Eamon Dunphy believes that Jose Mourinho's personality and a lack of control over transfer policy means the Portuguese will not restore Manchester United to their former glory.
The Red Devils will only qualify for next season's Champions League if they beat Ajax in the Europa League final on 24 May.
Mourinho has openly criticised members of his squad several times as the chance of a title tilt in his first season at the club evaporated.
RTÉ soccer analyst Dunphy says the bond he forged with his original Premier League-winning Chelsea side (2004/5, 2005/6) has not been apparent in subsequent jobs.
"It's always about Mourinho in Mourinho's mind"
"He had it with the players in the old Chelsea team, with Drogba, Lampard, Terry..." Dunphy told RTÉ 2fm's Game On.
"I think there was a very close bond between him and the players at Chelsea in that era.
"But his relationship with players at Real Madrid was difficult. I think even at Porto, possibly, relations weren't great.
"It's always about Mourinho in Mourinho's mind.
"I think serious men, which footballers are, don't like that and you alienate them.
"When you have players like (Diego) Costa, (Eden) Hazard, Fabregas, these are experienced men and they don't like seeing the manager out front and centre all the time.
"This is why he doesn't stay anywhere very long and why he's the wrong man for Manchester United."
Mourinho walked out of an interview with Sky Sports Geoff Shreeves on Sunday when he was asked what Manchester United needed to do to challenge for the Premier League title next season.
Dunphy suggested that world-record signing Paul Pogba was not the manager's choice and that he was starting to realise the impossibility of his task.
"I'd say he's very frustrated; that's why he turned on Geoff Shreeves yesterday.
"The chief executive Ed Woodward clearly buys the players. If Pogba wasn't his (Mourinho's signing) where do they go next?
"Once players know that you're not the man in charge, you're dead."