At 6.07 pm on a chilly, stormy Saturday in central Ohio, Giorgio Chiellini reached a crossroads that no professional athlete can avoid. The 39-year-old center-back, who has played for Major League Soccer’s Los Angeles FC since July 2022, must now decide whether to continue a career that featured numerous team and personal honors for Juventus and Italy. (Chiellini later announced his retirement) Chiellini’s contract expired when the host Columbus Crew defeated LAFC, 2-1, to win the 2023 MLS Cup. A victory would have given the veteran his second consecutive MLS Cup win to go with nine Serie A titles for Juventus and Italy’s 2020 European championship. “The club is open with me and gave me the total freedom to decide but I still have doubts. I have to understand what I have to follow, if it’s my head, if it’s my heart, if it’s my leg,” says Chiellini, referring to a torn anterior cruciate ligament in his right knee, which he injured in 2018. “I need to take a break for a little bit and enjoy the family for two or three days. I’ll go back to Italy and then I’ll have a final decision.” But if Chiellini decides not to return for a 25th professional season, he can build on a foundation he started constructing when he arrived in California. Chiellini wants to take his passion for soccer from the pitch to the executive suites. That goal provided a major motivation for the defender to come to MLS and join LAFC. “For sure, soccer is my world and my future,” he says. “I never think about a life without something related to soccer, to be honest. I was also interested in sports business and the point of view on the American side.” Chiellini has the credibility to pursue a business career. He earned his bachelor’s in economics and commerce at the University of Turin in 2010, then received his master’s in business administration there in 2017, graduating with honors. “I grew up thinking about going to university,” says Chiellini, who wanted to pursue medicine like his father before soccer became a full-time job. “I was alone. I was reading a lot of books. I was spending a lot of time playing PlayStation or sleeping in the afternoon or something. Why cannot I use this time to continue to study? “It was also a challenge and I love a challenge. I want to challenge myself every day in order to improve myself.” But Chiellini needed to arrange his academic program, including his exams, around training and playing. When he had to miss classes, the university provided Chiellini with private tutors. The defender even studied during team flights, arousing his teammates’ curiosity. “At the beginning, people around me said, ‘What are you doing?’’ Chiellini says. “But after a couple of times, it became normal.” In the same year Chiellini completed his master’s, his brother Claudio made it known that the defender wanted to play in the United States. Claudio, working as Juventus’ loan coordinator, met Will Kuntz, LAFC’s assistant general manager, at a networking function. Kuntz was preparing LAFC to take the field for its first season in 2018. “I thought this was a really exciting way to potentially bring in some Italian prospects looking to develop with us and create a pathway,” says Kuntz, now the Los Angeles Galaxy’s general manager. “Claudio said, ‘I think my brother might like to come play with your club when he is done playing in Europe.’ I thought, ‘Well, that’s probably a long time from now.’ “ When North Macedonia eliminated Italy from World Cup qualifying in March 2022, that time arrived. Kuntz held a Zoom meeting with John Thorrington, LAFC’s vice-president of soccer operations, and Steve Cherundolo, the manager. “I went to Steve and John and said, ‘Listen, guys, I don’t know if this is real but, not for nothing, this is the latest,’” Kuntz says. “Steve said, ‘OK, we have to run this one down.’” Claudio Chiellini put Cherundolo in contact with his brother, who watched LAFC’s matches and texted Cherundolo about them. Team officials responded by watching Chiellini’s final games with Juventus and Italy. “Giorgio was so clear on what he was looking for,” Kuntz says. “Based on his stature with the club and his standing with the Italian national team, it was a relatively easy conversation to get him released from his contract.” Not even MLS’s salary cap dissuaded the veteran defender. “We said, ‘We only have this much and it’s a fraction of what you have been earning for your entire career,’” Kuntz says. “He said, ‘No, this is great.’ It was really a special instance of all the stars aligning.” LAFC not only got a world-class defender but an avid student whose aptitude for sports business was “off the charts,” Kuntz says. “He was very intentional not only in everything he did but in the way he spoke about the game and the business of the game, his understanding of how contracts work, how the league was structured. He made it known he wanted to continue working on the club side of things when he was done.” That meant discussions with club officials and members of LAFC’s large ownership group, which includes Alibaba founder Joseph Tsai, Mandalay Entertainment CEO Peter Guber and NBA Hall of Famer Magic Johnson. Chiellini wants to know “why people invested in soccer 10 years ago, how to decide to build a stadium or to build facilities, how to invest $15m, how to make these main decisions.” He also wants “to know what a lot of owners did in their past lives … Just knowing the story of these people could help you open your mind to some ideas in the future. In the end, a lot of information helps you to have new ideas, not just to copy somebody else.” Chiellini quickly learned the difference between the American and European approaches to sports business. “First of all, it’s much more entertainment than life or death [in America],” he says. “There are a lot of things to do for the family. You are not just there for 90 minutes. You could be there for three hours, six hours. You could spend all day close to the stadium or arena to live a different experience. That’s the biggest difference that I found from Italy, for sure.” Chiellini’s potential excites Thorrington. “Whenever he engages with myself and ownership,” he said, “it is clear he has the intellectual horsepower and capacity to be of great value to any club once he is finished playing.” That intellectual horsepower also made a major impact on the pitch. “He’s analyzing everything at all times,” LAFC right-back Ryan Hollingshead says. “He sees the game in such a unique way that he always has a thought. You just pick up so many of these little nuances. Those little details just add up so much throughout each game throughout the season.” Chiellini even fundamentally changed Hollingshead’s approach. “In the past, not every play was do or die,” he says. “If I position my foot one yard to the right or to the left, who cares? But when you start dissecting the game, it causes you to be in the right spot in the right moments. The whole game changes because of one little play, one little yard. “In my 10 years of playing professionally, he has been the most actively vocal player I’ve ever played with in trying to dissect the game in those ways. It’s just been so sweet to watch.” Cherundolo, who played 15 seasons for Hannover 96 and represented the United States in two World Cups, noticed Chiellini’s influence beyond technical analysis. “He finds a very good balance of, at the right times, finding the right words and communicating with the group, whether it’s non-verbally or verbally,” Cherundolo says. “He’s just a natural-born leader and a presence in the locker room that every team needs but not every team has.” For his part, Chiellini believes MLS has a promising future, especially after Lionel Messi joined Inter Miami. “The Messi deal was, I think, a huge change and a huge boost for soccer in the US,” he says. “It’s something that you could compare to the [David] Beckham arrival. All of the stadiums are crowded, almost 20,000, 25,000 a game. It’s not reached a level of [NFL] or other sports or sports in Europe where you’re getting 40,000, 50,000, 70,000. But it’s growing up very, very fast and in a sustainable and solid way. That’s important. “I think now, with the Copa América, the Club World Cup and the World Cup coming soon, it’s a good cycle that we have to use in order to improve soccer in the US. But the good thing about the league is that it’s very elastic about rules. It’s one of the few leagues all over the world that could really change many things from one season to another. That’s a good thing because it’s a league that now has to take advantage and change in order to grow.” With Chiellini stepping away, a position on the touchline or in the boardroom appears inevitable. “I know Juventus wants him,” Hollingshead says. “I know that they’re going to try to get him an offer to come back to Italy. I don’t know in what role. But for him not to be in some sort of coaching, GM, recruiting role, something would just be a disservice. I know that’s his desire. I know that’s what he’s looking forward to and it will be really fun to follow along. “But for now, he’s still playing at a really high level and, man, he’s so crucial for our team that we can’t let him go yet.”