Welcome to the biggest season of James Maddison’s career

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On the opening weekend of a new season, everyone starts again from scratch. Every player has a blank sheet of paper in front of them and the autonomy to write whatever they want on it. In nine months, they could be looking back on the best work of their career.

And no player will be more keen to start writing a new story for himself than James Maddison when Tottenham Hotspur start their season at his old club Leicester City on Monday night. Not necessarily because he is going back to the ground where he spent five seasons, but because last season for Maddison was so exciting, so promising, so frustrating and so painful, almost every possible emotion squeezed in between August and June.

Remember the Maddison of last August, September and October, back when he walked into Tottenham and immediately started playing like he had been there for years. That late summer of 2023, Maddison was special: perfect for Ange Postecoglou, perfect for Spurs. Everything went through him and he assumed the roles of creative leader, vice-captain and No 10 shirt with remarkable ease. No learning curve required. More than any other player, he encapsulated the thrill of the new era.

But the honeymoon period did not last. In November, Maddison injured his deltoid ligament and missed almost three months. It was the worst injury of his career, made all the more painful for coming in only his 12th game for his new club, when he was in the form of life. Maddison was completely crestfallen.

It was not easy for Maddison to do his rehab while watching his team-mates playing without him but he worked hard and went to Dubai for warm-weather rehabilitation with club medical staff in December. By the end of January, he was back in the team. There was still just under half of the season left to come — plenty of time for Maddison to get back to his initial form and for Spurs to finish in the Champions League spots.

What was so frustrating was that in the second half of the season, Maddison never quite got fully back to his best. There were glimpses: a clever assist for Cristian Romero in the 3-1 win over Crystal Palace in March, a run into the box to convert Pape Matar Sarr’s cross when Spurs won 4-0 at Villa Park later that month. It felt as if Maddison was back and so were Spurs, and that fourth place and Champions League qualification were well within reach. But that is not how the end of the season went.

Spurs and Maddison struggled for rhythm in the spring. Maddison was so important to Spurs that the whole team suffered when he was not at his best. After painful defeats to Newcastle United and Arsenal in April, Postecoglou made a decision that would have been inconceivable at the start of the season. He dropped Maddison for the trips to Stamford Bridge and Anfield.

Maddison came back into the team for the last three games but Spurs had already lost too much ground on Aston Villa in the race for fourth. And Maddison’s struggles would lead to him paying a painful price at the end of the season. He had finally forced his way into Gareth Southgate’s England team in 2023, having gone to the Qatar World Cup but not playing a minute after failing to shake off an injury. He was playing more, starting the Euro 2024 qualifier against Ukraine in September and the friendly against Australia in October. It felt for the first time as if Southgate could count on him. And even after his struggles, Southgate picked Maddison in his 33-man extended squad for the Euros. Maddison came off the bench for the warm-up game against Bosnia and Herzegovina at St James’ Park.

But three days later, Southgate had to cut seven from his squad to take to Germany, and Maddison did not make the plane. “Devastated doesn’t quite cut it,” Maddison wrote on social media. “My form for Spurs when coming back from injury in the second half of the season probably wasn’t at the levels I had set, which gave Gareth a decision to make.”

It was remarkable that a season that started with Maddison playing so well should end so painfully. In those first few months, he had the world at his feet, making the step up from Leicester to a ‘Big Six’ club look like child’s play.

For Maddison’s whole career, he had been spoken of as being one of the most talented English players of his generation. Ever since he was playing for Coventry City, all of the big clubs knew about him. Barcelona scouts came to watch him for Norwich City at Carrow Road. And in those first few weeks at Spurs, it felt like Maddison was fulfilling that potential and becoming the player he was always meant to be.

But after the way his season went, it feels like Maddison has to do the hard work all over again. He is still a first-choice player but there may be more competition for that left central midfield spot this season. Dejan Kulusevski is as much of a midfielder as he is a winger for Postecoglou’s Spurs now, and then there is the brilliant 18-year-old Lucas Bergvall, who has just arrived. If he shines — possibly at first in the Europa League — there will be calls for Bergvall to play more often. And then there is still the chance Spurs add another central midfielder in the last two weeks of the window, having tried to sign Jacob Ramsey in June.

But there are reasons to be optimistic, too. We know how good Maddison can be in this system, how much he wants the ball, how good he is at finding those pockets of space and playing those clever little passes of his through to Son Heung-min. The arrival of Dominic Solanke, a close friend of Maddison, will give him a new target man to work with and could lift the whole team. We know Maddison can also hurt teams from set pieces and from the edge of the box. We all saw just how good Maddison can be for Spurs, the man who makes the whole thing work. The challenge for Maddison — and Tottenham — is to turn the start of the last season into the whole of this one.

(Top photo: Andrew Milligan/PA Images via Getty Images)