Raiola was born in 1967 in Nocera Inferiore, Salerno, in southern Italy. He moved to the Dutch city ofHaarlem a year later with his parents. Growing up in the Netherlands, his father opened a successful restaurant business where Raiola spent his younger years working as a waiter. At the same time, he obtained his high school diploma and attended university for two years, enrolling in the Faculty of Law. He speaks seven languages: Italian, English, German, Spanish, French, Portuguese and Dutch. He started playing football for the youth team of HFC Haarlem, but stopped at age 18 in 1987 to become head of the youth team. After a brief venture as a player and administrator, Raiola remained involved in the football world, this time as a football agent. He began working at Sports Promotions, a sports agent company, and assisted in the transfers of several high-profile Dutch players to Italian clubs, including Ajax player Bryan Roy, Marciano Vink, Wim Jonk and Dennis Bergkamp and Michel Kreek. After a while, however, he decided to leave the company and start his own business. His first independent big transfer was Pavel Nedvěd's signing from Sparta Prague for Lazio following his impressive performance at UEFA Euro 1996, where Nedvěd's Czech Republic reached the final. More than 20 players playing in European leagues are represented by Raiola. He currently resides in Monaco. In 2008, he was involved in two disciplinary hearings instigated by the Federazione Italiana Giuoco Calcio for transfer irregularities. In August 2016, after closing the world record transfer of Paul Pogba to Manchester United, Raiola made a reported €25 million from Pogba's €105 million transfer; he bought the former Miami home of one of America's most famous mob bosses, Al Capone, for €9 million. On 8 May 2019, Raiola was banned by the Italian Football Federation from acting as an agent representative for three months for undisclosed reasons, while his cousin Vincenzo Raiola was banned for two months. On 10 May, the bans were extended worldwide with the decision from the FIFA Disciplinary Committee. On 13 June 2019, Raiola and his cousin won their appeals against the three-month ban, revoking the ban. On 22 January 2020, Raiola was among a number of high profile football agents including Jorge Mendes and Jonathan Barnett who threatened FIFA with legal sanctions following the planned cap on transfer payments.