Why Santiago Gimenez and not Christian Pulisic? Milan boss Sergio Conceicao offers peculiar rationale for Napoli penalty confusion in Serie A

Milan’s trip to Naples ended in yet another disappointment. A 2-1 defeat to Napoli pushed the Rossoneri further down the Serie A table, leaving their hopes of qualifying for the UEFA Champions League hanging by a thread. However, one moment in the match stood out beyond the result—when Santiago Gimenez stepped up to take a crucial penalty instead of Christian Pulisic.

With Milan trailing 2-0 in the 67th minute, a golden chance arrived when Theo Hernandez was fouled in the box. Given Pulisic’s excellent record from the spot—having missed just one penalty in his career—most expected him to take responsibility. Instead, the ball was handed to Gimenez, a player who had not scored in over a month.

The result was disastrous. The Mexican’s weak effort was comfortably saved by Alex Meret, denying the Rossoneri a lifeline. Just minutes later, Luka Jovic did manage to pull one back, but it was too little, too late. The penalty miss proved decisive, leaving fans and pundits alike questioning: Why did Milan allow a struggling striker to take such an important kick when Pulisic was on the pitch?

What did Sergio Conceicao say?

After the match, Milan manager Sergio Conceicao was asked about the decision, and his response left many scratching their heads. “We have three main takers. Pulisic wanted to give confidence to his teammate who hasn’t scored for a few weeks,” Conceicao told DAZN. “We know how things are. It’s not up to me to say something to the players, it’s the three of them who decide based on how they feel.”

In other words, this was not a managerial decision. Instead, it was the American himself who chose to let Gimenez take the penalty—a gesture aimed at boosting the Mexican striker’s confidence.

The Portuguese boss framed this as a sign of unity within the team’s dressing room, but the decision ultimately backfired. Gimenez’s confidence was clearly low, and the missed penalty only added to his struggles. Meanwhile, Milan’s slim chances of salvaging a result evaporated.

Costly decision for Milan

Milan’s fourth defeat in six league games leaves them ninth in Serie A, four points behind Fiorentina and nine points off fourth-placed Bologna. With Champions League qualification slipping away, every point matters. The decision to allow an out-of-form striker to take a must-score penalty could prove costly when the season ends.

Pulisic remains one of Milan’s most reliable performers, having already scored 15 goals this season—including four penalties. But in this moment, his generosity, unfortunately, cost Milan dearly. As Conceicao put it: “There’s great frustration because we didn’t deserve this defeat.”