A fee in excess of £20m might seem like a gamble for an uncapped 21-year-old who has never played top-flight football, but gamble is not the word that springs to mind when assessing Maddison. His rise to the Premier League has seemed inevitable since long before he made his debut for Coventry City at the age of 17. Even as a boy he was a prodigious talent.
Richard Stevens has seen many hopefuls pass through the doors of the Alan Higgs Centre during his 11 years with the Sky Blues. As head of the club's academy, he takes great pride in the fact that Coventry have produced no fewer than 44 first-team players in that time. But he also makes no secret of the fact that Maddison was a bit different to the rest.
Maddison to join Leicester
James Maddison has chosen to join Leicester City over Southampton, according to Sky sources.
"Anyone would have spotted him," Stevens tells Sky Sports. "The opposition always did. I remember even when James was 15 and we used to go and play against Nottingham Forest, it would always be the first thing that they would ask me. 'Is he playing?' They were not the only ones. Everyone remembered James and they always spoke about him."
Back then, Maddison's dream was to play for the club that he had supported since he was a small child. As local as they come, he attended Richard Lee Primary School - literally up the road from Coventry's training ground - and lived just around the corner. Youth coaches are well accustomed to helping youngsters to mature but with Maddison there was little need.
"In the nine years that he was here with us, he was never a minute's problem," Stevens said. "There was never a behavioural issue and there was never a need for us to get him to work harder. He was a boy who just loved football. Nothing else mattered. Because of that, everything that has happened to him, you could foresee way back then."
It was the technique and the vision, the speed of thought and control. Unusually for a young player, it was the decision-making too. "He was always looking to make things happen but was never afraid to uncomplicated the game and play simple at the right times either," added his old coach. "He was the one who would do more and ignite games."
Maddison's first season in the first team ended with a last-minute winner against Crawley in the final game. His second season was marked by his sale to Norwich City with just hours of the winter transfer window remaining. Even though he was loaned back to Coventry for the rest of the campaign, fans were frustrated. Finances dictated the decision.
Speaking to then chief executive Chris Anderson at the time, it was clearly not an easy call. "I love James Maddison as much as the next fan so that was a decision fraught with emotion for the football club and one we thought long and hard about," he told Sky Sports. "I had it at home too." Even Anderson's son urged him not to sell the club's star midfielder.
It was a pity because Maddison was improving rapidly, learning on the field and off it. The coaching staff have fond memories of the bond that he quickly forged with former England midfielder Joe Cole during their time together. The youngster was eager to pick the brain of his experienced team-mate, anxious to pick up anything that he could.
There were times in the following season when Maddison himself might have wondered whether a mistake had been made in joining Norwich. The Championship was supposed to be the next natural step but instead he was loaned to Aberdeen. He returned in the January determined to earn a place in the Canaries side but Alex Neil made him wait for his chance.
The appointment of Daniel Farke at Carrow Road last summer was the catalyst for change. Belatedly entrusted with a key role in the team, Maddison shone just as so many had predicted. He soon emerged as the outstanding attacking midfielder in the Championship, creating more chances than anyone else in the competition last season.
"Every time I blink I see that he has got another man of the match award or another player of the month award," Stevens said with a smile. "That is what drives James, that feeling that he is the one who can capture the imagination of the fans. If you look at the Norwich players, they all look like they adore him. That is what he creates."
It will be more difficult to achieve that status at Leicester. It could take time for Maddison to establish himself as the creative hub with so many experienced Premier League players around him. But history would suggest that when presented with a barrier to his progress, this is a player who has the application and the ability to overcome it eventually.
"This next move will challenge him I am sure," Stevens said of Maddison's expected move to the King Power Stadium. "He is going into a team in the top half of the Premier League and that will be a big test for him because he will be around some pretty high class players. But whenever James has been pushed, he has found a way of adapting to it.
Inside Coventry's academy
Adam Bate went to visit academy manager Richard Stevens to find out how the club has managed to produce so many first-team players against a backdrop of uncertainty.
"When he was a 16-year-old he adapted to playing for the under-18s. When he was an 18-year-old he adapted to playing for the seniors here at Coventry. He went to Aberdeen and he adapted. He went to Norwich and he adapted. He went to play for the England U21s and he got man of the match on his debut. He just has this ability to take the next step."
Whatever happens, Maddison won't forget his roots. The Coventry connection is still strong. "He's been a shining light for this academy and we all keep in touch with him," Stevens added. "He came back recently and sat with the under-15s. It was not planned but they were around so he chatted to them for half an hour. All he wants to talk about is football."
It remains to be seen whether Maddison can justify the fee and continue his anticipated progress. But Leicester have not only acquired the services of a player who was among the best performers in the Championship last season, they have clearly got someone who has the appetite to achieve so much more. Maddison's rise is not over yet.
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