Steve McClaren went viral ahead of his first game in charge of Jamaica’s national team in September 2024 when he used a popular local slang “seal it up.” Ironically, it was his own fate that ended up being sealed after failing to secure qualification to the FIFA World Cup.

The Englishman returned home to Yorkshire on Wednesday, a day after solemnly reading from a two-page handwritten statement in his final press conference following the Reggae Boyz 0-0 draw with World Cup-bound Curacao at the National Stadium in Kingston.

His 475-day tenure, which saw him fail to win 12 of his 23 matches, ended with taking no questions from the media and was verbally abused by fans on his way out of the National Stadium in Kingston. In the tunnel shortly after McClaren’s departure, a frustrated Jamaica Football Federation (JFF) President Michael Ricketts, facing more than US $3 million ($480 million) in expenses for the final round of Concacaf World Cup Qualifying, told the Jamaica Observer that he wished he had fired him sooner with the team now forced into a last-chance bid for qualification through March’s inter-confederation play-offs.

It was a remarkable shift as just a year earlier, Ricketts told the Observer that the pair had “an excellent relationship” and was amazed by McClaren’s “warm personality.”

So how did it get to this stage?

On July 31, 2024, McClaren was selected by the Jamaica Football Federation’s (JFF) technical committee, led by now interim Head Coach Rudolph Speid, out of nearly 40 candidates who applied for the vacant position following the resignation of Heimir Hallgrimsson, who left for the Republic of Ireland national team.

It was a shock to many on the island as the former England manager had been part of the Manchester United coaching staff that won the FA Cup two months earlier.

Laurie Whitwell, Manchester United reporter for The Athletic believes McClaren’s decision to depart was driven by his desire to have more control after the club virtually added Ruud Van Nistelrooy and Rene Hake to Erik Ten Hag’s backroom staff.

“Steve was given a different role that was more peripheral really so I think he felt that he wasn’t necessarily as involved as he perhaps was previously and he would like to be in future,” Whitwell told the Observer. “He was influencing a little bit of the tactics at the end of (the 2023-24) season when they switched to 4-2-4 and certainly in the FA Cup final and that was what produced the performance and result against Man City at Wembley.”

“I think the club definitely would have kept him if he’d wanted to stay, but I think he felt that it was the right time to go. He was thinking, ‘Okay, this could be a real opportunity for me to take the team to the World Cup’.”

On August 8, 2024, at his first-ever press conference, McClaren, flanked by JFF leaders including Ricketts and Speid, made it known that his main objective was to lead the team to the 2026 showpiece. However, he raised a few eyebrows when he said he would remain in England instead of living in Jamaica, something that his predecessor Hallgrimsson did.

It was highlighted again last week by Craig Butler, the agent of Reggae Boyz Leon Bailey and Dujuan “Whisper” Richards.

“Him don’t feel it like how all of us feel it,” Butler told the Observer. “He gets up, goes on a plane, goes to his home and he’s happy and looks for the next job.”

But at the time, the JFF felt it could be an advantage. Not only would it eliminate an additional expense of accommodation costs but it would also allow him to stay connected with Europe-based players while actively identifying and recruiting new talent with Jamaican heritage.

The recruiting, though, would ultimately lead to friction.

Sources have said that McClaren had a bias towards the England-born players, which led to several of the team’s home-grown and local-based players at times feeling aggrieved. The players didn’t have any known personal issue with each other but there was often a disconnect.

McClaren, in press conferences for nearly a year, consistently said he was always looking for the best players which meant his recruitment drive knew no limits. “There’s never a cut-off. We’re always looking for the best players, players that can improve our team, players that can improve our squad,” he said.

Rico Henry, Mason Holgate, Isaac Hayden, Bailey Cadamarteri, Rumarn Burrell, Isaac Hayden, Tyreece Campbell, and Malik Mothersille all made their debuts under McClaren in a squad that already had a strong England-born presence. Several other players have been pursued including Marseille forward Mason Greenwood, who declined a call-up before the start of the World Cup Qualifiers, despite receiving his Jamaican passport.

One respected Jamaican coach, who has won multiple titles at the senior and youth levels including the Jamaica Premier League, told the Observer that he stopped going to home games because “he couldn’t recognise the team,” referencing the number of England-born players.

Sources have said that, despite McClaren’s praise of the Jamaica-born players in the public, his actions towards them, particularly regarding team selection, didn’t show such.

Several local stakeholders were also concerned about the limited involvement of Jamaica Premier League (JPL) players. Although McClaren held a local training camp in February which featured 25 JPL players, only midfielder Jahshaun Anglin saw any playing time in the World Cup Qualifiers, with just 29 minutes. Mount Pleasant goalkeeper Tafari Chambers made every match-day squad but never featured.

