A smile that shone and a love that faded: Rafael Leao’s seven-year AC Milan supernova
Be honest: when you saw Rafael Leao donning the red and yellow of Galatasaray for the first time, it just didn’t look right, did it?
We’d had some time to get used to the idea that Leao would be heading to the Turkish giants, and even longer to prepare for the notion that he would not be donning the red and black stripes this season, but it’s another thing entirely to actually see it.
Seven years of memories will do that. Countless ups and downs, glorious victories and painful losses, personal triumphs and traumas are woven into a story that stretches back into the previous decade. Whatever your opinion of Rafael Leao, you had one.
In many ways, Leao is the face of the modern era of Milan, and whether you think that’s right is up to you. Now that the story is over, though, we have the opportunity to reflect and a rollercoaster that never stopped producing adrenaline.
That boy with the smile
As so often happens in fairytales, it didn’t start in an ideal way. Having signed for a fee of around €30m plus add-ons from Lille, nobody really knew quite what to expect from the boy from Almada.
However, he came at a time when it felt like Milan were turning a corner, joining in the same window as the likes of Theo Hernandez, Ismael Bennacer and Rade Krunic, who were also relative unknowns but also went on to become pillars of the rebirth.
The issue at first is that Marco Giampaolo – the first head coach Leao worked under – didn’t seem entirely sure how to get the best out of the then-20-year-old. He had a rigid 4-3-1-2 system, and wasn’t convinced by the notion of using him as a starting striker nor as the attacking midfielder.
Then there was that moment. Milan had made an awful start to the season and trailed 3-0 at home against a Franck Ribery-inspired Fiorentina. There weren’t many fans left in the stadium, but those who stayed saw a moment of brilliant from the bright-eyed Leao.
He went on what would become a trademark jinking run through the left edge of the box, dropping three defenders en-route to a gorgeous finish. It would be just a consolation, and yet at the same time it was a lightning rod.
The first two crucial figures in Leao’s story came onto the scene that winter. The first was Stefano Pioli, who replaced Giampaolo after an ill-fated seven-game tenure, though Leao remained a bit of an in-and-out player under the new coach. That was until Zlatan Ibrahimovic returned for a second stint.
The pair have spoken at length about the instant brotherhood that was struck up on and off the field. Zlatan became an early mentor to Leao, who saw him as an older sibling, and when Pioli switched to playing two up front Rafa began to show his sparkle.
He would end that debut season with six goals in the league, which was only two less than his previous campaign with Lille. And yet, with Pioli understanding the talent he had at his disposal and with the team emerging from their shell, the conditions were being laid out for a lift-off.
The superstar is born
The Covid-19 period was not nice for anyone, given the immense amount of distress it caused so many people. Football had to go on pause when it would have probably been a welcome distraction, but it allowed Pioli and the Milan team to work away from prying eyes, creating a bond that would lead on to great fortune.
Milan played some electrifying football in the post-lockdown period, with the first indications coming in that aforementioned period towards the end of 2019-20, like the comeback from two goals down to beat Juventus 4-2 at San Siro.
Leao would score six Serie A goals in the 2020-21 campaign, one that would see Milan challenge for the title with city rivals Inter until spring before falling away. In the end, a win over Atalanta was needed on the final day to secure a return to the Champions League after a seven-year absence.
It wasn’t a trophy, but it felt like a first step forward, one that Leao played a big part in as the certified left wing starter. Oh, and he also became record-breaker: on 20 December 2020, he scored precisely 6.2 seconds after kick-off against Sassuolo, the fastest goal in Serie A history.
The campaign that followed almost deserves a separate piece, as Leao himself took a giant stride and put Milan on his shoulders. It was the definitive breakthrough year for the winger, one which led the Rossoneri to a 19th Scudetto and earned him the Serie A Most Valuable Player (MVP) award.
There were so many memorable moments within it, but it was during the final stretch that he created so many memories that will be cherished for a long time. In round 35, he scored a dramatic 82nd-minute winner against Fiorentina at San Siro after intercepting a goalkeeper clearance, keeping Milan ahead of their city rivals Inter.
