In March 2017, Aston Villa winger Leon Bailey rejected call-ups from Winfried Schafer to play for the Reggae Boyz of Jamaica.
Bailey had been unimpressed by the running of football in the Caribbean country, the Jamaican Football Federation (JFF)—corruption, lack of adequate facilities, incentives, and poor development structures for youth teams.
The former Bayer Leverkusen player agreed to play for Jamaica following the persistence of the Technical Advisor for the Ghana Football Association (GFA)—then head coach for the Reggae Boyz (2009-2013) and Theodore Whitmore (2016-2021).
Raised by his stepfather in Kingston, Jamaica, before moving to Austria in 2011 at the age of 13 to join non-league team Anif Jugend, Bailey opted to play for Jamaica on the condition of his stepbrother being selected too.
He scored his first goal for his country against Antigua and Barbuda in the 2019 CONCACAF Nations League on September 6.
Struggling with the constant “unprofessionalism” with the JFF, the 28-year-old announced in March 2024 that he would be taking a break from the Reggae Boyz.
He cemented his “bad boy” status with the leadership after he was suspended by JFF for turning down a call-up to the 2024 Copa America.
Jamaica are favourites in their matchup against rivals Trinidad and Tobago at the 2025 Unity Cup set to take place in West London on May 27—Ghana takes on Nigeria in a West African derby the day after.