#4 Ricardo Quaresma
Born just under two years before Cristiano Ronaldo, Portuguese winger Quaresma was once seen as having the potential to rule the world just as his countryman has done. In 2003 at just 20, after two outstanding seasons with Sporting CP, he was signed by Barcelona, and while that move didn’t work out, a move back home to Porto in 2004 proved to be far more fruitful.
While he came under some criticism for being a selfish player, Quaresma was one of Porto’s key men during his four seasons there, three of which saw the club win the Portuguese Primeira Liga. He was a surprising omission from Portugal’s 2006 World Cup squad, but at his peak between 2005 and 2007, he was considered one of the most exciting players in the world.
From there, however, it largely went downhill. He signed with Inter Milan but didn’t get on with then-boss Jose Mourinho, who thought he was undisciplined and selfish. A 2009 loan move to Chelsea proved pointless as he only made five appearances and upon his return to Inter, the Italians struggled to offload him.
Since then, he’s lived up to his nickname ‘Cigano’ (gypsy), moving from Besiktas in Turkey to Al-Ahli in Abu Dhabi and then back to Porto and finally Besiktas again. While he’s had some success along the way, he’s never come close to his mid-2000s’ peak, although he did play a surprisingly key role in Portugal’s Euro 2016 triumph.