Milan’s season has already been marked by several dramatic moments, but few have been as chaotic and embarrassing as the penalty debacle against Fiorentina last October. In that infamous match, the club’s designated penalty taker, Christian Pulisic, was twice denied the chance to take a spot-kick by his own teammates. First, Theo Hernandez took control of the ball, and then, with the complicity of Fikayo Tomori, it was Tammy Abraham who stepped up.  In that match, Milan players argued over who would take a penalty—twice.

The result? Both spot kicks were missed, leaving fans and the coaching staff in shock. “Our designated penalty taker is Pulisic,” the then-coach Paulo Fonseca said after the match. “I don’t know why the players changed their minds. I have spoken to them and told them that this can’t happen again.”

Now, with the arrival of Santiago Gimenez, the question arises once again: Who should be the Rossoneri’s main penalty taker? Should they stick with Christian Pulisic, who has a perfect penalty record? Or should they turn to Gimenez, a proven goalscorer who has also been reliable from the spot?

Pulisic still first choice?

Luckily, there have been no further tumultuous incidents since the introduction of coach Sergio Conceicao. Pulisic has been perfect from the spot throughout his professional career, scoring all 12 penalties he has taken for club and country. For Milan, he has already converted three out of three, two in Serie A and one in the Italian Super Cup.

Given this flawless record, there seems little reason to change a system that works. Even Milan fans have voiced their support on social media, with one commenting on X (formerly Twitter), “It should be Pulisic. If it isn’t broken, don’t fix it.” Another added, “Pulisic hasn’t missed a single pen so far, so he should be the first taker. Don’t change something that works well.”

Could Gimenez take over?

The situation becomes more intriguing with the arrival of Santiago Gimenez, Milan’s newest attacking signing. The Mexican striker is also an accomplished penalty taker, having scored 15 penalties in his career, including a recent one against Bayern Munich in the Champions League. However, unlike Pulisic, he has missed four penalties, two while playing for Feyenoord and two for Mexico.

This has led to mixed opinions among fans. Some believe that as the main striker, Gimenez should be taking penalties by default. “Old school on that one, the striker should take penalties,” one fan argued. Another supporter pointed out, “I saw Pulisic shooting penalties, and I guess they were a bit predictable for the keeper. If Gimenez shows his skill in training, I wouldn’t mind him trying out.”

At the same time, others suggest a pragmatic approach, allowing both players to share the responsibility depending on the match situation. “Pulisic for now. I’m assuming we’ll rest him for some games now that we brought in Joao Felix. When Pulisic is out, Gimenez, as the starting striker, should take them.”

Who will Conceicao choose?

Ultimately, the decision will rest with Sergio Conceicao, who may implement a flexible penalty-taking strategy. The most logical approach would be for Pulisic to remain the first choice, given his flawless record, with Gimenez stepping up when Pulisic is unavailable or rested.

There is also a chance that the Portuguese boss could consider other options. Tijjani Reijnders and Theo Hernandez are both capable penalty-takers. But one thing is certain—under Conceicao’s leadership, the Rossoneri won’t repeat the chaos of the Fiorentina match.