'Only two reasons' - Brad Friedel thinks he knows why USMNT star Christian Pulisic hasn't signed new AC Milan contract

Pulisic is tied to terms at San Siro through to 2027, with the option for a further 12 months to be triggered beyond that point. Milan have, however, been looking to add at least another year to that agreement, while delivering a pay rise that recognises the 27-year-old’s value to their collective cause.

Despite several rounds of discussions, talks have now been put on hold with no paperwork completed. It was suggested over the summer that Pulisic wanted to wait and see how the Rossoneri rebuilt - after missing out on European qualification last season - before committing to anything.

Massimiliano Allegri has led Milan to the top of the Serie A table, but their talismanic American forward continues to delay any progress on the contract front. Could that be because he is not entirely convinced that his peak years should be spent in Italy?

Quizzed on whether Pulisic is leaving the door open to potential suitors, ex-USMNT goalkeeper Friedel - speaking in association with ToonieBet - told GOAL: “I think it suggests that he is leaving his options open. When I was at clubs, I always wanted to sign my contracts when I was happy at places. I can only go on personal experience, I liked having multiple years on the contract - you never know with injuries around the corner. If I was truly happy at a place, I really enjoyed having two or three years on a contract.

“There are only two reasons for not signing. One, you are not happy with the contract. Two, you are keeping your options open. Maybe he has given a verbal commitment. I would assume that he is keeping his options open. If you are happy somewhere and you are happy with the numbers, you sign the contract.”

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Pulisic has already represented Borussia Dortmund and Chelsea, becoming a Champions League winner during his time at Stamford Bridge. Asked if the talented forward is considering something different, rather than bigger and better, Friedel added: “The only other thing that can come into play is if you aren’t convinced about the club itself. The way he is playing, it doesn’t seem like that’s the reason - he plays really well every week for them.”

Pulisic has posted career-best numbers with Milan, scoring 17 goals last season, but has seen a return to England speculated on - with Manchester United reported to have him on their recruitment radar.

Friedel has previously told GOAL of the advice that he would offer Pulisic: “It’s a huge club that is underperforming. I know he did well last season, but they finished eighth. If AC Milan are finishing in eighth, that means people are losing their jobs - which did happen last year. “If I was advising him, I would be looking at teams in Europe and seeing what’s happening at AC Milan, for sure. I would make sure, especially in World Cup year, that my client is playing. He is playing, so that’s the best thing. But I think I would have an eye open somewhere else.”

Pulisic does have a home World Cup to think about at the end of the 2025-26 campaign, with FIFA’s flagship event heading to the United States, Canada and Mexico. The group stage draw for that tournament will take place on Friday.

As a contender to captain his country next summer, Pulisic will want to be in the best possible form when a shot at global glory rolls around. It could be that he uses the World Cup as a shop window, with Milan aware that they will need to cash in at some stage if a lucrative contract proposal remains unsigned.