Michael Owen
Liverpool’s poor performances in the Premier League and Owen’s desire to be playing regular Champions League football led to a large amount of transfer speculation in the early 2000s. When Houllier was sacked in 2004, the final ties holding Owen to Anfield appeared to be broken. Rafael Benitez left him on the bench for a European qualifier and he sealed a move to Real Madrid a couple of days later, having run his contract down to its final year.
We made just £8m for the sale of Owen, arguably one of the best players on the planet at that stage, and ironically we’d go on to win the Champions League at the end of that season. The striker completed his fall from hero to villain when he eventually joined our arch rivals, Manchester United, in 2009.
Pepe Reina
Reina set his heart on returning to Barcelona, his boyhood club, having been told that Victor Valdes was leaving for Monaco. In anticipation of the move going ahead the Reds signed Simon Mignolet from Sunderland as his replacement. Unfortunately for Reina, Valdes decided to stay and Barcelona pulled out of the deal. The Spaniard eventually joined Napoli on a season-long loan deal, but the damage was done and he never played for us again.
He sealed a permanent switch last summer when he joined Bayern Munich. He made just a couple of appearances in all competitions and was sent-off in the later after just 14 minutes. He’s since completed a move back to Napoli on a permanent basis.
