To Get to Maduro, Trump Went Through Puerto Rico

Aguadilla, Puerto Rico — Puerto Ricans have a saying — "El que se va para Aguadilla pierde su silla" — which roughly means that if you go to Aguadilla, you will lose your place in line.

Aguadilla, a small coastal city in northwestern Puerto Rico, is where my family and I drove Jan. 3 as we scrambled to get a flight back to the mainland after the American military operation in Venezuela disrupted travel for tens of thousands of people planning to fly in and out of the U.S. territory.

Aguadilla has also been witness to the dramatic American military buildup in the Caribbean that's made Puerto Rico an unexpectedly major part of the Trump administration's newly assertive posture in Latin America — and whatever comes next in Venezuela, following the U.S. capture of Nicolás Maduro.

After two weeks of visiting family over Christmas, we woke up in the middle of the night Saturday to make a flight out of Luis Muñoz Marín International Airport (SJU) near the territory's capital, San Juan, part of a metro area of about 2 million people. We had seen reports of bombings in Venezuela but didn't think it would affect our plans to fly back to Washington.

As soon as we arrived at SJU, that changed quickly: We found that the Federal Aviation Administration had closed the airspace to U.S. carriers. Puerto Rico sits roughly 500 miles north of Venezuela. We were stuck and the airport was quickly descending into chaos.

I should have known better.

While Puerto Rico became a major American naval hub during World War II, the U.S. military presence here has been far smaller since the end of the Cold War. Protests famously led the Pentagon to halt decades of U.S. Navy practice bombings in the Puerto Rican island of Vieques in 2001.

But as President Donald Trump ramped up pressure on Maduro in recent months, the U.S. has been sending in fighter jets, drones and other military hardware to the territory, making it the key U.S. staging ground in the region. Some of that hardware is at former bases like the airport in Aguadilla, a two-hour drive from San Juan and about a 30-minute drive from my hometown of Mayaguez. The naval station at Roosevelt Roads in eastern Puerto Rico has sprung back to life after closing in 2004.

The early Saturday operation — in which U.S. aircraft struck targets in Caracas and special forces captured and extracted Maduro and his wife — sent shock waves through the region. It also affected nearly 50,000 people planning to go through SJU, a connection hub to other parts of the Caribbean, during a busy holiday travel day. Airlines told some people it may take a week to get them home.

As we waited amid the growing cancellations and delays, hoping the FAA would open the skies, everyone was talking about the U.S. incursion just hours before, showing each other news stories and videos on their phones. Some were scoffing at what they saw as Trump's bellicose style. Others said good riddance to Maduro. A TV news crew eventually showed up. (As a former TV journalist myself, I wondered what took them so long.)

I overheard some people from the mainland U.S. commenting that Trump shouldn't leave Americans stranded abroad, and saw social media posts to the White House hoping for help — a reminder that many Americans still see Puerto Rico as some foreign land, nearly 128 years after the U.S. annexed the island following the Spanish-American war. The airspace remained closed for U.S. carriers.

Puerto Ricans themselves are obsessed with the territory's relationship with the United States, and discussion about the Trump administration’s military buildup has inevitably become part of the debate over its status. Puerto Rico has been a territory since 1898 and its residents U.S. citizens since 1917, but it seems everyone has a different view of how they fit into the American story.

Trump famously threw paper towels at people after Hurricane Maria slammed into Puerto Rico in 2017, destroying the electric grid and causing damage that is still being repaired. At times he blocked or slowed aid, pointing to the territory's corruption problems. But that doesn't mean Trump doesn't have MAGA fans in Puerto Rico.

Some Puerto Ricans have protested the military buildup. Others have welcomed it — many of them driving by the sites of military exercises to catch a glimpse.

Left-leaning politicians — including Juan Dalmau, a rising star among advocates of Puerto Rican independence — condemned the U.S. operation. Critics have long accused Dalmau of not distancing himself enough from Maduro and used that against him during the 2024 gubernatorial elections.

But Gov. Jenniffer González Colón, the pro-statehood Republican and vocal ally of Trump who beat Dalmau, cheered the president on, as local reporters pressed her about the impacts on tourism and the economy. González Colón was Puerto Rico's lone representative in Congress before moving to La Fortaleza, the governor's mansion.

"As Governor of Puerto Rico, I am proud that Venezuela will finally have peace without the narco-dictatorship of Nicolás Maduro and his cronies. The US Armed Forces and our Nation may continue to rely on Puerto Rico as a strategic partner in the mission to support our national security and bring stability to our hemisphere," González Colón said.

With Trump now pledging to “run” Venezuela for the foreseeable future — and the administration putting other regional leaders on notice about its sudden revival of the 200-year-old Monroe Doctrine — that partnership seems likely to grow.

Spain, which governed Puerto Rico for more than 400 years, considered the archipelago and the fortifications around Old San Juan key to defending its possessions around the Americas. The United States then used Puerto Rico's strategic location as part of its defense of the Panama Canal and to cement its preeminence in the hemisphere.

Some Republicans like Sen. Mitch McConnell have scoffed at the idea of Puerto Rican statehood. Trump is said to have talked about selling or trading the island in the past. But the president's geopolitical posture may have led him to reconsider any animosity. It also helps the territory has a pro-Trump governor.

Our San Juan flight finally canceled, the Uber driver who took us back to our place there, for one, said Maduro should have given up earlier. He predicted weeks of instability.

Luckily, after hours of searching, we found a flight from Aguadilla. We rented a car and raced there for a middle-of-the-night flight to Newark. We then drove down to our home outside Washington.

While I had seen the growing military presence throughout the island myself — at the airport in Ponce, a city in the south, I caught sight of military aircraft parked near the main terminal, for instance — I hadn't made it to Aguadilla to see the drones my dad kept telling me about. But I think I saw one in the darkness as our airplane prepared to take off at around 4 a.m. Sunday.

And as it turned out, we just missed Maduro himself.

As many Puerto Ricans suspected, the former Air Force base at Aguadilla was his first stop on American soil after U.S. special forces captured him in the dead of night and ultimately flew him to New York to await trial in a Brooklyn jail on narco-terrorism and drug-trafficking charges.

The giveaway? The photo that Trump shared on social media of a blindfolded, handcuffed Maduro showed him holding a bottle of what appeared to be Nikini brand water — widely available in Puerto Rico.