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The semiannual matchup between AC Milan and Juventus is one of those fixtures that fans make note of at the start of the season. After all, these are two of the most decorated teams in Serie A history, with Juventus winning 36 league titles and Milan having claimed 19.

In this instance, Juventus is trying to chase down the Rossoneri for second place in the league standings. AC Milan is trying to shake off the bitterness of seeing Inter Milan clinch its 20th league title in the Milan Derby — also known as the Derby della Madonnina — last weekend. But the current campaign has seen a different flavor added to this Sunday’s matchup, that being the presence of American players. Christian Pulisic and Yunus Musah will be available for Milan, while Weston McKennie and Tim Weah will be in the mix for the Bianconeri.

While the Serie A campaign is littered with derbies, this match always catches the eye. “It’s a game that gives you goose bumps,” said McKennie about the matchup during a Zoom call with reporters last week. “And it’s a game that … just looking at the atmosphere can make someone that doesn’t know anything about soccer want to follow it.”

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Pulisic and McKennie in particular have enjoyed outstanding seasons, and the pair figure to play prominent roles this weekend. Pulisic has scored 13 goals in 44 league and cup matches, putting behind him a four-season spell with Chelsea when, although he was part of a UEFA Champions League-winning side, he never quite became the mainstay he hoped to be. In Milan, Pulisic has benefited from the kind of trust from manager Stefano Pioli that came only in flashes while in London. (Unfortunately for Pulisic, some reports suggest Pioli will be fired at the end of the season.)

McKennie had some more painful Premier League memories to banish, having endured a loan spell with Leeds United last season that ultimately ended in relegation. Even his previous seasons with Juve saw him endure some ups and downs under manager Massimiliano Allegri. But this season, he has returned to Juve to lead the team with nine assists while putting in his usual hardworking shifts in the Bianconeri’s midfield.

So on Sunday, the two U.S. internationals will infuse some red, white and blue into one of Italy’s most anticipated matches. And that will add another chapter to a friendship that is entering its second decade — one that started at a youth camp in Carson, California with, as Pulisic joked, “[McKennie] being annoying as he is and, yeah, me just putting up with it.”

But even beyond the friendly banter, the sight of two Americans playing significant roles for two of Serie A’s heavyweights is striking. While U.S. players have long found homes in places such as Germany, England and even France to a degree, American success in Italy has been sporadic at best. Alexi Lalas paved the way in the modern era with a two-season spell in Serie A with Padova in the mid-1990s. Fifteen years later, Michael Bradley enjoyed some productive seasons in Italy, first with Chievo Verona and later AS Roma. Venezia’s Tanner Tessmann and Gianluca Busio are both aiding their club’s promotion push from Serie B. That’s been about the extent of the U.S. highlights.

The reason for Americans making such limited inroads is multifaceted. Italy has long had tight restrictions on foreign players. At present, Serie A limits teams to two non-EU players each; the fact that Pulisic, Weah and Musah all possess EU passports has helped them get around that restriction. Serie B and Serie C don’t allow any at all. (Tessmann’s arrival took place in 2021, during Venezia’s most recent season in Serie A.)

Historically, Serie A’s standing in the sport’s global pecking order also played a part, in that it was once the top destination for emerging players. This was especially true during the 1980s and 1990s, when the likes of Diego Maradona, Ruud Gullit and Ronaldo Nazario graced its fields. That meant only the best of the best were coming to Italy to play, which often meant American players wouldn’t even be considered.

There’s also the language barrier, which can make it tougher for players to adapt. Even in Germany, as well as places such as Belgium and the Netherlands, English is spoken with enough frequency to ease the assimilation process. Both Pulisic and McKennie noted that the language has been the toughest hurdle to overcome in terms of adapting to Serie A. “I didn’t really have a translator,” said McKennie about his arrival in 2020. “I’m just sitting in meetings like, ‘Uh, what’s going on?’ And then I’m expected to do it on the field straight away.”

So what has changed?

First, the influx of American owners into Italian soccer has been significant. There are five teams in Serie A — Atalanta, Fiorentina, Genoa, AC Milan and Roma — owned by Americans. That number swells into double digits when you go down into Serie B and Serie C.

