CONCACAF World Cup Qualifying Will Never Be the Same

So I'm Savoring Every Moment of the Octagonal

The view writing from my balcony Monday morning

IRISH TOWN, Jamaica — I can’t tell you how much I’m going to miss the men’s CONCACAF World Cup qualifying tournament in the future. The current format has more or less stayed the same since qualifying for World Cup 1998: The USMNT has been part of a months-long home-and-away tournament involving five—or, this time, seven—other teams in the region.

The games truly matter, and if you’re someone who follows it closely—I’m covering all 14 qualifiers on-site—you also get a memorable travel experience around some of the most gorgeous parts of North and Central America and the Caribbean.

But I’m treasuring every moment this time around because it’s likely never going to be the same again for the USMNT. The U.S., Mexico and Canada are co-hosting World Cup 2026, and while FIFA hasn’t yet made it official that the hosts will receive automatic bids, everyone assumes that will be the case. So the U.S. almost surely won’t need to qualify in the next cycle. 

What’s more, the men’s World Cup will expand from 32 to 48 teams in 2026. So even when the U.S. has to qualify for World Cup 2030, the challenge will be infinitely easier if CONCACAF sends, say, a guaranteed six teams to the World Cup instead of the current three. There just won’t be that much at stake for the USMNT.

And don’t get me started on what happens if FIFA gets its way and institutes World Cups every two years (World Cup 2028?), which wouldn’t leave time to have a meaningful regional qualifying tournament like this one.

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So I’m savoring everything on these trips. In El Salvador, it was the pre-match fireworks that extended into the game’s first five minutes and the PA system playing Live Is Life, the soundtrack for Diego Maradona’s most memorable warmup of all time. In Honduras, it was the amazing pre-game pupusas from a food truck that I demolished on a paper plate, the Hondureña who made them smiling at my smiles. In Panama, it was doing a pre-game Twitter Spaces from the stadium in two languages with my friend Nicolle Ferguson.

And the games in the U.S. have been a blast, too, from Nashville to Austin, from Columbus to Cincinnati. I’ve been blown away by all the new MLS stadiums, and the communal energy at those games has been off the charts. The convincing U.S. win over Mexico took it to a new level. There hasn’t been this much excitement around the USMNT since World Cup 2014 in Brazil.

That brings us to Jamaica, which might be my favorite trip of the bunch. The game is in Kingston, which isn’t like the tourist destinations on the other parts of the island like Negril and Montego Bay (where most of the American Outlaws are staying, quite reasonably, before taking a bus to and from the game). 

Not sure if I’m coming back from Jamaica

My favorite place to stay here is a 45-minute drive into the Blue Mountains above Kingston. It’s a boutique hotel (that’s not overly expensive) called Strawberry Hill. Every morning I brew some local coffee, go out on my terrace with a ridiculous view overlooking the city and sit down to write. On Sunday morning, the beautiful sounds of singing from a nearby church service filled the air. This morning the sounds are coming from the roosters in the neighborhood. You couldn’t ask for much more. There’s a reason I’m staying here an extra day after the game and not returning to New York until Thursday.

This isn’t a paid ad for Strawberry Hill, but if you ever come to Jamaica, consider taking the road less traveled—which is to say, narrow roads with crazy hairpin turns up into the mountains—and check it out. The place is owned by Chris Blackwell, the Rock & Roll Hall of Fame producer who co-founded Island Records and brought to the global masses Bob Marley, U2, Steve Winwood, Grace Jones, Melissa Etheridge and a bunch of other artists. 

Chris Blackwell and Island Records brought Bob Marley and U2 to the masses

As you might expect, great music is playing all day long at the bar and restaurant here, and the walls of the place are covered in Blackwell’s classic music-themed photographs and, in one special room, gold and platinum records commemorating millions of albums sold. 

Strawberry Hill is where Marley came to recover after being shot in 1976. And you never know who you might meet here. One day when I was having a Red Stripe or three at the bar before a qualifier in 2013, I got into a fun soccer conversation with a guy who was clearly a fan of the game. It turned out to be Captain Horace Burrell, the longtime president of the Jamaican Football Federation. 

The Captain, as most people called him, had a fascinating life. He had served in the military for decades (hence: Captain), had fought on the U.S. side in the 1983 invasion of Grenada and had become wealthy as the proprietor of the Captain’s Bakery chain across Jamaica. In soccer politics, the Captain was an ally of both the notorious Jack Warner and U.S. Soccer. He served a six-month suspension from FIFA in 2011 for his role in the Mohamed bin Hammam CONCACAF bribery scandal.

The Captain was what I’d call a charming rogue, in the same way that the former Mafia don Anthony “Fat Tony” Salerno was described by the old New York City columnist Murray Kempton. The Captain served his time with FIFA—he got caught and deserved to—and he eventually came back stronger than ever, playing a major role with then-U.S. Soccer president Sunil Gulati in 2016 in swinging the FIFA presidential election from Bahrain’s Sheikh Salman to Gianni Infantino in the final round of voting.

The Captain passed away from cancer a year later. He was a figure in the grey areas of FIFA politics. But I’ll still remember having beers with him that day and getting a sense of what he was about. In the military he had picked up aviation skills. So I shouldn’t have been surprised when he left Strawberry Hill that day in 2013 in his helicopter.