The next round against Hellas Verona, he provided a fantastic assist for Sandro Tonali’s winner at the Bentegodi inside the final ten minutes after a surging run to the byline, again rescuing Pioli’s side from dropping what would have been fatal points.
The following week, in the penultimate game of the season, he latched onto a through ball and buried it between the goalkeeper’s legs to send San Siro into absolute pandemonium in the 2-0 victory over Atalanta. Theo Hernandez’s solo goal also stole the headlines, a demonstration of how important the left-sided ‘Theao’ duo had become.
It put Milan right on the precipice, and in the absolute most critical match of the season and arguably his career, Leao provided three assists in the first half – two for Olivier Giroud and one for Franck Kessie – to power Milan to a 3-0 victory, mathematically securing the title.
The celebrations that followed showed Leao in tears along with his father in the tunnel. He was too young for it to be a point of arrival, though it showed exactly what it meant to the player who dreamed of such moments when he was playing on the streets as a kid.
In terms of numbers, the former Lille man amassed 14 goals and 12 assists across all competitions, so it was a confirmation that he could become that reliable double-digit man, not just an occasional game-breaker and match-winner.
More was to come on a personal level in the next season too, as he upped the goal tally to 16. The brilliance grew too, like with the masterful brace early in the season in the 3-2 derby win over Inter. One was a strike of pure venom to make it 1-1, and the other a silky bit of skill to twizzle two men and finish to make it 3-1. The duality of Rafa, on display to the world.
Just weeks before the Champions League quarter-final clash, the winger was at the centre of a stunning 4-0 away victory against eventual champions Napoli in the league. He scored a brilliant brace against the runaway league-leaders, which laid down a marker for what was to come.
In the second leg at the Maradona, Leao produced what might have been his best assist in a red and black shirt. He picked up the ball in his own half, blew past Tanguy Ndombele, skipped around Giovanni Di Lorenzo, and left Amir Rrahmani on the floor before setting up Olivier Giroud for an open-goal tap-in.
Capping off his incredible season before the semi-final loss to Inter, Leao put transfer rumours to bed by signing a major contract extension until 2028, which included a €175m release clause. Right at the height of his powers, he made it clear that Milan was the only place he saw himself playing.
The slow decline
It was all going so well. Rafa was on the rise, his surfboard riding its highest wave, all with the new number 10 put on his back too. And yet, from here this isn’t a story that anyone connected with the Diavolo will recall with any pleasure.
There were still some great moments in 2023-24, like the off-balance overhead volley from a Davide Calabria cross at the Stadio Olimpico to secure a 2-1 win over Roma earlier in the season. There was a masterclass vs. PSG, when he again scored a bicycle kick to spark a 2-1 comeback victory in the Champions League.
Leao wrapped up the domestic season as one of the top assist providers in Italy, logging nine goals and nine assists in 34 league games. Milan dropped into the Europa League, where he racked up seven goal contributions in just six appearances before the loss to Roma.
The Stefano Pioli era would end after that campaign, with the final nail in the coffin being that European exit to a domestic rival in Daniele De Rossi’s Giallorossi. From there, Leao and the team entered the great unknown.
Paulo Fonseca arrived as the replacement to Pioli and there was hope that the proactive, possession-based style would help his compatriot shine again. Instead, the lasting image was the cooling break saga in the capital against Lazio.
Another countryman arrived midway through the season in Sergio Conceicao, and Rafael Alexandre da Conceição Leão would help his namesake secure a trophy after just a few days, providing the assist for Tammy Abraham’s winner in the Supercoppa Italiana final comeback versus Inter.
Leao would end that troubled season with 12 goals and 10 assists across all competitions, which was far from a bad return, especially when so many others struggled. Despite this, more serious questions were beginning to be asked about how much longer the Portuguese could go hand-in-hand with Milan.
