Despite being a leading performer for Benfica and Atletico Madrid, there is a sense the winger’s chance of making it at the very top echelons of European football has been and gone.
After starting at Sporting Lisbon, a €15m (£12.4m) transfer took him to Barcelona as a 19-year-old in 1999.
Under Louis van Gaal he endured a frustrating two years at the Nou Camp and returned to Lisbon, this time with Benfica. He rebuilt his reputation with 76 goals in 172 games at the Stadium of Light and commanded another huge fee when he left to try his luck in La Liga again at Atletico in 2007.
He has been a solid performer in Madrid and helped them to Europa League success this season. Ironically Atletico knocked Liverpool out in the semi-finals, a club that had courted Simao for years.
He was Portugal’s top scorer in qualifying for South Africa, but due to the form of Nani he is not guaranteed a starting spot in the Portugal team.
During his time at Benfica he never missed a penalty and recently released a DVD called Como Se Faz um Campeão (How To Make A Champion) to teach children basic skills of football.
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