Leon Bailey’s fight with Jamaica’s football federation is a long-running family affair

There was one significant absentee as the USMNT beat Jamaica 3-1 after extra time on Thursday evening.

Leon Bailey, the Jamaican team’s born-and-bred star, had been left out of the squad by head coach Heimir Hallgrimsson for this month’s CONCACAF Nations League internationals.

Bailey is in the form of his life, having registered eight goals and eight assists for Aston Villa in 27 Premier League appearances this season. When news broke that he was not in the squad, fans roared in protest. Why would you leave out the nation’s best player?

The answer lies in the aftermath of Jamaica’s 3-2 win against Canada in November’s Nations League quarter-final second leg in Toronto, when Bailey and forward Trivante Stewart were found to have broken team rules by leaving the hotel after curfew. “We have many agreements between the staff, the coaches, and the players, but we have only one rule: Don’t leave the hotel after 10pm,” Hallgrimsson said. “These players didn’t even sleep at the hotel.”

As a result, they were handed an internal suspension for the next international window, which we are now in the middle of. Once they have served these suspensions, Hallgrimsson added the players would be considered for selection as normal moving forward.

“We are finished with this,” Hallgrimsson said. “Both players took responsibility for their actions, apologised to us and the squad, and accepted the apology. We all make mistakes in our lives, even the best. For all of us, it’s a case closed, and we move on.”

After Hallgrimsson confirmed his omission by phone a few days before the squad announcement, Bailey travelled to Jamaica during the international break to spend time with friends and family.

While there, the night before Jamaica’s Nations League semi-final against the USMNT in the Dallas Cowboys’ AT&T Stadium, he sat down for 47 minutes with the “Let’s Be Honest” podcast, during which he called out the Jamaica Football Federation (JFF) over what he says is a lack of professionalism and poor facilities.

So much for “case closed”.

Bailey has been a key part of Villa’s 2023-24 season (Marc Atkins/Getty Images)

“People don’t know, most of the time, I book my own flight to make sure I reach the national team,” Bailey said. “(The JFF) are very unprofessional. They send my flight details to me at 11pm to travel the next day. A lot of the time, I book my flight, but the national team does not pay me. I don’t remember the last time I received one dollar from the national team. All of my time with the national team is very unprofessional. In ways that you can’t even imagine.

“You turn up, and there is not even equipment for you. There is no shirt. They tell us to find our own shorts. Sometimes, they provide us with women’s shirts. In terms of travel, it is ridiculous. It is a lot. Whenever I’m there, they don’t know how to operate. I’m not expecting them to know all these things, but it is not like I am a normal player.”

The JFF disputes these claims, describing them as “inaccurate and contradictory”. According to the federation, Bailey travelled on flights booked by the JFF in each of the three most recent international windows, and on five of the six flights he caught during this period his seat was in business class.

Still, his assertion that he is not a “normal player” holds up to some scrutiny.

Bailey is easily one of the most famous Jamaican-born footballers ever, and likely the most well-known Jamaican male international sportsperson of any type since sprinter Usain Bolt.

“When we go to places, I feel exposed,” Bailey said of his time with the national team. “Anybody can just run up to me and put a camera in my face or do whatever they like. All the time, when we play a game anywhere, it is Leon Bailey that they are coming to see. Who do you think they want to see most of the time?

“ I’ve never voiced these concerns, because I try to mesh with everyone. I am not that person. I want the team to do well, so I can’t make it feel like I am better than anyone else.

“The Jamaica national team is not doing anything for me. They can’t give me exposure. Playing for them won’t make Real Madrid call me. I’m playing overseas and repping my country. Everywhere across the world, people know Leon Bailey. I can’t remember the last time I went somewhere and someone didn’t know me.

“I don’t ask for money. I only ask for a proper flight and a room by myself, and I can’t get that. What am I here for? I’m exposed to injury.”

Not for the first time, Bailey now says he is taking an indefinite break from international football.

“They always want me to play for Jamaica, but I’ve had personal problems with the association since I was 11 or 12,” Bailey said in 2017, while playing for Bayer Leverkusen in the German Bundesliga. “Jamaica could have had me a long time ago, but there are reasons why I’m not playing for Jamaica. I’m focusing on the club now.”

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Bailey has said he would not play international football before, but later returned (Omar Vega/Getty Images)

His complicated relationship with the JFF stems from his father and agent, Craig Butler, another of Jamaican football’s most influential and famous people. Butler adopted Bailey and 22 other children, with Bailey living with him from the age of eight. Bailey was born in Cassava Piece, north of Jamaica’s capital city of Kingston, an underprivileged area known for gang violence.

