He was seven years old, being taken by his family for a trial at Chelsea. A reluctant Olise issued terms to his loved ones: he would go only if he could wear his Manchester United shirt. He wore it.
That streak of independence — a refusal to be managed, a determination to do things his own way — followed him through every academy door he walked through, and eventually out of two of England's biggest clubs before he had even turned 15.
Olise made his World Cup breakthrough this week, playing a starring role as France's creative hub in their 3-1 victory over Senegal. His pass set up Kylian Mbappe's opening goal, and he drew saves from Edouard Mendy as France turned a flat first half into a dominant second. It prompted those who watched his academy years to ask: how did Chelsea and Manchester City let him go?
The honest answer is that they did not so much let him go as push him out.
Olise spent seven years in Chelsea's academy, where his talent was never in doubt. His teammates at St George's Park returned to their rooms one evening to find their beds soaked. Olise had somehow got hold of everyone's keys and poured water through every door. He was the kind of kid who played keepy-ups at the halfway line when a coach told him to join the group, then simply booted the ball away and walked inside instead.
Chelsea tolerated it because of what he could do with a football. Parents of his teammates were sometimes surprised by what he was allowed to get away with, though those who know him describe it as the behaviour of a spirited teenager rather than anything more serious. He was well-liked by his peers. The mischief was the expression of someone who had never needed the structure as much as the others did.
The club held on until he was 14 before deciding enough was enough. He trialled at Manchester City and was taken on, but lasted only three or four weeks at the academy in a spell sources describe as cut short by further misbehaviour. Some who were close to him at the time believe he was simply rebelling against being in a new school in a new city, far from the friends he had grown up with.
A trial at Reading followed, and from that point the story turns. Olise passed the trial on ability alone and joined Reading's scholarship programme in 2018, making his first-team debut the following March. He matured noticeably in Berkshire, though a leaked Instagram direct message in which he told a girl he was "on bigger things" and wouldn't be playing for "a small Championship team for too long" gave a glimpse of both his confidence and his lack of filter. It was not entirely wrong.
Crystal Palace paid £8m for him in 2021, doing their own due diligence on the attitude questions first. By then, those questions had largely been answered by what he was producing on the pitch. Chelsea came back for him in June 2024, their former academy star's rebellion long since forgiven, but were priced out of a move and unwilling to break their wage structure. He went to Bayern Munich instead.
Now he is playing as one of the best wingers at this World Cup, setting up Mbappe to equal and then surpass Olivier Giroud's all-time France scoring record on his way to 58 international goals, running the Senegal defence ragged from the first minute of the second half.
Chelsea and Manchester City's loss. France's gain.