Santiago Gimenez: From Dream Move to Struggles at Milan

Santiago Gimenez arrived at San Siro with the numbers of a fantasy signing and the heart of a lifelong fan. The reality has been far harsher.

At Feyenoord, he was a machine. Sixty-five goals in 105 games, back-to-back seasons beyond the 20-goal mark, a penalty-box predator who turned De Kuip into his own stage. Europe noticed. Premier League clubs circled. Offers came, and were pushed aside.

He chose Milan. Not for the money, not for the league, but for the shirt he had loved since childhood.

From dream move to difficult awakening

On paper, the move looked perfect. A prolific No. 9 stepping into one of Europe’s great cathedrals, a club searching for a reference point in attack, a fan base that still worships its great centre-forwards.

He started reasonably. Six goals after landing in February 2025 hinted at a smooth transition. The talk was of “teething problems”, the usual settling-in period when a striker swaps familiar streets for a new language, a new league, a new pressure.

Then his body turned on him.

In his first full season in Italy, injury cut him down and kept him there. Five months on the sidelines for a player who lives on rhythm and repetition is an eternity. Match sharpness vanished, confidence frayed. When he did return, the goals did not follow. Across the whole campaign, he found the net just once, in the Coppa Italia.

For a club like Milan, that sort of return invites questions. About the player. About the team. About what comes next.

A striker caught in a struggling side

Jared Borgetti knows exactly what it means to carry the hopes of Mexico in Europe. The country’s second-highest scorer has watched Gimenez’s Milan story unfold from a distance and sees more than a simple flop.

“Unfortunately, the move to Italy hasn't been a good year for Santiago, but it's not solely due to the player or his problems,” Borgetti told GOAL, speaking on behalf of 10bet. “I think his injury has also played a significant role in preventing him from achieving consistency, competing for a starting position, and reaching the level he showed in the Netherlands.”

Then he widened the lens.

“I believe Milan as a whole hasn't been performing well, and when a team isn't playing well, no player can truly stand out. To say that any player stood out at Milan this season, I think we'd be exaggerating or just saying it for the sake of it, so, I don't think the team helped much either.

“He's a player who needs the team to be playing well, for the system of play to suit his style, so that he can have scoring opportunities and create plenty of chances for the team to capitalise on. I do think the dip in form is partly due to him, partly due to the team, and obviously, the atmosphere also ends up affecting his individual performances.”

That atmosphere is changing again. Massimiliano Allegri is on his way out, another reset is underway, and several senior names find their futures under scrutiny. Gimenez is among them. A move has been floated. A fresh start elsewhere whispered into the conversation.

“Like a family”: the bond that keeps him in Milan

Through all of it, Gimenez has clung to one thing: the club he grew up admiring.

“I have supported Milan since I was a child, so finding myself playing in that stadium that I could only see on television means a great deal to me,” he told Billboard Italia. “The fans welcomed me with so much affection and, despite the fact I have not yet performed as I would have liked, they continue to push me and trust me. Like a family.”

That detail matters. The Curva Sud can be unforgiving, yet it has not turned on him with the ferocity others have felt. There is still patience, still a sense that this story is not finished.

His contract runs until the summer of 2029. Milan must decide whether to build around him in the new cycle or cut their losses. Gimenez, for his part, wants to fight for the version of himself that terrorised Dutch defences.

He might find that version back home first.

World Cup stage, home soil, huge promise

If there is a stage built for redemption, it is a World Cup in your own country.

Mexico will open the 2026 tournament at the Azteca, facing South Africa on a Thursday night that will grip a nation. Gimenez is expected to lead the line, to carry the weight of a jersey he already understands too well.

“When you wear the national team jersey, you represent an entire country, so you have a huge responsibility, but at the same time, it’s a wonderful thing,” he said of the prospect. “I know that Mexico, with its people, is very strong at home. I’m convinced it will be a great World Cup. Mexico will win, and I’ll be the top scorer!”

It is a bold claim, the kind that can sound naive or fearless depending on the outcome. But it reveals a striker who has not lost his self-belief, even as his club season unravelled.

After South Africa, El Tri will meet South Korea and Czechia in Group A. The mission is clear: ride the emotion, reach the knockouts, and let Gimenez find his scoring touch under the roar of a home crowd.

If he does, he will not just return to Milan with a medal tally or a Golden Boot dream. He will come back with something more valuable to a No. 9 than any tactical tweak or new coach.

He will come back with goals in his boots, noise in his ears, and a point to prove in the stadium he once only saw on television. And if that version of Santiago Gimenez walks back into San Siro, who really wants to be the one to bet against him then?