Henry Winter says Wayne Rooney would be foolish to leave Manchester United for Chelsea - or any other club - this summer.
Speculation has been rife over the future of the England forward after Sir Alex Ferguson left him out of his final home game in charge of Manchester United last week, indicating that the player had asked to leave Old Trafford.
This week's Sunday Mirror has linked Rooney with a switch to Premier League rivals Chelsea, while the Star on Sunday suggested he could be heading to Monaco, but Winter says he should look to build a legacy for himself in Manchester.
"The grass isn't always greener," said the Daily Telegraph Football Correspondent.
"He is on a fantastic financial contract at Manchester United, he is at comfortably the most successful club and team in the country and he can do great things there.
"He should look at what Frank Lampard's just done with Bobby Tamling's record. Lampard is now a total legend at Chelsea and if Rooney continues at the current rate of goal return, even slightly diminished, he could conceivably overtake Bobby Charlton by the time he is 30 or 31.
"Rooney has to think of his legacy and has to think about whether the grass is always greener. Can I see Rooney settling in to life in Monaco or Paris or Madrid? Not particularly; his family is in the North West and is settled there.
"I think he needs to look again. I think he needs to talk to his advisers and to his wife and family and say the best thing he can do is knuckle down and stay at Manchester United.
"There were obviously issues with Ferguson, but Ferguson is now gone. He's had previous issues with Moyes that ended up in the courts but they've since cleared that and Moyes knows Rooney well. Next season, if he can focus and knuckle down it could be a new era for Wayne Rooney at Manchester United.
"I think he needs to think long term. Would he be happy at Chelsea? I don't think he would."
Rooney has played in midfield several times this season and has apparently been frustrated by being asked to play in a range of positions.
He was left out of the home leg of United's Champions League clash with Real Madrid, but Winter argued that those selection and positional issues could easily arise again if he moved to Chelsea.
"Where does he go?" he asked.
"You talk about Chelsea, but they play 4-2-3-1 and the three are pretty much established - Oscar, Juan Mata and Eden Hazard. So is he going to take the number nine role there?
"Obviously Fernando Torres is there, they've got Demba Ba and Romelu Lukaku comes back from West Brom.
"He has to think logically. I agree that Rooney loves playing and that is his huge passion, but is he going to start every game for Chelsea?"