Former Manchester United assistant manager Mike Phelan believes Wayne Rooney could leave the club in the summer in search of a new challenge.
Rooney gave a transfer request at the end of last season, according to Sir Alex Ferguson, and is reportedly keen to test himself with another club.
The likes of Arsenal, Chelsea, Paris Saint-Germain, Barcelona and Real Madrid have been linked with moves for the 27-year-old, with the two English Premier League clubs reportedly showing the strongest interest.
New manager David Moyes, who gave the England international his debut with Everton as a teenager, is set to hold talks with Rooney to sort out his future.
However, Phelan, who left the club following the retirement of Ferguson last season, believes it might be difficult to persuade the player to stay at Old Trafford if he is adamant on moving on.
"Wayne is at the greatest club you can be at," Phelan told BBC Radio 5 Live. "Why would you want to jeopardise that?
"Unless you want a fresh challenge and you feel that challenge isn't being met at Manchester United.
"Every player is entitled to express a desire to want to move on. Any player can do that at any time.
"In Wayne's case, in the first instance in 2010, he took a lot of advice on that and got steered towards making that call but the manager was terrific. He talked to him and asked why would he want to leave the club?
"The press conference Sir Alex gave was a bit of a tear-jerker and it was genuine. There was an element that he'd chased this boy and paid big money. He was the boy that could change United."
Phelan might have been the right hand man of Ferguson for many years, but the 50-year-old insisted he has no idea what choice Rooney will make this summer.
"Somewhere down the line there will be words said, there will be meetings and they will see if it's still alive and worth going for or they'll call time on it," Phelan added.
"He's come from a fresh-faced 17-year-old and has been under the spotlight for that time and he has delivered. He might have hit a blip in certain performances but he isn't the first or last player to have done that.
"You have to nurse them through it and hopefully he responds to that. Sometimes you have to crack the whip with him. Wayne has responded as well as he feels he can do for United and what will be will be -- I haven't got a clue."
