Santiago Gimenez's Journey at Milan: From Struggles to World Cup Aspirations

Santiago Gimenez arrived at San Siro as if fired out of a cannon.

The numbers from Feyenoord were not those of a prospect, but of a finished article: 65 goals in 105 games, back-to-back seasons beyond the 20-goal mark at De Kuip, a penalty-box predator who had bullied Eredivisie defences and drawn a queue of suitors from across Europe. Premier League clubs circled. Milan won the race, helped by the most old-fashioned of tiebreakers – the heart. Gimenez had grown up a Rossoneri fan and chose the club he had watched on television as a child.

On paper, it looked perfect. On grass, far less so.

He managed six goals after landing in Lombardy in February 2025, a modest return that never quite matched the weight of expectation. The explanation at first felt simple enough: new league, new language, a different rhythm of football. Strikers live on instinct, but they also live on familiarity. Gimenez had stepped out of his comfort zone and into a club that was already wobbling.

Then came the real blow. His first full season in Italy was shredded by injury. Five months gone. Five months without rhythm, without sharpness, without that weekly dialogue with the goal that defines a No. 9. When he did return, he looked like a man trying to sprint through sand. The season closed with just a single Coppa Italia goal to his name.

At a club like Milan, that kind of line on the stat sheet brings questions. And this summer, the questions are everywhere.

Massimiliano Allegri is on his way out, another reset is under way, and the spotlight has swung onto several senior names. Gimenez, still under contract until 2029, sits right in the middle of that debate. Is he a future pillar of the project, or a saleable asset in a squad shake-up?

One of the men watching most closely is Jared Borgetti, Mexico’s second-highest scorer of all time and a striker who knows what it means to carry the expectations of a country. Speaking to GOAL on behalf of 10bet, Borgetti did not sugarcoat the situation.

“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,” he said. “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.”

It is a blunt assessment, but not an unfair one. Gimenez is not the kind of forward who manufactures games on his own from the touchline. He is a finisher, a penalty-box specialist who feeds off movement around him and a system built to funnel chances into the area he patrols.

“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,” Borgetti added. “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.”

The atmosphere around Milan has been tense. On the pitch, performances stuttered. Off it, the club prepared for another change in the dugout. Yet inside that storm, Gimenez has found one constant: the crowd.

The Mexican has not hidden. He has spoken openly about what the move means to him and about the bond he feels with the stands at San Siro. In an interview with Billboard Italia, he laid it out plainly.

“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 said. “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 word matters. Family. It hints at why, despite the whispers about a transfer, Gimenez remains convinced he can still write a different story in red and black. It also hints at why the Curva Sud has not yet turned on him with the ferocity it has reserved for others. They see the effort. They know the context. They also know something else: the next few weeks could change everything.

Because while Milan reset, Gimenez steps onto the biggest stage of all.

The 2026 World Cup lands in Mexico, and with it comes a responsibility that dwarfs any club crisis. Gimenez is expected to lead the line for El Tri in a tournament that will start in the most symbolic way possible: the opening match at the Azteca, against South Africa, on a Thursday that will freeze a nation in front of its screens.

“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,” Gimenez said of the tournament. “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 promise, the sort of line that will be replayed endlessly if he delivers – or thrown back at him if he does not. Yet it also reveals the core of his mindset. This is not a player cowed by a difficult club season. This is a striker who still sees himself as the man for the moment.

Mexico’s path out of Group A will run from that opener against South Africa to clashes with South Korea and Czechia. On paper, it is a group that offers opportunity as much as danger. For Gimenez, it offers something more: a runway.

A flurry of goals on home soil, a deep run into the knockout rounds, and he will not just return to Milan with a medal haul and a highlight reel. He will return with rhythm, with confidence, with the feeling he last had in Rotterdam when every touch in the box seemed to bend towards the net.

By then, Milan’s new coach will be in place, the squad reshaped, the tactical board wiped clean. The club must decide whether to build a system that finally plays to the strengths of the Mexican they fought so hard to sign, or to cash in on a forward whose value could spike with every World Cup goal.

Gimenez has made his stance clear. He wants to stay. He wants to prove that the boyhood dream can still become a career-defining chapter, not a cautionary tale.

The next chapter, though, will be written in green, white and red, not in red and black. And if he does walk back into San Siro as the man who lit up a World Cup on Mexican soil, how many doubters will still be left to silence?