Paul Scholes has admitted he was "devastated" when "best mate" Nicky Butt left Man Utd in 2004.
The pair came through United's youth ranks as part of the fabled 'Class of '92' brigade, along with Neville brothers Gary and Phil, David Beckham and Ryan Giggs.
That group formed a key part of United's success from the mid-'90s until Sir Alex Ferguson began to break up the side post-millenium.
Beckham was the first to go, joining Real Madrid in 2003, before Butt moved to Newcastle 12 months later, prior to the departures of Phil Neville to Everton and United captain Roy Keane the following year.
But despite outstaying a number of his close pals and other United stars, it was Butt's exit which hurt Scholes most.
"It was all part of football. When you start out with those five or six lads you hope that you’ll be there for the next 20 years," Scholes told DAZN.
"Unfortunately it doesn’t always work out that way. You lose people along the way. Nicky went and Nicky was my best mate – I’d grown up with him since I was 12 or 13. You’re devastated, I really was devastated."
Ferguson was no stranger to making big decisions regarding his players, having shipped out several big-name stars to make room for Scholes and co. as they graduated from the academy.
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Replacing the core of the treble-winning side of 1999 was no doubt Fergie's biggest task, though the legendary United boss was the master of knowing when to cut his players loose.
"Phil Neville went, Roy Keane went, some really big characters," Scholes continued. "Look players have to go they might come to a certain age where their legs weren’t quite what they were.
"The manager knew how to get the best out of those players, whether they’d play 20 games a season but he always knew when the time was right for them to go.
Who was United's best player from Fergie's '99 treble-winning crop? Have your say below.
"Sometimes the player didn’t always agree with that but that’s what it was all about; changing teams and then the excitement of bringing players in.
"You mention players there like Teddy [Sheringham], [Andy] Coley, [Dwight] Yorkey such brilliant attacking players and [Jaap] Stam – what a top centre half he was.
"He had a system and he just tried to replace the top players he had with other top players who were similar in that position. That’s why it was such a constant continuation of a being a top team."
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