#2 Manuel Rui Costa, Fiorentina, 1994 – 2001
Of all the players on this list, Rui Costa is probably the most popular, however, it's your writer's opinion that he was so incredibly good that he should be discussed on a weekly basis as opposed to only when a new Portuguese wonder-kid breaks on to the scene, and the former Fiorentina and AC Milan ace is uniformly brought up as a means of comparison.
He arrived in Florence from Benfica in 1994 and quickly established himself as one of the finest footballers of his generation, earning himself the recognition of Brazilian legend, Pele, who named him one of the 125 Greatest Living Footballers in 2004.
The Maestro (as he was known) generally operated as an attacking-midfielder but due to his touch, creativity, and work-rate, he was more than capable of dropping deep to orchestrate play, too.
The Portuguese ace moved to Milan in the later stages of his career, and it was at the San Siro where his incredible skill would finally be rewarded. He lifted the UEFA Champions League in 02/03 as part of an experienced Milan side that overcame great rivals Juventus in the first ever all Italian final at Old Trafford. The same side went on to lift l Scuddeto in the 03/04 season.
However, it is in Florence, where he played with Argentinian goal-machine, Gabriel Batistuta, that most of us remember his genius: the tricks, the chip shots, the flicks, the eye of a needle passes, the turns, the long-range strikes, and the rest. Manuel Rui Costa was unplayable on his day in the famous Viola of Fiorentina, where he spent 7 seasons, scoring 38 times and registering 9 assists in 215 Serie A appearances.
The skillful midfielder went on to inspire the next generation of Portuguese talent, including a young boy from the island of Madeira, named Cristiano...
"At that age, I was looking at a big reference in the national team, for example (Luis) Figo, Rui Costa, Fernando Couto. It was kind of a dream to reach that level."