‘The Boy Took His Time’ – Why New AC Milan Contract for USMNT Star Christian Pulisic Remains Unsigned
Christian Pulisic may have lit up the San Siro with his most productive season to date, but as the summer sun beats down on Milan, one big question still hangs in the air—why hasn’t the American star signed his new contract?
It’s been months since reports first surfaced that a fresh deal was on the table. Everything seemed lined up. The details were discussed, the terms seemingly agreed. And yet… nothing. No signature. No press release. No celebratory photos with pen in hand. Just silence.
AC Milan and Christian Pulisic: A Match That Just Works
Serie A – Udinese v AC Milan
Let’s be honest—Christian Pulisic has been a revelation for AC Milan. When he arrived from Chelsea in the summer of 2023, many wondered whether the American winger could reignite a career that had stalled amid injuries and squad rotations in the Premier League. Fast forward to the end of the 2024-25 campaign, and those doubts have been firmly laid to rest.
Seventeen goals across all competitions. A talismanic presence. A renewed sense of confidence. Christian Pulisic didn’t just find form—he found a footballing home. In a Milan side that often struggled for consistency, especially after missing out on European qualification, it was Christian Pulisic who frequently dragged the Rossoneri forward.
The Agreement That Was… Then Wasn’t
By mid-season, it looked like the marriage between Christian Pulisic and Milan was set to continue long into the future. Reports circulated that a contract extension had been agreed—one that would add an extra year to his current deal, keeping him at the club until at least 2028. Fans breathed a sigh of relief. The media moved on.
Except, the deal was never made official.
Sources close to the club insisted everything had been discussed, down to the smallest details. So why the delay? Why the radio silence?
‘The Boy Took His Time’ – Asking the Right Questions
According to respected Italian journalist Matteo Moretto, it wasn’t a case of cold feet or behind-the-scenes disagreements. Instead, it came down to one thing: caution.
“For months Christian Pulisic could have signed the renewal, because everything was ready… they had discussed practically all the details of the contract,” Moretto said. “But the boy took his time and asked for technical guarantees.”
And who could blame him?
Pulisic is 26 now—an age when a footballer’s prime begins to take shape. The next few years will be crucial not only for his club career but also as he prepares to lead the U.S. Men’s National Team into a home-soil World Cup in 2026.
In that context, taking time to consider the direction of AC Milan as a club—especially one facing a season without European football—isn’t just understandable. It’s smart.
A Club in Transition
AC Milan is a club steeped in tradition, but like many giants of the past, they’re also in the midst of a rebuild. The 2024-25 season saw them fall short of expectations domestically and miss out on continental competition. Questions surround the future of several senior players, and the managerial situation remains somewhat fluid.
For Christian Pulisic, who has dealt with the instability of club rotations and short-term planning before, that kind of uncertainty isn’t attractive. It’s not about money. It’s about football. Can the club guarantee him a competitive squad? A clear playing style? Champions League ambitions?
If the answers are yes, the contract will be signed. If not, well… the door remains slightly ajar.
The Gold Cup Absence: A Calculated Call
While all of this is unfolding in Milan, Christian Pulisic has also faced criticism back home. His decision not to take part in this summer’s CONCACAF Gold Cup raised some eyebrows among U.S. fans and pundits.
But again, there’s a rationale behind it. After a grueling season in Italy, the winger has opted for rest. Not laziness, not entitlement—rest. Proper, planned recovery with a view to maintaining peak condition for both club and country as bigger challenges loom on the horizon.
For a player whose career has been haunted by muscular injuries, this summer break might be the smartest move he’s made in years.
What’s Next for Christian Pulisic?
So where does that leave things?
Well, if Milan can provide the “technical guarantees” that Christian Pulisic’s camp has asked for—likely revolving around squad investment, tactical consistency, and perhaps some clarity on the club’s long-term vision—then the American will stay. And not just stay—he’ll thrive.
He enjoys life in Italy. He loves playing at San Siro. He’s become a fan favorite. The climate suits him, the city has embraced him, and the football has brought out the best in his game. By all accounts, he wants to continue wearing the red and black. But only if Milan shows the same level of ambition he brings every time he steps on the pitch.
The Bigger Picture: 2026 on the Horizon
It’s impossible to view Christian Pulisic’s next move without looking ahead to 2026. With the United States set to co-host the next World Cup, Christian Pulisic knows he’ll be under the spotlight like never before.
What he needs between now and then is consistency. Minutes. Matches. Momentum. Milan can offer him all three—provided they stay competitive and focused.
That’s why this contract matters. Not just as a formal agreement, but as a statement. A signal of intent from both sides. Milan wants Christian Pulisic to be the face of their project. Christian Pulisic wants a project worth believing in.
Final Thoughts: No Rush, No Panic
So yes, “the boy took his time.” But maybe, just maybe, that’s the mature thing to do. In a sport that often rushes players into decisions for the sake of headlines and transfer buzz, Christian Pulisic is doing what any thoughtful professional would: taking a step back, asking questions, and making sure the next chapter of his story is written with intention.
Milan fans may have to wait a little longer for that pen-to-paper moment. But if the club gets its house in order and gives him what he’s looking for, there’s a good chance that this partnership—already full of promise—will continue to flourish.
And who knows? Maybe the boy who once ran up the flanks of Dortmund and battled through Stamford Bridge is finally ready to plant his flag and lead a footballing renaissance in Milan.
He just wants to be sure. And you can’t fault him for that.
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