‘We believed all season': Inside Tottenham's euphoric Europa League victory
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.'
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