Luis Carlos Almeida da Cunha, also known as Nani, was one of the most divisive players to pull on a Manchester United jersey during his time at the club, but the longer he stayed, the number of fans defending his corner appeared to deplete.
For every moment of magic came a dozen shots that threatened to harm the people in the nosebleed seats behind either goal, and when Nani signed a 5-year contract extension in David Moyes' only season in charge, the decision was met with bemusement.
Even Nani's biggest fans could see that a five-year deal was strange, but now the man himself has come out and claimed that it was the worst moment of his life while speaking to The Guardian.
It could have been the best moment of my life but it turned into the worst.
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.
Even during his best performances for the club it seemed like there were a section of United supporters who simply could not warm to the Portuguese, but as David Moyes left and Louis Van Gaal was brought in it became clear that he would be heading for the exit door before too long.
Nani simply didn't fit into Louis Van Gaal's now infamous philosophy, so when the time came to move on it made the decision to award him a long contract all the more confusing.
If there was any hope for Nani to stay at United, then that was squashed when the Dutchman told Nani that he would have to accept the fact that he was not even considered second choice if he wanted to fight for his place.
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.
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 would have to relocate to Turkey to ensure the first team football that he was after.
The move was initially criticised as some felt that he was taking an easier option and perhaps one motivated by the financial side of things, but Nani did play regular football and has now secured himself a move to Valencia with a Euro 2016 winner's medal around his neck.
Things have taken an upward turn for Nani, but he still looks back on his departure from Manchester United as an unfortunate period in his life, while still acknowledging how important his time there was. Interestingly, Nani gave his take on comparisons to Cristiano Ronaldo which inevitably popped up after he followed his compatriot to Old Trafford.
United gave me all that I have in this life.
They were expecting me to be the next Ronaldo but that’s unfair. We are different players, different personalities. Maybe it was a mistake to compare us.
You can read Nani's interview with The Guardian in full for more including his feelings on Sir Alex Ferguson.
