Phillipe Coutinho
Coutinho became one of the most exciting players in the world during his time with Liverpool. However, everything when Barcelona displayed an interest in the Brazilian midfielder. He dreamed of moving to Spain and playing with his national teammate, Neymar. Coutinho put pressure on the Reds in a bid to force a sale.

In the end, he received his wish but it didn’t work out well for him. On paper, he won many trophies but it tarnished his legacy. Coutinho became a fringe player and went on loan to Bayern Munich. Meanwhile, Liverpool reinvested their earnings in the team and took a giant step forward (via The Athletic).