Leon Bailey: 5 Secrets Revealed

leon bailey
Photos courtesy of https://www.instagram.com/kingbailey9

Leon Bailey is one of the most exciting young footballers in the game. The Jamaican is a global superstar whose exhilarating plays on the field and glamorous lifestyle are well documented. But fans cannot know too much about their favourite players: They are curious about the clothing brands they wear, the cars they drive, the homes they own, person(s) they are dating, and even where they get their haircuts. Here are five things you didn’t know about Leon Bailey.

1. Why is Leon Bailey called ‘Chippy’?

Jamaican footballers are well known for having popular nicknames by which fans often refer to them. Many local football fans know Bailey’s nickname is ‘Chippy’ – one he has had since childhood. But how did he come by it? Bailey revealed in a 2017 interview with DW Kick Off that when he was a young boy, his father would say to him, “you know you look like Alvin from Alvin and the Chipmunks?” His friends started calling him ‘Alvin’, then ‘Chipmunk’. They finally settled on ‘Chippy’, which has stuck to him like glue.

2. Which Jamaican community is Leon Bailey from?

Bailey migrated to Europe at the tender age of twelve to pursue his dream of becoming a football star: But where exactly in Jamaica is the Leverkusen winger from? Bailey grew up in Kingston in the well-known community of Cassava Piece, which was also home to Dancehall superstar Mavado, who branded it “Gully Side” during his epic lyrical clash with Vybz Kartel from “Gaza”.

Bailey has spoken fondly about his younger days of playing street football on the Gully Side with the older boys and men. From an early age, he was always a special talent and was able to hold his own against the more mature ballers in the community. The small community of Cassava Piece has produced two superstars in Bailey and Mavado so far. Who will be the next?  

3. When did he first represent Jamaica?

The long rift between Leon Bailey and the Jamaica Football Federation (JFF) is well documented. Bailey was upset with the squad selectors for overlooking his talent for years, only inviting him to the squad after he had exceeded all expectations and became a global star in the game. Consequently, he refused to accept a first call up to the senior team for almost a year before subsequent discussions between his camp and the JFF helped to mend the relationship.

Bailey thus made his long-awaited and much anticipated debut for the Reggae Boyz in 2019, giving local football fans the opportunity and satisfaction of finally seeing the exciting forward run out in the black, green and gold of Jamaica.


However, 2019 was not the first time that Bailey played for Jamaica. He made a maiden appearance for Jamaica’s U23 team back in 2015, scoring a free kick but was not invited back to the national squad in the years that followed despite his impressive performances in Europe.

4. Which high schools did Leon Bailey attend?

There is no fiercer competition in Jamaica than sports rivalries among high schools. The Manning Cup is, without a doubt, the most hotly contested and most watched football competition in the country. There is no better football atmosphere in the land than that created by gifted schoolboy footballers shooting for glory on the field and the raucous fans in the stands and sidelines hyping them on.

While Leon Bailey did not get the opportunity to grace the Manning Cup because of his departure to Europe at an early age, he attended both Kingston College and Jamaica College, two of the most successful schools in Manning Cup history and fierce rivals on the field.

He started high school at Kinston College, spending just one year before moving to Jamaica College: the big stage equivalent of  moving between Liverpool and Manchester United.

5. Who is Bailey’s football idol?

Every young footballer has that special player who they try to emulate; a player who excites an inspires them to reach for the stars. Many young Jamaican footballers have been inspired by the likes of Messi and Ronaldo. For Bailey, Ronaldinho Gaucho, the ever-smiling Brazilian football genius who won the FIFA’s Ballon d’Or award in 2005, was his idol.

In an Interview with ESPN FC in 2019, Leon Bailey revealed that, as a youngster, he was inspired by the legendary Brazilian. “Ronaldinho, the things that he would do with the ball is ridiculous”, he said in awe of the footballing wizard. Bailey went on to reaffirm his admiration for Ronaldinho by saying, “when I was younger, I used to look up to him and I always wanted to be able to dribble pass defenders like that”.