McClaren started to see his stock fall in the eyes of the JFF at the end of last June. Jamaica were seen as a top contender for the Concacaf Gold Cup but crashed out in the group stage for the first time since 2009. The Observer understands that strong consideration was given to sacking him but was ultimately given grace due to decent performances in the Unity Cup against Trinidad and Nigeria last May, as well as a convincing 3-0 win over Guatemala in the second round of World Cup Qualifying.

“He would have done well in patches,” Ricketts told the Observer last week.

McClaren survived the axe and got additional support from Speid who, after months, caved in and accepted to be his technical advisor, weeks before the start of World Cup Qualifying. McClaren was impressed by Speid’s technical knowledge as well as the performance of his club Cavalier FC in the local league and regional competition.

“Me and Coach McClaren work very well together, I trust him and he trusts me — I think it’s a good partnership in my mind,” Speid told the Observer last August.

With the addition of Speid and former Wolverhamption Wanderers assistant manager Ian Burchnall, McClaren felt more equipped heading into the World Cup mission.

Despite missing key players like Leon Bailey, Demarai Gray, Ethan Pinnock and Captain Andre Blake, Jamaica beat Bermuda and Trinidad to be two wins away from qualification with four games to spare. A win against Curacao in their next game would have meant they could have sealed the deal against Bermuda at the National Stadium in October.

However, the 2-0 defeat away to Curacao, which saw them fall to second in the group, was almost the writing on the wall. A senior JFF official, a source said, believed McClaren would have been fired immediately after the full time whistle had former president the late Captain Horace Burrell still been in charge.

But after hammering Bermuda 4-0 in Kingston days later and seeing Curacao draw with Trinidad on that night, McClaren would virtually silence the noise around his future as he entered the November window, needing just a win against Trinidad and a draw against Curacao.

That wouldn’t be the case. Jamaica drew 1-1 in Trinidad seeing them lose control of the group with ten points as Curacao were simultaneously thumping Bermuda 7-0 to go top with 11.

A move that was questioned by both the team and supporters was the exclusion of Shamar Nicholson from the game, who McClaren called the “best striker in the Caribbean” days earlier.

McClaren said he wanted to protect the 28-year-old, the country’s second all-time goalscorer with 21 goals, for the final game against Curacao, because he risked suspension if he received a yellow card. He also said the same of Ian Fray and Dexter Lembikisa.

McClaren said he informed the players of the decision and they agreed but privately, it was viewed as puzzling, knowing a win against Trinidad would have taken some of the pressure off against Curacao.

On the day of the Curacao game on Tuesday, where more than 35,000 fans turned up to witness the team qualify, a source said McClaren didn’t look very confident heading into the game.

However, it was understandable, as the burden of ending a 28-year World Cup drought and the hope of inspiring an island amid significant recovery from Hurricane Melissa weighed heavily on his shoulders.

The final whistle did nothing but add to the weight as Jamaica failed to get the win they needed, leaving an entire nation crippled by shock and despair.

The post-match press conference started later than in previous games as McClaren informed the players and the JFF that he would be resigning while also preparing his statement to the media. In it, he thanked the people of Jamaica, but the feeling was not mutual as the disappointment of Jamaicans would be long lasting.

While many, including former Reggae Boyz target Troy Deeney, have questioned the timing of McClaren’s resignation before the inter-confederation play-offs, it wouldn’t have mattered as sources confirm he would have been fired the day after.

It’s the second time in McClaren’s career where he’s faced major scrutiny at the international level after failing to qualify England for Euro 2008. Jamaica was his first head coach job in five years, after being sacked by Newcastle United, Derby County, and Queens Park Rangers between 2015 and 2019.

Given his track record and the condition of his ankle, as reported by Whitwell, McClaren may find it hard to attract top jobs.

“Maybe he could do a head coach role at another nation but would there be nations out there that would want him given this one wasn’t a successful campaign?” said Whitwell.

The Reggae Boyz now turn their attention to their final chance of qualifying for the World Cup in March and they’ll hope to get up to “Speid”.

Reggae Boyz Head Coach Steve McClaren looks on during Tuesday night’s final-round World Cup qualifier against Curacao at the National Stadium in St Andrew. McClaren announced his resignation after the game ended in a goalless draw, throwing the Jamaicans out of automatic qualification for next year’s tournament. Garfield Robinson

Reggae Boyz Head Coach Steve McClaren (right) issues instructions to members of Jamaica’s national senior team during a training session at the National Stadium on September 5, 2024. Photo: Garfield Robinson

From left: Greg Leigh (head down), Demarai Gray, Bobby Reid and Tafari Chambers saddened on the Jamaican bench after failing to automatically qualify for the 2026 FIFA World Cup. They drew 0-0 with World Cup – bound Curacao on Tuesday, November 18, 2025 at the National Stadium. Garfield Robinson