Real Madrid already knew the player well, but it was that double-header against Bayern Munich that turned the club's attention into something more concrete, with the France international's performances at the Bernabeu drawing focus from across the club's hierarchy.
The interest has only intensified since. Every time the typically reserved winger produces another standout display, the conviction within Real Madrid grows that he is the player they want, given how consistently he has continued to raise his own ceiling.
Real Madrid's presidential election campaign earlier this year acted as a brake on several transfer matters, but it also reawakened an instinct that had lain somewhat dormant at the club — the search for a new defining attacking reference point. That is the status Olise now holds in the eyes of those running Real Madrid's recruitment.
As a result, the club is working toward a deal that currently appears close to impossible. But examples of similarly ambitious pursuits exist throughout Real Madrid's history over the past 25 years.
During the campaign, senior Real Madrid executives made approaches that left the door open to a future deal, according to reports. Olise was understood to be the club's primary attacking target even then, with informal contact made during the election period in search of common ground.
Those early conversations laid the groundwork for negotiations with a Bayern Munich side that continues to resist, though the German club is aware the situation could become considerably more difficult should the player ultimately give his definitive agreement to join Real Madrid.
With the election won, club president Florentino Perez moved to fulfil a campaign pledge by lodging an official €150m offer for a player considered one of world football's elite performers. That move came for Julian Alvarez, with the bid given a level of formal public visibility rarely seen for an offer that was ultimately rejected — evidence, in the eyes of Real Madrid's hierarchy, that campaign promises were not empty words, and that Perez's mandate, which runs until 2030, carries genuine intent.
Real Madrid continue working to complete a deal for the player considered to have had the single biggest individual impact in world football over the past year. Bayern Munich, a club known for resisting the sale of its leading figures but one that ultimately tends to accept market realities, continue trying to dissuade any interested party.
The message from Munich has not changed publicly — Olise is not for sale — but the decision now effectively rests with the player himself. Should that point be reached, sources in Germany suggest Bayern would be prepared to set a new transfer record for an outgoing sale, surpassing the €222m Paris Saint-Germain paid for Neymar.
It is that same Parisian club, formerly home to Neymar, that represents Real Madrid's most significant rival for Olise's signature. Given the working relationship between the two clubs, however, sources suggest there will be no real confrontation — whichever side does not land the player is expected to step aside for negotiations with Bayern Munich, a club Real Madrid have always sought to treat with maximum respect and cordiality, something rarely straightforward in situations of this kind.