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Steve McClaren departed from an international position nearly two decades ago after England was unable to qualify for a major championship, specifically missing out on Euro 2008.
He certainly did not want to experience that level of despair once more.
Yet, here he found himself, deep within the National Stadium in Jamaica, grappling with the implications of a 0-0 draw against Curacao. While it marked a remarkable achievement for the small Caribbean nation, which is now the smallest to qualify for the World Cup, it symbolized a significant setback for the 'Reggae Boyz.'
Maintaining his composure just as he did following his failure with England, McClaren announced the conclusion of his 18-month role as head coach of Jamaica.
"I have committed my all to this position over the past 18 months," he remarked. "It has been one of the most rewarding experiences of my professional life to lead this team.
"However, football is driven by results, and tonight we have not met our objective of advancing from this group.
"It is the duty of a leader to take responsibility, make accountable decisions, and act in the team's best interests.
"After careful consideration and an honest evaluation of our current state and future direction, I have chosen to resign as head coach of the Jamaican national team.
"At times, the most prudent course of action for a leader is to acknowledge when new perspectives, fresh energy, and different ideas are needed to propel the team forward."
These statements conceal a substantial hit to McClaren's professional ego.
Having left a position as assistant to Erik ten Hag at Manchester United in the summer of 2024, McClaren was drawn to the opportunity presented by the Jamaican contract, especially since the leading Concacaf nations—USA, Mexico, and Canada—had already secured automatic entry to next year's tournament as co-hosts.
He had promised he would return following his difficult stint with England. On the international front, this was meant to be his chance.
Jamaica had never been in a better position to replicate the success of the 1998 squad featuring Robbie Earle, Fitzroy Simpson, and Frank Sinclair by qualifying for the World Cup for only the second time ever.
The journey, however, was not simple.
Initially, attempts to include Mason Greenwood in the lineup faced delays due to documentation issues. After the former Manchester United forward obtained citizenship in August, he turned down a call-up the next month, stating he was not ready to represent Jamaica.
In the days leading up to the game, McClaren had been anxiously awaiting the availability of another player born in the UK, Brentford defender Rico Henry, who was only given the green light to make his debut just hours before Thursday's draw against Trinidad and Tobago.
It was expected that Michail Antonio would also join his team, but the former striker for West Ham has not participated in any competitive matches since he played for Jamaica during their Gold Cup run last summer, which marked his return after a serious car accident six months prior.
Additionally, there is the challenge of competing in a Confederation where conditions can shift dramatically from frigid temperatures and snow to intense heat within the duration of a flight.
"These past 18 months have been tough - extremely tough," McClaren remarked. "I’ve had to adapt and learn quickly."
"My experience with Concacaf football has been unlike any other. Football in the Caribbean is distinct from that in Central America, which in turn differs from North American football. This is something I've never encountered before."
Looking back, the last-minute equalizer that Jamaica conceded to Trinidad and Tobago last week turned out to be significant, as it resulted in Curacao needing only a draw in the final game.
The exhilarating pre-match enthusiasm from a full house at Kingston's National Stadium, filled with cheering and vuvuzelas, quickly transformed into tension as Jamaica struggled to take control of the game in the first half and instead experienced a difficult night with only one shot on target.
They struck the woodwork three times during a frantic second half. An injury-time penalty appeared to be their salvation, but the video assistant referee ruled otherwise.
Even a motivational speech from Usain Bolt, arguably Jamaica's most celebrated athlete, could not lift their spirits.
Jamaica still has an opportunity for qualification; however, the odds are increasingly unfavorable in a six-team mini-tournament in Mexico, where they must secure victories in two matches. This will culminate in a final against either DR Congo or Iraq.
For McClaren, there is not the same cushion.
Ironically, after losing his position with England, he found solace in the Caribbean while vacationing in Barbados.
Now, he is departing the region after failing to provide relief to a populace still grappling with the aftermath of Storm Melissa, unable to create the joy he fondly described as the Jamaican smiles.
While McClaren has experienced success as a club manager, his international memories are overshadowed by significant regrets.
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