Anguilla (pronounced Ang-WHEEL-Ah) is one of the first on the list of FIFA’s 209 members according to alphabetical order. But in the world ranking, a list driven by the numeracy of results and intractable goals-for and against columns, the Caribbean island teeters in the shadows of ignominy, second-bottom globally ahead of only the Himalayan kingdom of Bhutan.

“It means nothing to me,” their coach Richard Orlowski told FIFA.com about the country’s lowly rank of 208th. “We’ve had some bad luck in the past; there’s no denying. But now we play in the present. So whoever says that Anguilla doesn’t have a chance, I say to them: 'this is football and anything can happen'.”

The tiny island, at the northern edge of the Leeward Islands, is an earthly paradise. It sways to ancient and mythical maritime rhythms and exudes a seductive calm. But on the football pitch, Anguilla suffers. They have only a rag-tag amateur league to draw their national team and they famously lost 16-0 over two legs to El Salvador in qualifying for the 2010 FIFA World Cup South Africa™. Anguilla has, in fact, played only four qualifiers in their history, and they’ve lost them all by a combined score of 33-2.

Anguilla draws many well-heeled tourists to bask on its beaches and bobble in the crystal water of its bays. But Orlowski is a man on a mission. He’s accustomed to travel, but they are the hard kinds of miles. He is no tourist. He began life as Ryszard Orlowski and fled to Austria from his native Poland in 1984 to escape political repression, before being granted refugee status in the United States and establishing a home in New York City. He now lives in Pennsylvania and had a successful stint as assistant coach of Nepal a few years ago, helping the Himalayan side earn a famous win against India and climb a small stretch of the lower reaches of the world rankings.

Orlowski was a striker in his native Poland, playing for a succession of unheralded clubs like ZKS Gofabet and ZKS Piotrcovia-Piotrkow Tryb. And much like he did in Kathmandu, he has already got the locals in Anguilla on his side with a famous win, one a long time in the making. Since taking the reins in February, he presided over a pair of victories against British Virgin Islands and another against St Martin. These were the first wins for Anguilla in the space of 14 years and casual soccer fans on the island have taken notice.

“I want to make this a winning team by challenging the players to believe in themselves,” he said, his English still broken and revealing echoes of his native Poland.

Facing the abyss
But Orlowski’s next challenge is his biggest, and it comes with consequences. Early next week, Anguilla play their fifth-ever World Cup qualifier, against Nicaragua. The first leg is in Managua and the second back home on the island in The Valley. Anything less than a pair of wins could see them fall to dead last in the world ranking, as Bhutan beat Sri Lanka twice last week. Anguilla are in danger of taking over the unwanted mantle of world’s worst team.

“We’ve worked hard for the past five weeks,” added Orlowski, who has brought increased professionalism and tactical awareness to the island’s football, locating young, unknown players from the seven-team domestic league to form the crux of his squad. “I told the players to imagine that this game is just another friendly. Hopefully it will calm their nerves.”

Nicaragua are no giants by any means, but they are 23 places above Anguilla and have a population of six million compared to Anguilla’s 14,000. Orlowski knows better than anyone that his team are strictly amateur, hoping against hope. But his admiration of his team’s sacrifices on this hopeful crusade is palpable. “It may be a small island, but these guys have the biggest hearts I’ve ever seen,” said Orlowski, whose team is comprised of construction workers, bankers, teachers and boat builders. “They leave work early to train and some even risk getting less pay. I feel so much pride when I see them come out on the pitch, how much they juggle in their lives.”

If Anguilla come up short next week, the world would not end. The players would return to school, or take up their sledgehammers at work. Maybe they would fall to the bottom of the global pecking order. But, in truth, there are worse places than sunny Anguilla to be last.

But do not try selling that generous romanticism to Orlowski. “We’ve won three games now and winning is contagious,” he said, defensive of his side’s chances. “Play our football and we will succeed.”