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Weston McKennie reflects on his development in Serie A

Weston McKennie explains how he has developed in Italy and speaks about the importance of playing in Europe.

Italy has long been viewed as an undervalued asset, even going back to the time when Joe Tacopina first set up shop in Venice. (Venezia is now run by another American, Duncan Niederauer.) That investment has been combined with more institutional knowledge of the American market within Italian clubs, and the presence of an American player can serve to increase a club’s marketability. That push is continuing ahead of the 2026 World Cup, as Italian teams are eager to make their mark in the U.S. with Serie A opening an office in New York.

“I deal with a lot of the owners, and they are definitely looking to the U.S.,” said Charlie Stillitano, who, when he isn’t co-hosting a soccer show on Sirius XM, works as the president of Serie A USA, an entity overseeing the league’s interests stateside. “They understand the U.S. market, and they want to build their brand here.”

Serie A’s cachet isn’t what it once was either, as the huge influx of money from broadcast rights into the English Premier League has meant the English league is now well on top. One need only look at the arc of Pulisic’s career to realize that Serie A doesn’t carry the clout it once had. Chelsea paid $73 million to Borussia Dortmund when it signed Pulisic in 2019. Milan paid less than a third of that amount — $22m — when it brought the U.S. international on board before this season.

There’s also the considerable increase in the ability of American players. Alex Menta, previously the sporting director at Venezia and now holding the same role with Serie C side Triestina, told ESPN that decision-makers in Italian soccer have long admired the mentality of U.S. players. But now U.S. players are bringing more to the table. Menta feels American players are “super professional” and bring a PR savviness with them that can help raise a club’s profile in the U.S. market. Underpinning all of that is an increase in skill level.

“Between the influx of American owners, and American talent growing, that’s been kind of the perfect equation for more of them ending up here,” Menta said. “But the thing is, ending up somewhere is great. Working out well is a whole different story. And so the mixture of mentality and skill is why they can stick. American ownership is probably why they’re getting that chance. The bridge from Italy to America is shortening every day in the football landscape.”

When it comes to foreign players setting up shop in a particular country, there is such a thing as proof of concept. That beachhead has now firmly been established. “American players now in Italy are not seen as American players,” said Stillitano. “They’re seen as professional soccer players. I think they’re seen in the same vein as any other guy that gets [to Italy] from Belgium or from Holland.”

Marco Tieghi is an Italian and American sports lawyer with his own Milan-based sports consultancy. He worked with MLS to help arrange the deal that brought Andrea Pirlo to New York City FC back in 2015 and has also provided advice to Italian clubs. He has noticed increasing interest from Italian clubs as it relates to bringing in American players.

“Clubs here in Italy are starting to ask me, ‘Hey, we want a McKennie too,’ or, ‘We want those kinds of players that are very physical and athletic’, because then they see that they’re also technical now, you know? It’s not only athletic [ability]. I mean McKennie, Pulisic, Musah, Weah, they’re very technical players. At the same time, there’s a sort of a ‘Wow, there are players there.’ So they’re starting to do scouting. They’re sending people to the U.S to watch youth tournaments.”

Players have to be convinced of Italy as a destination, too. Experiences, good and bad, are shared among players, especially when they meet up for international duty. And clearly, the bright lights — and bigger paychecks — of the Premier League will often still carry the day. But there are alternatives, and to hear Pulisic and McKennie discuss their time in Italy, they’ve experienced plenty of growth in terms of their respective games. It needn’t be a situation where it’s “Premier League or bust.”

“I think the league helped me grow, and [from] more of a tactical standpoint and positional standpoint as well,” McKennie said. “I was in Germany before, and I was the workhorse still and I was running everywhere and trying to get into everything and maybe running 60 yards when I only need to run 20 and get the same job done.”

Pulisic noted that he’s been surprised at how difficult some of the games have been and that he has been tested. The consistent playing time and trust from his manager have meant the world to him as well, with him adding “I’m loving every second of it.”

Perhaps in time, more American players will enjoy a similar experience.





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