Cup semi-final.
With all the incredible footballing talent Brazil has produced over the years, Spurs somehow managed to end up with Sandro, Paulinho, Heurelho Gomes and Gilberto.
Acquired from Hertha Berlin for nearly £2m in 2008, Gilberto struggled immensely at Spurs and was substituted at half-time in three of his 10 appearances for the club before his contract was mutually terminated in 2009.
Capped by 35 times by his country in a career that lasted the best part of 20 years, Gilberto was not a bad player. But he was clearly unprepared for the task of making it in the Premier League, fulfilling the bad and largely unfair stereotype that long surrounded the ability of Brazilians to acclimatise to the English game.
1. Roberto Soldado
Following the world-record sale of Gareth Bale in summer 2013, Tottenham broke their transfer record three times. First they signed Paulinho for £17m in early July, before bringing in Soldado from Valencia for a fee of £26m (Erik Lamela signed for £28m later that summer).
Soldado worked hard for the team but seemed incapable of scoring goals – precisely the reason Spurs had spent the best part of £30m on him for. After two unsuccessful seasons in England, he returned to the Spanish top division with Villarreal.