After a promising start to 2025, AC Milan’s struggles have resurfaced, falling short of the expectations set at the beginning of the 2024–25 season. Their ongoing woes were on full display in a 2–1 defeat to Napoli, where a missed penalty by Santiago Gimenez — handed to him by Christian Pulisic — became one of the game’s turning points.
Milan traveled to the Diego Armando Maradona Stadium for Matchday 30 in Serie A, hoping to boost their European qualification hopes. However, they quickly fell behind, with Napoli jumping to a 2–0 lead by the 19th minute.
In the second half, a moment of controversy emerged when referee Simone Sozza awarded Milan a penalty following a foul by Philip Billing on Theo Hernandez in the box. Although USMNT star Christian Pulisic is Milan’s designated penalty taker, he chose to hand the opportunity to Gimenez instead.
The Mexican striker stepped up in the 69th minute looking to cut the deficit in half, but Napoli goalkeeper Alex Meret guessed correctly and saved the low, driven shot. Minutes later, manager Sergio Conceicao replaced Pulisic with Luka Jovic, who managed to pull one back — though it wasn’t enough to salvage a result.
The decision to let Gimenez take the spot kick raised eyebrows, especially considering a previous incident. In Milan’s 2–1 loss to Torino last month, Pulisic missed a penalty, and reports suggested tension between him and Gimenez over who should take it. This latest moment reignited concerns over Milan’s penalty strategy.
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Milan’s penalty struggles in Serie A
Penalty kicks are often seen as golden opportunities — statistically, around 75% are converted, while 17% are saved, 4% go wide or over the bar, and 2% hit the woodwork. Yet, for AC Milan, penalties have become a recurring problem this Serie A season.
Of the eight penalties awarded to Milan so far, only half have been converted — a concerning rate for a club aiming to compete at the top. Christian Pulisic has scored three, and Tammy Abraham has added one. However, costly misses from Pulisic, Abraham, Theo Hernandez, and now Santiago Gimenez have exposed a deeper issue.
The lack of a consistent and confident penalty taker has become symbolic of Milan’s broader struggles. For a squad filled with attacking talent, such inefficiency from the spot has directly impacted results and raised questions about leadership and decision-making in crucial moments.
