So it’s back to the future for Jack Wilshere.
He was the beating heart of Arsenal’s Under-18s, the star boy of the club’s academy, when they triumphed in the 2008/09 FA Youth Cup.
In a few weeks’ time, Wilshere will lead the current crop into another final – in his first season as head coach.
Arsenal haven’t won this trophy since that 6-2 win over Liverpool 14 years ago.
In that time, Wilshere secured major silverware with the club and represented England at the World Cup.
And yet, his verdict after Tuesday night’s semi-final, after Myles Lewis-Skelly’s 120th-minute winner over Manchester City?
‘For me, right now, it feels like one of the top moments of my career,’ Wilshere said.
‘It’s obviously fresh, but that feeling… I can’t even explain what it feels like, that moment. Relief, joy, love for the players, emotions – everything.’
He added: ‘Obviously as a coach as I am a young coach, but as a player as well, it feels like it’s up there.’
Wilshere struggled to describe the chaos in the dying moments of full-time when the outstanding Lewis-Skelly, only 16, headed in a dramatic winner and the Arsenal bench flooded on to the pitch.
‘I can’t remember,’ he smiled.
He should be used to it by now - drama has seeped into every stage of his team’s run to the final.
This was Arsenal’s third late winner. They have had to come from behind at times, too.
‘This team keep doing it,’ the 31-year-old added.
‘I don’t know how many times I said it but how much belief they have, I see it in them… they’re so good and easily coachable that this creates a belief within them.
‘You see it, they keep pushing at the end and they scare me because they leave a one-on-one in the backline but they want to attack.
‘As a coach, I’ll go to the West Ham-Southampton (semi-final) on Thursday and whoever it is I’ll think: ‘How can we beat them, how can we score a goal’ and I see that in this team.
‘Sometimes we have to defend our goal first and we go from there but I love that spirit: “Let’s go and score a goal”.’
They might have made this night easier for themselves – given Michal Rosiak gave Arsenal an early lead after Lakyle Samuel was sent off for City.
Unfortunately, the 10 men would not lie down and City had several good chances before Justin Oboavwoduo sent the game to extra-time.
This season, though, adversity has been stitched into the success of the Arsenal men’s and women’s teams, as well as this promising bunch.
‘I think back to my days as a player and that’s in the Arsenal DNA,’ said Wilshere, who first joined the club aged nine.
‘You walk around the training ground and you see: “Never give up”, ”Play until the end”, quotes from Arsene Wenger.
‘When you play for Arsenal, you fight until the end. Mikel (Arteta) has done a top job of building on that and getting this winning feeling through the whole club. If the first team keep raising the bar, we have to otherwise the gap gets too big. We have to keep pushing and we did that well.’
Their reward? Another run-out at the Emirates against either West Ham or Southampton.
The crowd on Tuesday – which featured academy boss Per Mertesacker and CEO Vinai Venkatesham – was capped at 10,000.
Wilshere wants more for the final.
‘I watched the Youth Cup final last year and there was 60,000. And I know that our fans are better than Man United fans,’ he smiled.
‘Let’s build it. I watch the women’s games and that energy and that feeling, what the fans can create, is special. I want the players to experience that.’
He added: ‘It hasn't sunk in… it’s a special feeling and the final will be a very special occasion, one of the best in my life.’