Manager Winfried Schäfer's Long, Winding Road to Jamaica

A little over 11 months ago, Jamaican soccer had the best night in its history. Playing in Atlanta, the Jamaicans stunned the U.S. National Team, 2-1, to advance to the final of the Gold Cup.

In that moment of jubilation, Jamaica coach Winfried Schäfer wrote that it was one of the best moments of his long career.

+40y in Football, saw it all, but believe me I'll never forget this night — Winfried Schaefer (@WinniSchaefer)July 23, 2015

Even though Jamaica would ultimately lose the Gold Cup final to Mexico, the victory over the U.S. still hasn't lost its significance. Sure, it was just a Gold Cup semifinal, but that game had Jamaican fans dreaming of bigger things.

"It was very, very important for the small island, (even though) the result is not very, very important," Schäfer told VICE Sports. "Our players played and fought for Jamaica. This was very, very good. The players were very motivated."

Now Jamaica is back in the United States, this time for the Copa America Centenario. With a date against fellow Group C team Mexico looming, the Reggae Boyz have an opportunity to avenge their Gold Cup loss.

The atmosphere surrounding the Jamaican team has changed since their last tournament appearance in the U.S. After a troubling start to World Cup qualifying last year, a Jamaican newspaper declared that Schäfer was "drunk" from the Gold Cup performances; as it stands now, the Reggae Boyz likely have to win their next two matches to advance in qualifying. Schäfer's Copa America experience hasn't been much better: he was ejected from his team's first-round game against Venezuela on Sunday, following a red card to midfielder Rodolph Austin. He watched from the stands as Jamaica lost, 1-0, to the worst team in a tough group, which also features Uruguay.

Such has been the career of Winfield Schäfer, whose pale skin, thick glasses, and flowing silver hair give the aura of a mad scientist on the sidelines, not a manager. His fortunes have oscillated between the highest of highs and the lowest of lows.

The highs have been pretty great, and Schäfer has, at times, been considered one of the better managers in the game. In the 1990s, he took Karlsruher SC, typically a second-division team in the Bundesliga, to places it had never seen. His team was runner-up for the German Cup in 1996, and made it to the UEFA Cup (now the Europa League) in 1993-94, stunning top-ranked Valencia, 7-0. He told German newspaper Bild years laterthat he was offered the head-coaching job at Bayern Munich in 1994 but turned it down.

Then, things went downhill. Under new ownership, Karlsruher tanked, and headed toward relegation. So Schäfer left for Karlsruher's rival, Stuttgart, where he lasted just one season before being fired. He then took a job with second-division squad Tennis Borussia Berlin, which promptly got relegated after one season.

Just four years after bringing Karlsruher to new heights—and being sought after by the best teams in the Bundesliga—Schäfer had coached his last game in the league. The next decade would take him to Cameroon, the UAE, Azerbaijan, and Thailand managing for clubs and countries. Like his experience in Germany, he alternated between successful stints and cancelled contracts. It was a stunning development for someone who had turned down a managerial job at one of the biggest clubs in the world.

That fall has come to define Schäfer in Germany, but in the larger picture he can't be seen as a great or a disappointing coach. He's just a certain kind of coach: a great team-builder who's still looking to break through, even at 66 years old.

By all accounts, Jamaica should not be competitive with other teams in the Americas. As Schäfer put it, it's "a small island against big, big, big states," and some of the best teams in the world. "When we see the States and the stadium and training facilities of Jurgen Klinsmann, it's a football paradise," he said.

"Here in Jamaica, we don't have a lot of money," Schäfer continued. "All the money is coming from the success of the team. I told our president, everybody—all (the) people from football, the coaches—all eat from the success of the team.

"It's very difficult. We always talk about money, what we can do to save money."

Nevertheless, expectations have been raised for the Jamaicans, who haven't reached a World Cup since 1998, because Schäfer gets results despite those limited resources.

There was the 2-1 win over the United States, of course, but also a win against Chile, two draws against 2014 World Cup quarterfinalist Costa Rica, and hard-fought, close losses against Argentina, Uruguay, and Mexico. This is Schäfer's specialty: take a team that has no business being successful and bring them to the edge of glory.

"This is hard work," he said. "We have no Messi, we have no Ronaldo, we don't have Neymar. We have a very strong team, and team-building is what I like."

In Jamaica, Schäfer hopes to emulate Klinsmann's strategies in the U.S., like finding internationals in the best leagues to join his team. He already has had some success with that, including recruiting Leicester City star captain Wes Morgan for the Jamaicans in 2013.

"I'm looking for young players," he said. "I'm looking for the players from England. Wes Morgan, for three years he was only a player in Leicester, and this was one of the best defenders in England.

"We need more players from England, but we need more players from our talent (pool) to go out to MLS or to Europe, like Klinsmann sent all his players out from the States. That is what we want; it is the future."

So far, the results have been inconsistent. Jamaica, much like Schäfer's career, has followed not so much an arc but rather a sine curve, with triumphs greater than his club has ever seen and tribulations that make fans question his methods.

At 66 years old, Schäfer is still building. He said he hopes to go to England next and build a team there. No matter what happens with Jamaica, it's a good bet that he still has a few stunning results left in him. The question is whether he'll ever be more than that.