USMNT star Christian Pulisic’s career-defining summer starts now as AC Milan’s season goes down to the wire

For a while there, Milan were feeling pretty good. They were chasing down Inter at the top of the Serie A table, even if that chase always looked unlikely given how good their crosstown rivals were. At the very least, Milan looked set for a return to the Champions League, which would be much appreciated after missing out on European competitions altogether this season.

Suddenly, though, that Champions League spot is far from guaranteed. Dating back to March 15, Milan have won just two of their last eight games while also drawing one in that span. That means the club has collected just seven points from eight games down the home stretch after previously going unbeaten from Aug. 29 until Feb. 22. For most of the season, Milan couldn't lose. Suddenly, they can't win.

As a result, Milan have slumped right on down to fourth with two games remaining. They're three points behind second-place Napoli and one point behind third-place Juventus, yes, but the more concerning part is where they lie compared to those behind them. Just three games ago, Milan had an eight-point gap between themselves and fifth place. Now, that gap is zero.

Roma are level on points for fifth, while Como are two points back for sixth. Fourth place is Champions League, fifth place is Europa League, and sixth is Conference League - there's no overstating the difference in money and prestige that comes with those particular competitions.

For Milan, it's imperative to finish in a Champions League place. To get there, they'll likely need something close to the best version of Pulisic.

Ahead of Milan's 3-2 defeat against Atalanta this past Sunday, a match that included walkouts from sections of the club's fans, Pulisic was ruled out due to injury. He was dealing with a glute issue, reports said, and, at this point in the World Cup cycle, that revelation sent shockwaves through American soccer.

The good news, according to reports since, is that the issue is not considered serious, and Pulisic could be back in the XI this weekend. There is no guarantee, though, and rushing back before a home World Cup would carry obvious risk, even with Milan in a difficult spot. That is what makes this such a tricky moment: Milan could use him, but Pulisic has not quite looked like himself.

That has been the story for much of 2026. Pulisic still has not scored this year, and while Milan’s slide goes well beyond one player, his drought has not helped. It is why, according to reports out of Italy, Allegri could turn to Christopher Nkunku and Niclas Fullkrug in attack for the next match, particularly if Pulisic is not fully fit.

Whether he plays or not, though, Pulisic's future may be on the line, much like all of Milan's stars.

Milan’s failure to qualify for the Champions League shaped their entire summer. The club had to balance the books, leading to the departures of Tijani Reijnders, Malick Thiaw and Theo Hernandez. Some of those exits may have happened regardless, but Milan were never really in position to properly reload with the money they brought in.

Pulisic has been linked with a potential departure for some time now. When he was in strong form, reports from all over Europe said big clubs were after him and, even amid this cold streak, those reports haven't fully dried up. In recent months, Manchester United, Liverpool, and Tottenham have all been linked with the American star. He has also not yet signed a new deal, which would theoretically open the door for a potential transfer with just 12 months left on his current contract.

According to former Milan star Massimo Ambrosini, selling Pulisic would be a massive mistake, even if Milan do need to earn some money this summer.

“I think Milan need him," Ambrosini told GOAL in March. "I'm surely convinced of that. I don't know what his relationship with Allegri is, I don't know exactly. I don't know what's the plan of Allegri for the next year. Of course, AC Milan with Champions League, they will need five or six players more. And I don't know if they have the money to buy four or five new players. So I don't know if they are obliged to sell somebody. This is the question. This is the problem.

“It may be if Allegri wants five or four players and the club says, ‘OK, we don't have enough money, we have to sell somebody’. I don't know if Christian would be in this situation. But for me, if I were the coach of AC Milan, he would stay in Milan, of course.”

As Ambrosini says, the hope is that it doesn't come down to that. To ensure that, Milan need to win.

There is good news: the schedule makers have been kind to Milan.

First up is Genoa on Saturday, a match against a team sitting 14th with little left to play for. After that comes Cagliari, currently 16th and potentially safe by the time they visit Milan. Both games are winnable. Milan may need to win both to reach the Champions League.

They are, to borrow the old cliche, two cup finals. The difference, in Milan’s case, is that they may only feel that way for one side.

That home stretch will be over soon, and almost immediately, the focus will turn towards the World Cup. Just two days after Milan's May 24 season-ender against Cagliari, the USMNT's World Cup roster will be announced in New York City. Pulisic is certainly expected to be on it. What version of him will arrive stateside, though? Will it be one full of confidence after helping his club back to where it belongs, or will it be one that still has questions to answer in both the short and long term?

Again, back to Pochettino's big point, everything matters now, particularly for Pulisic. This summer was always going to be career-defining, but that idea may take on additional meaning depending on how these next few weeks shake out.