Massimiliano Allegri became the fifth head coach that Rafael Leao would work under in the 2025-26 season, and there was an interesting tactical development: the shift to a front two, which he and Christian Pulisic were envisioned to spearhead.
It was a difficult campaign right from the first competitive game: a Coppa Italia win over Bari in which he opened the scoring with a header, before pulling up injured with a calf issue that forced a period on the sidelines.
Leao would amass 10 goals and three assists in 31 total appearances, but by his own admission he played through the pain barrier which limited his performance levels and his output. He developed pubalgia, which is something that takes some shaking off.
Ultimately it wasn’t a campaign for Milan to remember either (again). A late-season collapse saw a title fight with Inter turn into a scrap to stay above the dotted line and finish fourth. Defeat to Cagliari in the final round completed the capitulation, and it would turn out to be a sad curtain call for Leao too, at least in a competitive game.
The final wave
And so, we come to the end of the love story. If the cracks had been appearing prior, Leao provided what would prove to be the definitive earthquake just before the World Cup, revealing to Portuguese media his desire to move on.
“I think I’ve given Milan everything I could give. It’s been a club that helped me grow a lot, that supported me in the tough moments. And I’m happy to have managed to write my name in the club’s history,” he said.
“Everyone has their dreams, their challenges, the things they desire, the goals they want to reach. And I too want to try a new challenge in a new league.”
How did it come to this? What made the love run out? This is where the reflections on Leao’s time at Milan can become complicated and even a little bit uncomfortable, because the idea that there is ‘blame’ to dish around it a controversial starting point.
However, it is safe to state that many hoped and many believed Rafael Leao was capable of reaching the very top. That 20-goal-per-year marker was regularly dangled in front of him as the next hurdle to jump over, but sadly it would remain a distant mirage.
Once of the biggest criticisms levelled at the ex-Sporting starlet is that he never reached the level of consistency that would cause him to be considered a complete player. He would drift in and out of games, he would be up and down during seasons, and the obvious talent he has made that a shame.
There were also discussions had about the aspects of his game that were perhaps not strengths, more specifically the dilemma of whether building/engineering a system or a tactical identity around a single player because of a lack of defensive work rate was sustainable or correct. Everyone will have their own opinions on that, which is the beauty of football.
It doesn’t feel right to end this retelling of the story the way that it actually ended though. After a summer of mystery regarding where he would end up – if anywhere at all – a new adventure in Istanbul now awaits. But not without a few tears first.
After the game against Venezia on Friday night at San Siro, Leao somewhat surprisingly appeared in front of the Sky cameras to give his final goodbye to the Italian media and to the fans watching.
“I said goodbye to my team-mates after seven years with them. The club has always supported me, helped me grow, and made me understand what high standards mean, representing a great club like AC Milan,” he said.
“The time has come to say goodbye. I would have liked to say goodbye in a different way, I would have liked to say goodbye in a better way, perhaps by being there on the pitch one more time in front of the fans, who helped me so much, especially during the tough times.
“I will definitely be part of the club’s history, because I know what I did here. I will carry in my heart all those who helped me, I just have to say thank you. […] I cried, a lot, it’s normal, the emotion is normal.”
Leao was a supernova. He exploded in a flash, shone brighter than everyone and everything around him, but the shine eventually fizzled out. The fuel run out, and now a void remains, the magnitude of which we will only see when the dust settles.
Whether you loved him for all his flaws or you were irritated deeply by them, Milan are saying goodbye to a maverick. In many ways, the game itself is losing those who play like Leao does, the spontaneous geniuses that decide a match when they want to.
So often he would stroll around, watching events elsewhere on the pitch, and then at the click of a finger burst into life, tearing down the wing on a run that left him smiling and the defenders wide-eyed with fear.
It had been a while since the Rossoneri had someone like that, and it could be a while until another comes along. It’ll feel strange for a bit, it might even sting, but Milan will move on and Rafael Leao will move on. The legacy? A beautiful chapter we should all never be ashamed to revisit.
