Nani was absolutely delighted when he signed a contract extension with Manchester United in September 2013.
"Playing at United has been a fantastic experience for me,” the player gushed at the time. “When I came to the club, I never imagined the success we have enjoyed.”
Three years on and Nani now considers his decision to commit to United as the “worst” moment of his life.
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Four months before putting pen to paper on a new five-year deal, Nani witnessed as David Moyes was appointed Sir Alex Ferguson’s successor at Old Trafford.
It was supposed to be the start of a bright new era but things quickly went downhill for Nani, who only started seven Premier League games in 2013-14.
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The Portuguese winger, who left United permanently last year, expected to become a central figure in Moyes’ side, but was instead cast aside as injuries and poor form affected his season.
“It could have been the best moment of my life but it turned into the worst,” Nani told The Guardian. “After you sign a contract like that, you think all the people will be behind you and help you. And you see the opposite.
“Then the stress comes. I was down and, when it’s like that, of course, the injuries come too. It was a bad moment. It was something that made me very down, very disappointed.”
Shop window tactic
Moyes was sacked in April 2014 after a torrid 10-month spell, and one of his final acts was to start Nani in his final game in charge in an apparent shop window tactic.
Though the Scot wasn’t around to see it, his plan worked. He joined Sporting Lisbon on loan in August 2014 after being told by Louis van Gaal, Moyes’ replacement, that he faced an uphill battle to start.
“[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 continued.
“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.”
Nani didn’t stick around long after returning from Sporting Lisbon. He signed for Fenerbahce in July 2015, bringing to an end a rollercoaster eight years in Manchester.
There are, of course, plenty of positives from his time at United. Nani won four Premier League titles and the Champions League, and was also included in the PFA Premier League Team of the Year in 2010-11.
Yet it’s evident that the winger, who signed for Valencia in the summer, still feels a tinge of regret about the final chapters of his United career.