If Not Now, Then When For Jamaica?

If not now, then when? That’s the question being asked by many Jamaicans after the Men’s National Team’s complete failure to qualify for the 2026 World Cup this summer. Not having to play the USA, Canada, and Mexico in qualifying made a potential pathway to the recently expanded tournament arguably easier on paper. However, in games like these there are no “easy” games or walkovers, including a team like Curaçao, which has been developing well over the past few years, to the surprise of many Jamaicans. Even more embarrassing than the on-field failure is the off-field circus led by Michael Ricketts and company, who are quoted as saying “things never went our way”, suggesting a clear blindness to the underlying systematic issues that have allowed Jamaica to now be labeled as one of the most disappointing and underperforming national teams in the world by many overseas media outlets.

For the past few years, Jamaica has felt like a national team that could — and realistically should — be a consistent Top 5 team in CONCACAF. It feels as if we are constantly on the verge of achieving that. One set of poor and inconsistent results inevitably leads to a “new” project — one that is often nothing more than a reflection of the previous one, creating the illusion of starting over. The cycle repeats itself like a carousel at a circus, constantly in motion, yet ultimately going nowhere. These outcomes are not driven by “things not going our way”, but by the absence of an efficient and stable system off the field. You reap what you sow.

Whether local talents, dual-nationals from the diaspora, or a blend of both within the national setup, there has long been a need for efficient organization and strategy within the Jamaica Football Federation to properly support the national team. The logistical and financial mismanagement that has plagued the federation for years is now being highlighted by major international outlets such as The Athletic, CBS Sports, and The Analyst — not a good look. When a federation is unable to pay staff, organize travel properly, and invest in basic performance infrastructure and technology, it becomes impossible to build a consistently performing team regardless of the players and the potential. Chaos at the foundation inevitably leads to instability and embarrassment on the field, not helped by disciplinary issues with players, which reflect the lack of discipline and professionalism that plagues today’s society in Jamaica.

What follows these failures is exactly where we are at this moment in time — a reactive illusion of resetting the football “project”. However, without structural and financial restructuring of the federation, there is no new project, only repetition. A new coach and a new pool of players may emerge in the coming months, bringing with them the hope of a “new era” for the federation leadership. However, without restructuring and stability, direction, and continuity, the same cycle will simply repeat itself, something many Jamaicans are now fully aware of.

In addition to financial and organizational restructuring, a clear long-term operational strategy for the federation must be defined and followed. This strategy is not referring to a on the field distinct tactical identity, which is not a viable solution for more reasons than one. What this operational framework should define is how the federation intends to operate over a sustained number of years — from organizational culture, to how technical staff are selected, to how both local and diaspora players are integrated into the national setup. For years, Jamaica has flipped between local and foreign coaches, while the player pool itself shifts too frequently from camp to camp. Once again, we find ourselves at a familiar point, with President Ricketts suggesting a return to a local coach. Yet beyond names such as Miguel Coley, there are essentially no candidates with the profile that are even worthy of being in discussion to lead the national team. This is exactly why Jamaica constantly is recycling the same coaches and same names across its different teams under the federation with no new coaches and faces coming into the picture. Names such as Wendell Downswell, Theodore Whitmore, Aaron Lawrence and more have been and still are stuck as coaches under the federation since the days of post-1998. This is exactly another reason why Jamaica is unable to progress and innovate and is still stuck fantasizing and trying to replicate the days of 1998. But replication is not what must happen. Progress must and for progress, the federation must first decide how it wants to function before determining anything else.

This lack of operational direction, structure, and efficiency is one of the key reasons why barks from individuals such as Craig Butler for a single, clear tactical identity are misplaced without proper context — focusing on an idealistic and simplistic solution to a much deeper and complex problem. If the environment is inefficient, unsustainable, and unable to support its product, there is no way a single identity can be created and sustained. Even more importantly, modern football is no longer conducive to teams built around one rigid identity. Today’s most successful teams are tactical chameleons — teams that are able to adapt, adjust, and evolve depending on what each opponent and game requires. For example, teams such as Argentina in the 2022 World Cup and Italy in the 2020 Euros demonstrated this ability, and without it, they likely would not have won those tournaments. A single tactical identity risks developing players with a limited number of solutions in a dynamic, unpredictable game that demands constant adaptation, where a single moment can define the outcome.

Furthermore, where countries such as France, Spain, the Netherlands, and Germany consistently produce elite-level players, Jamaica realistically does not have the infrastructure, knowledge, or supporting professional club system required to do so. Without these foundations — strong academies, consistent development pathways, and a functioning league system — developing players within a defined tactical framework becomes extremely difficult.

The ability to do this requires constant innovation, investment, and learning — three areas in which Jamaica is not well positioned at this time. Take, for example, England. Despite having the best league in the world and significant resources, they struggled on the international stage for years before their recent improvements. The cause? A degree of geographic separation from mainland Europe, combined with an arrogant mindset towards learning and innovation in the game. The mentality of “we invented football, no one can tell us how to play it” left England lagging behind in high-performance development, technology, tactical evolution, psychological preparation, and coaching education. One clear indicator of this is the limited number of elite English coaches, even within the Premier League itself. That gap has led to increased reliance on foreign expertise at the highest level, which also reinforces why Steve McClaren was never the right solution for Jamaica.

With limited resources, geographic distance from leading football nations, and a federation leadership that appears comfortable with the current state of operations, Jamaica is not in a position to consistently learn, invest, and innovate at the level required.

If not now, then when? The answer is simple — seemingly not for now. Not until the federation becomes open to change, and decides to operate in a stable, organized, manner so that it is capable of supporting the national team at a basic level. Until then, Jamaica will continue to repeat the same cycle — new ideas, new faces, but the same outcome.