“My first wife had kidnapped my three-year-old son, CJ, and took him away after a bitter divorce,” Butler told The Athletic in 2023. “I didn’t know what to do, but one of my aunts told me to put it in ‘God’s bank’. I asked her what she meant. She said, ‘Every time you see a little boy that needs help, help him, and wherever CJ is in the world, you will be able to withdraw the kindness from God’s bank, and you will be protected’. So it started with Leon coming.”

Before setting up his own academy, Butler worked as a manager for electronics company Toshiba. On the side, he engaged in passion projects relating to football. He ran a campaign to ensure Jamaica had the facilities to travel to the men’s World Cup in France in 1998 and worked in academy football, coaching players including future Villa and Brazil striker Wesley and Leicester City and Nigeria midfielder Wilfred Ndidi.

Bailey was given the nickname ‘Chippy’ after moving in with the other children Butler fostered. It was meant affectionately due to Bailey’s apparent resemblance to Alvin from the Alvin And The Chipmunks film. Along with Kyle Butler, Craig Butler’s biological son, he began playing for the academy’s team, Phoenix All Stars, formed in 2011.

Butler, now CEO and president of the Phoenix academy, set up the initiative to develop Jamaican talent, using football to offer direction to young adults and teach the importance of “brotherhood, loyalty and moral and social responsibility”.

At the same time, Butler was battling with the local and national federations. Before Phoenix, he was in charge of the Stony Hill football academy, around 5km from Cassava Piece.

From 2007, he was engaged in discussions with the Kingston and St Andrew Football Association (KSAFA) to allow Stony Hill to compete in its leagues and tournaments for the first time in over a decade. When he succeeded, local businessman Livingston Payne emerged and claimed he was the club’s owner, not Butler. KSAFA advised both men to lead the club together, and Butler took the association to court.

While Butler’s case was in motion, Rudolph Speid took over from Stewart Stephenson as KSAFA president. In some ways, Speid’s involvement in football is similar to Butler’s. He forged a successful career outside football as a lawyer before becoming treasurer at the JFF. Like Butler, Speid takes an interest in developing young players and boosting Jamaica’s profile on the international stage.


Bailey signing autographs at Phoenix (Craig Butler)

The result of the appeal was an indefinite coaching ban for Butler, forcing him to leave Stony Hill. While still under suspension, he formed the now-famed Phoenix academy, which operated around Kingston, before emigrating to Austria in 2010 with several of his most exciting prospects, including Bailey, while keeping the academy running through staff.

While Butler arranged trials and meetings for his players at over 150 European clubs, including Dutch giants Ajax, Speid became one of the most influential people in Jamaican football. Alongside an administrative role with the JFF, he became Cavalier FC’s head coach and chairman in 2016 and won the Jamaican Premier League in 2021.

With Spied’s power and influence in the JFF, Butler has publicised his suspicions that he has obstructed the international pathway for Phoenix players. Bailey, for example, won the under-13s, under-15s and under-17s KSAFA Player of the Year awards at 12 years old, but was not called up for Jamaica’s youth squads. This period coincided with Butler’s suspension, and in the aftermath of the court case, the JFF wanted to distance itself from Phoenix.

Ahead of the 2018 World Cup in Russia, Butler met with executives at England’s FA to explore the possibility of Bailey playing for England. The prospect was short-lived, as Bailey did not meet the requirements, as his British-based grandparents had been born in Jamaica. Bailey eventually committed to Jamaica in 2019 and has won 30 caps, scoring five goals.

It appeared relations had improved slightly, with Chelsea’s 18-year-old starlet and Phoenix graduate Dujuan Richards already on 10 appearances for the senior national team. However, seemingly out of nowhere, Bailey is now back where he started: disillusioned and unavailable for selection.

“From us the whole time, it was just (for) this camp,” Hallgrimsson said of Bailey’s suspension after the USMNT defeat. “I hope he will play for a lot of years for Jamaica. At the moment, he’s Jamaica’s hottest player, so I hope, but it’s up to him to decide that.”

That might be optimistic, as the heated climate shows no signs of cooling.

On March 17, Michael Ricketts, a close associate of Speid, won an election to serve a second full term as JFF president, defeating Butler-backed candidate Raymond Anderson.

The day before the election, Butler put a post on Instagram that reads, “The difference between humans and animals? Animals would never allow the dumbest ones to lead the pack.” In the accompanying caption, he described it as “the saddest day and the death of our country’s football, or the beginning of new hope”.

The politics of his father’s relationship with the JFF has clouded Bailey’s international career before it even began.

With three months remaining until their opening game of the Copa America against Mexico, Jamaica wait to see if their best-ever player will play in their most important tournament since that 1998 World Cup.



From tough start in Jamaica to trekking Europe with a dream – Leon Bailey’s remarkable rise

(Top photo: Matthew Ashton – AMA/Getty Images)

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