Sir Alex Ferguson has revealed that the sales of Phil Neville and Nicky Butt represented two of the toughest decisions of his 24-year Manchester United tenure.
Neville and Butt were part of a group of United academy graduates known as 'Fergie's Fledglings', youth-team players who were given an early first-team break by Ferguson and went on to become the backbone of the club's successful sides of the 1990s and early 2000s.
But as part of the evolution of Ferguson's side in the mid-noughties, the United boss allowed Butt to leave the club for Newcastle in 2004 and Phil Neville to join Everton in 2005 as he rebuilt a new team.
And Ferguson admits that letting the pair - who played 98 England internationals between them - leave the club was a real wrench.
"It's a horrible part of the job, Ferguson told ESPN in an exclusive interview. "You become a family really, you protect them that way your father would with his son. It hurt me terribly at the time because they were fantastic professionals with Manchester United roots.
"Phil Neville and Nicky Butt were part of the start here there's no question about that, people may identify Manchester United in many ways, by the great players they've had, by the players that were signed but the real secret is the players who have brought that spirit to Manchester United; Phil Neville and Nicky Butt were part of that.
"When the time came for me to advise them to move on because when they weren't playing regularly, it wasn't easy for me it wasn't easy for them. So the advice I gave them was 'look you really need to get regular football in'... we did the best we could for them and I think we got them good moves.
Ferguson believes that he has had to adapt his approach to dealing with players over the years, and says the modern-day footballer needs more careful handling than those in years gone by.
"You must change, you have to adopt,adapt to the changes to the individuals and the characters of the people we deal with now," Ferguson said. "It's a different human being we're dealing with now, it's a much more fragile human being.
"The people I'm dealing with nowadays seem to be more cocooned by their pay or their agents or their egos so you have a different person all together. So dealing with that you have to be different."