But now, holding court in this East End pub, Maddison, an emotional character by his own admission, needs a moment to gather his words to truly sum up the pain of being relegated.
‘I was absolutely devastated,’ he said. ‘You get to the point where you realise relegation means people lose jobs; leaving the Premier League to go to the Championship the club obviously lose a lot of money and people lose jobs, fewer people work at the training ground, stuff like that.
‘And when you think about it like that, and it’s obviously down to players on the pitch, it can hit home. That’s the type of person I am, a quite emotional person, and it did hit me and it was hard.
James Maddison is relishing the chance to play for Tottenham in the Premier League following his £45million summer move from relegated Leicester
Maddison was left ‘devastated’ after Leicester suffered relegation on the final day in May
‘But you’ve got to dust yourself down and look forward and when opportunities like this come calling it’s not one you can say no to.
‘So onwards and upwards, blinkers on, the hunger’s back and the motivation to go and do well and prove to everyone why I’ve signed for the club.’
Maddison is 26 now, no longer the rising star that Tottenham kept tabs on when he was at Coventry City and Norwich. He arrives in north London to be the main creative midfielder.
Nine Premier League assists last season bettered anyone in Tottenham’s squad — Ivan Perisic was Spurs’ top assist maker with eight — and the onus is on Maddison to deliver straight away, starting at Brentford on Sunday.
‘I’ve always had a strong self-belief and I’ll always back myself and my own ability to succeed,’ he said. ‘It hasn’t failed me so far so I will continue to have that mindset and attitude.’
It is put to Maddison that he looks and feels like a Tottenham player: a footballer in that familiar attacking midfielder role that Christian Eriksen and Dele Alli both thrived in at Tottenham in recent years.
Mention of Eriksen earns a wry smile from Maddison for here is a player he spent his teenage years and youth-team years studying closely.
At his Tottenham peak Eriksen was considered one of the most effective creative midfielders in Europe. For Maddison, it was one of the wells of inspiration he would draw from to pave his own way to the top.
New Spurs manager Ange Postecoglou will expect Maddison to be a primary creative force
Spurs will have to cope without Maddison’s England team-mate Harry Kane after the striker sealed his move to Bayern Munich last week
‘Christian was a brilliant player. I used to watch Christian when I was a little bit younger, making my way in the game and he was at the top of his game in the Premier League,’ said Maddison, speaking at the TNT Sports start-of-season event in London.
‘As my career developed and he was still at Tottenham, playing against him, swapping shirts with him, telling him what I thought of him as a player, and him being such a nice guy in response to that, he was definitely someone I looked at, especially when I was in that teenage phase of watching players in my position at the top of their game. He was one I looked up to, yes.’
Newcastle made no secret of their desire to bring in Maddison this summer and with Eddie Howe’s side offering Champions League football — something Tottenham don’t have to offer him — there were many scratching their heads.
But Maddison is a believer in destiny and the vision of ending up at Spurs has been etched on his mind for years. ‘I definitely do to be honest,’ he says, asked if he thinks he’s a ‘perfect’ fit for Tottenham as a club.
‘In the summer when I was speaking to my agent about moving clubs and you come to a place where you need to make decisions and where you want to go and what you think fits best, I could actually see myself playing for Spurs.
Maddison studied Christian Eriksen’s style of football when developing his own game
‘There’s a little window for me at Tottenham Hotspur, a creative player that they’ve always had, but maybe not had in recent years.
‘I could definitely see myself, when making the decision, playing for Tottenham in that kit, in that stadium and being the creative player I know I can be.’
Postecoglou will want — and need — more from Maddison, however, given he scored just once in his final 14 league games for Leicester as they were caught sleepwalking to the Championship.
So, with his 27th birthday on the horizon in November, are his greatest days still ahead of him?
‘Nah, I peaked two years ago!’ Maddison says, immediately bursting out laughing.
‘We’ve had a few pre-season games so far and it’s all about learning. Not just for me but for all the players, just learning how [Postecoglou] wants each role to play.
Maddison (left) with new Tottenham captain Son Heung-min (centre) and Sergio Romero
‘There’s that more advanced midfield role, a No 8 if you want to call it that, and to play between the lines and do what got me to this position now.
‘The way I play won’t change, that’s how I am, that’s my nature, that’s me as a footballer and him and the club obviously like that, which is why they brought me in.
‘So [the aim is] to be that goalscoring, creative midfielder and that isn’t an easy job, so I’ll keep working and hopefully I can be successful.’
Destiny? Maybe. But only time will tell if Tottenham finally have the Christian Eriksen successor they have spent years searching for.
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