With Nani moving to Major League Soccer side Orlando City, we look at where he's been since he left Manchester United, and assess if he could be a hit Stateside.
Nani labelled Sir Alex Ferguson a "father figure" after winning eight major trophies with United, but managerial changes saw him leave Old Trafford permanently in 2015.
Nearly four years on and Orlando have signed the ex-United winger from Sporting Lisbon on a free transfer - on a three-year deal - as they prepare for the new MLS season, which kicks off on Saturday.
But where has Nani been since he left United and why have Orlando decided he would be the right fit for them? We take a closer look...
Why did Nani leave United?
Nani was brought to United by Ferguson in 2007 and helped them win four Premier League titles, the Champions League, the FIFA Club World Cup and two League Cups, but he left Manchester as a player on the fringes.
After signing a new five-year contract at Old Trafford in September 2013, he started only seven matches for United under David Moyes.
But even then, he was still eager to succeed under the Scotsman's successor Louis van Gaal. However, it soon became clear to the Portugal international that he needed to cut ties to pursue regular first-team football.
"He [Van Gaal] told me that, if I wanted to stay to fight for a position, then good but I would not be his first option or maybe even the second," Nani told The Guardian in 2016.
"I said: 'No. I have been here for many years, I have been very important to this club and I think it's time to decide.' I wanted to play every game in the starting XI."
Moving around Europe
Nani has played in Portugal, Turkey, Spain and Italy since leaving United. He moved back on a season-long loan to his hometown club Sporting Lisbon, as part of a Marcos Rojo swap deal, following an unsuccessful World Cup with the national team.
His move back to his native country was met with great enthusiasm. He enjoyed a prolific season, particularly in Europe where he scored four goals in seven appearances, which caught the eye of Fenerbahce. In July 2015, the Turkish Super Lig club signed him for £4.25m and entrusted the experienced winger with a three-year contract.
With Nani eager to rebuild his reputation as a consistent performer, his productive debut campaign in Turkey saw him enter Euro 2016 in strong form.
He finished the summer a European champion and captained Portugal in the final with injured talisman - and close friend - Cristiano Ronaldo watching on from the touchline.
The Portugal team's memorable summer put Nani's name back in the European headlines, and it was Valencia who were next to take a chance on him. But he was in and out of their starting XI during the 2016/17 season before a disappointing season-long loan at Lazio saw him left out of Portugal's 23-man squad for the Russia World Cup.
It was that exclusion which seemed to spark another career move back to Sporting in the summer. He has scored eight goals in 24 appearances this season and started in both Europa League group games against Arsenal.
Why did Orlando go for him?
Orlando City finished bottom of the MLS eastern conference last season as they struggled to adapt to life without star striker Cyle Larin, who switched to Besiktas in January last year.
Kaka, who helped put one of MLS' newer franchises on the global map, departed at the end of 2017 and the Florida-based club have had one of their three Designated Player spots left open ever since.
With a slot free to bring in a marquee player, the MLS outfit have chosen Nani to add elite European experience to fill that exact void left open since Kaka's departure.
"This is an exciting day for our organisation," said Orlando City EVP of Soccer Operations Luiz Muzzi in the club's official unveiling statement.
"Nani brings tremendous experience to our roster. He's a dynamic winger with quality abilities to move and cross the ball, impact games and lead the offensive play."
Has he still got it?
Nani will likely start his MLS career either in a strike partnership with former Norwich City academy striker Dominic Dwyer, who is a marquee player, or in his natural position on the left wing.
Orlando's Irish boss James O'Connor has used a 5-3-2 in pre-season ahead of their MLS opener against New York City on March 2, but he could decide to move to a 4-3-3 to accommodate his Portuguese star.
Orlando are full of central midfield options, including US international - and designated player - Sacha Kljestan, meaning O'Connor may have been keen to find a wide player.
However, it is no secret Nani has lost a bit of pace despite contributing nine goals and seven appearances in all competitions for Sporting in the 18/19 season.
Nani's move to MLS at his age, in a time when most of the league's teams are looking for younger stars, may raise some questions marks among the American press.
But if he can help improve Orlando, similar to how his former team-mate Wayne Rooney has rejuvenated DC United, then he will surely become a fan favourite.