He was a player legendary boss Sir Alex Ferguson signed in 1989 and was his assistant manager when he retired in 2013.
Phelan, who is a Lancashire native, had a short spell as manager of Hull City in 2016 but failed to replicate the success he had as an assistant, where he presided over the lauded training sessions with Rene Meulensteen and Carlos Quieroz that set the foundations for United’s dominant run in the mid to late 2000s.
As Ferguson’s right-hand man, United proved to be one of the best sides in European football, claiming three Premier League title wins, a Club World Cup, two League Cups and two runs to the final of the UEFA Champions League.
To the disappointment of Ferguson, David Moyes let go of Phelan’s services in 2013 and had been uninvolved with the club until Ole Gunnar Solskjaer requested his help in December 2018 as a first-team coach. In May 2019, Phelan was appointed United’s assistant manager, a full circle journey for the United legend.
And Phelan has reflected on the day Solskjaer got in contact and asked him to come back to Carrington, a day of great enjoyment for fans of United all over the planet.
“I was doing some coaching for the students when at one o’clock someone told me Jose Mourinho had lost his job,” he told The Mail on Sunday.
“There was another coaching session in the afternoon. When I got back to my car at four, I turned on my phone and ‘beep, beep, beep’. Ole wants to talk to you; so-and-so wants to talk to you, Sir Alex wouldn’t mind a phone call.
“It came out of nowhere. I took the calls for a couple of hours sitting in the college car park, deciding to go back to United to help Ole before I’d even talked it over with my wife. It was remarkable.
“Ole was a learner even as a player. I’d worked with him when he was reserves-team coach. And it got to a position where United found themselves needing someone who knew the club and been part of the history.
“They had gone outside of that after Sir Alex and I think the powers-that-be had a little look at themselves, thought how do they address it. That’s how it seemed.”
Phelan joined a United side as a player that had not won a trophy in over four years. Despite having a good side and a great manager, the Red Devils were in a period of transition, not dissimilar to the side Solksjaer took over in 2019.
“I can see and feel certain similarities,” Phelan added.
“The difference is at my age; I want everything to happen quickly. We’ve achieved a lot under Ole but not quite got it done, and every season, the expectation is magnified.
“We’ve done a lot of good things. There is definitely better harmony around the club, but the Premier League is a monster, massively competitive.
“I remember my time before we won anything. People would say, ‘You’re not as good as that George Best team’. It is amazing how quickly it dispersed once we’d started winning.
“Beating Crystal Palace in the FA Cup gave us a definite surge. When we won the league, there were tears from supporters, guys on the street, in the boardroom. It was unbelievable.
“There are similarities with where we are now. I do believe Man United can win something. When? I am not a fortune teller.”