#6 Gareth Bale - Tottenham Hotspur to Real Madrid

Daniel Levy is one of the best negotiators in football, and when Tottenham managed to negotiate a world record fee for Gareth Bale, plenty of praise came his way. The Welshman was undoubtedly one of the best players in the world, but managing to get €101 million in 2013 was downright brilliant.
So much so, that Real Madrid denied all reports of being the first team to have ever breached the €100m mark - so as to placate Cristiano Ronaldo. FootballLeaks managed to reveal the truth years later, which confirmed Bale's massive fee.
In the 5 seasons he's spent at the Bernabeu, Gareth Bale's quality has not been in question. However, since Bale's injury record has been quite awful, you could comfortably justify that Madrid have been short-changed.
As for Spurs, they did not use that money to the best of their ability, so it seems this was a lose-lose all round.
Fee Paid: €14.7m
Fee Sold: €101m
Profit: €86.3m