Fernando Torres Liverpool to Chelsea (2011) - $77.7 Million
A classic cautionary tale of what can go wrong with a record signing. In the late 2000's, Torres was one of the most impressive strikers in the English Premier League. His quick turn of pace put him behind defenses seemingly at will. But in 2011, as his move to Chelsea drew near, Torres was a man recovering from a bad knee injury. While theoretically in his prime, the injury seemed to have robbed Torres of his main gift.
But Chelsea owner Roman Abramovich is not the sort to be dissuaded. He needed a striker to replace the aging Didier Drogba and he needed a star to fill the stands. Torres was purchased for £50 million (and in the process accidentally made lumbering Andy Carroll, Soccer's Tim Tebow, a £35 million Striker) and two and a half years later it's hard not to call this a bad investment.