#4 Simao
Another player who fell victim under Louis van Gaal’s reign, Simao’s spell at Barcelona was incredibly short-lived. Arriving in the summer of 1999 for a fee close to £11m, he partnered with fellow Portuguese star Luis Figo as Barca secured a second-place finish behind the vintage Deportivo La Coruna team.
Perhaps the most important moment for Simao was being overlooked by scenes elsewhere in the same game. The winger scored in a Clasico, now well remembered for when Figo was the subject of anger from Barca’s fans as he made the controversial switch. Simao scored in the 2-0 win, but never really kicked on afterwards and was soon out the door.
Van Gaal continued to freeze out the player and a move to Sporting CP was discussed. In the end, it was their city rivals Benfica who ended Simao’s misery at the Camp Nou.