Of all the vivid imagery from Tottenham Hotspur’s Europa League triumph, the one picture that sticks the most in Nick Montgomery’s mind is not the trophy lift, the confetti-streaked chaos inside the San Mamés Stadium in Bilbao, the post-match party or the parade through North London past 250,000 ecstatic fans hanging off trees, lampposts and traffic lights.

It was Steve Dukes – the club’s kit man for the past 20 years – swinging his jacket above his head, hollering with joy like a bloke who’d just been set free from jail.

In a way, thanks to their first trophy since 2008 and first European success in more than four decades, he had been.

“Kitman Dukesy” has become something of a morning companion for Montgomery, brought to the club this season by Ange Postecoglou. Montgomery would try to get into work at Hotspur Way nice and early to beat the traffic, and part of his routine was to slip into the club sauna, usually alongside fellow assistant Mile Jedinak.

More often than not, he’d find Dukes already there, reflecting on the past two decades of nearlys and not-quites. Having started at the club as a steward in 1987, he had seen too much heartache to simply accept the bold assurances from the coaching staff that better days were ahead.

“I kept saying to him, ‘Look, we’re going to win, mate. Relax,’” Montgomery said.

“You’d see the angst and anxiety on him because he’s just not used to it. The club had failed so many times in big games. And I just remember after the final whistle him swinging his jacket around, jumping up and down. I was celebrating with Ange and a couple of the other coaches, and then I just looked around and ... it was just wild scenes.

“The players were just buzzing because even if they’d just joined the club, they’d been hearing that Spurs never win anything, Spursy ... all these things, and it’s like you’ve just ended many years of hurt, of the fans getting smashed and the club getting smashed for never winning anything.”

Montgomery is still coming to terms with the magnitude of what he has helped Spurs achieve this season. Sacked by Hibernian in May last year, after eight months as head coach of the Scottish Premiership side, he had other opportunities to continue as a manager – but couldn’t turn down the chance to work with Postecoglou, who was one of the first to send Montgomery a congratulatory message after he steered the Central Coast Mariners to an emphatic A-League grand final victory in 2023.

The departure of previous assistant Chris Davies to Birmingham City opened up a spot on Postecoglou’s staff for Montgomery, who was joined at Spurs by his own long-time lieutenant Sergio Raimundo.

Part of Montgomery’s portfolio was to look after Tottenham’s set pieces, in attack and defence, in tandem with Jedinak, another ex-Mariners legend. But Postecoglou’s collaborative approach with his assistants gave him broader scope in terms of adjusting the team’s game model and structuring their training sessions, all of which were meticulously planned and reviewed afterwards.

It was never easy, though, due to one of the worst injury crises a Premier League side has ever seen, and the incessant noise from the outside questioning everything Postecoglou and his staff were doing.

“It’s been a great learning,” Montgomery said. “It’s also been an opportunity for me to grow and support Ange in what was a difficult season, but in the end, an amazing season.

“The media tried to make out that the team never changed the way it played and just never adapted, but that’s completely not true. It’s difficult to fully adapt when you’re making five, six changes every week, we had so many injuries, you know, you’ve got young players that are just coming in experiencing that level for the first time ... we never abandoned our principles all season.

“We always believed that we could go on and win the Europa League. The players believed in Ange and backed him, even throughout the really difficult times and I think that’s a real test of a top world-class manager.”

The celebrations, though? An utter madness, and Montgomery was in the thick of it. One of many viral videos from the post-match in Bilbao caught James Maddison leading the players in a chant in his honour, to the tune of Freed From Desire: ‘Monty’s on fire, your defence is terrified!’

“The boys were in full force, mate,” he laughed.

“James Maddison, he reminds me a lot of Jason Cummings – that sort of character. He’s just a majestic player, a wonderful player, a football brain. Some of the stuff he does, the game he stands still when he gets on the ball, and he just sees things that other players don’t see but not only that, he’s just a great guy, a proper character. He was trying to get me up on the stage!

“I was always banging on him about taking corners and free kicks and getting him out there to do extra practice and stuff, and you see his stats in terms of the assists that he got through the season, considering he had a couple of injuries as well … he’s actually up there in terms of the Premier League’s top scorers from free kicks and assists.”

Though he only moved to Australia when the Mariners signed him as a player in 2012, Montgomery has become an Australian citizen and appreciates the significance of what Postecoglou is doing for Aussie coaches and the game back home more broadly.

The A-League might feel a million light years away from the Premier League, but it is never far from their field of vision. Literally.

“We always watch the A-League,” he said. “Obviously, the timing of the A-League [in the UK], it’s normally when we’re having a coffee in the morning, preparing a session, going through all the sort of pre-training stuff. We’ve always got the A-League on in the coach’s office; Ange has all the football on in his office, all the time. We’re just immersed in it.

“We try to be real advocates for the A-League, because we know the quality of the players that are in there, and a lot of good young players coming through now. I’m really proud of the fact that we played a part in maybe more coaches now believing in young players and helping to develop them ... that’s a great thing to see.”

Like Postecoglou and the rest of Tottenham’s coaching staff, Montgomery is currently in a state of limbo, waiting for news from above as to whether a managerial change will be made - as has been widely forecast in the English media.

However, the Europa League win has changed the atmosphere, and with Postecoglou enjoying the clear backing of the entire dressing room – and, once again, the majority of Spurs fans - moving him on would be an enormous risk.

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“I came here for one year already, and it’s been an amazing journey,” Montgomery said.

“I’ve learned plenty – it’s probably hard for me to say one thing, but I learned that, yeah, I can coach in the Premier League with World Cup-winners and world-class players.

“In future, I’ll definitely be looking to get back into management. That’s what I spoke about with Ange in our first meeting. But for now, until we’re told otherwise, I’m really looking forward to coaching in the UEFA Champions League next season and continuing to support Ange.”