Wait. Let’s clear something up right away. There is no "President of Puerto Rico" in the way most people think.
When you hear about Trump speaking to the president of Puerto Rico, you’re likely remembering one of two things: a famous verbal slip-up or the complex, often messy reality of how the U.S. government interacts with its island territory.
See, Puerto Rico is a commonwealth of the United States. That means the President of the United States is the President of Puerto Rico. In 2017, during the absolute chaos following Hurricane Maria, Donald Trump made a comment about meeting with the "President of the Virgin Islands." He was, of course, the President of the Virgin Islands. He had actually met with Governor Kenneth Mapp.
People often conflate that moment with his interactions with Puerto Rican leaders. It’s a bit of a "Mandela Effect" in political news. Because the relationship was so tense, the details get blurred. But the actual human beings on the other end of those conversations were governors—specifically Ricardo Rosselló and later Pedro Pierluisi and Jenniffer González-Colón.
Why the President of Puerto Rico confusion matters
The confusion isn't just a funny trivia point. It’s basically the core of the political tension. When a U.S. President talks about Puerto Rican leadership, they are talking to a governor who has significant power on the island but zero voting power in Congress.
During his first term, Trump’s relationship with the island was defined by the aftermath of Hurricane Maria. You probably remember the video of him tossing paper towels into a crowd. It became a permanent Rorschach test for American politics. To his critics, it was the height of dismissiveness. To his supporters, it was a president being "unfiltered" and trying to help a crowd in a desperate situation.
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But the real "speaking" happened behind closed doors and via Twitter (now X). Trump frequently clashed with San Juan Mayor Carmen Yulín Cruz. He called her leadership "poor" and suggested that Puerto Rican officials "want everything to be done for them."
The Rosselló Years and the 2017 Fallout
Back in 2017, the governor was Ricardo Rosselló. Early on, the tone was actually quite professional. Rosselló was initially complimentary of the federal response, likely trying to secure the billions in aid the island desperately needed.
Then things got weird.
The death toll estimates jumped from 64 to nearly 3,000. Trump contested these numbers, famously tweeting that they were a plot by Democrats to make him look bad. This created a massive rift. When we talk about Trump speaking to the president of Puerto Rico (or rather, the governor), we’re talking about a period where trust completely evaporated.
- Aid Withheld: For a long time, billions in HUD (Housing and Urban Development) and FEMA funds were tied up in bureaucratic red tape.
- The "Swap": Former DHS officials later claimed Trump privately asked if the U.S. could "trade" Puerto Rico for Greenland because he viewed the island as "dirty" and "poor."
- The Oversight Board: The "Junta"—an unelected board managing Puerto Rico's finances—often stood between the President and the Governor, making direct communication even more difficult.
Fast Forward: Trump and Jenniffer González-Colón
By the time 2024 and 2025 rolled around, the landscape shifted. Jenniffer González-Colón, a Republican and long-time Resident Commissioner, became Governor in early 2025.
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She has always had a more strategic relationship with Trump. Even when the "island of garbage" joke was made by a comedian at a Trump rally in late 2024, González-Colón had to balance her outrage with the reality that she might need to work with a Trump administration.
When Trump speaks to her today, the conversation isn't about paper towels. It’s about the $100 billion plus in recovery funds that are still being spent. It's about the "Junta" and whether the federal government will finally allow Puerto Rico to manage its own wallet again.
Honestly, the "President of Puerto Rico" error is a perfect metaphor. It shows how easy it is for the mainland to forget that Puerto Ricans are U.S. citizens. If you don't know who the "President" is, you probably don't know that the people living there can't vote in the general election, despite being subject to the President's decisions.
What actually happens when they talk?
The interactions are rarely just "chats." They are formal readouts.
When Trump speaking to the president of Puerto Rico (Governor) happens, it usually involves the Federal Coordinator for Recovery. In 2025, Trump made moves to fire members of the fiscal oversight board, a move that local leaders had mixed feelings about. Some saw it as a path to sovereignty; others saw it as a recipe for financial chaos.
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Nuance is everything here.
Trump’s rhetoric often suggests a desire to "cut ties" or limit "handouts," yet his administration also oversaw the obligation of some of the largest FEMA grants in history toward the end of his first term. It’s a paradox. He complains about the cost while his agencies sign the checks.
Actionable Insights: Navigating the News
If you’re trying to keep up with the latest on U.S.-Puerto Rico relations, stop looking for a "President of Puerto Rico." It doesn't exist. Instead, keep your eye on these three things:
- The Governor’s Office (La Fortaleza): Watch how Governor Jenniffer González-Colón navigates the Republican party line while advocating for the island's unique needs.
- FEMA Obligation Reports: Don't listen to the "billions" quoted in speeches. Look at how much money is actually "spent" versus "allocated." There is a massive gap.
- The Status Debate: Every time Trump speaks to the island's leadership, the underlying question is: Statehood, Independence, or the Status Quo?
The next time a headline pops up about a meeting or a phone call, remember that the person on the other end isn't a foreign head of state. They’re the leader of 3.2 million Americans who are often caught in a political tug-of-war.
The best way to stay informed is to follow local outlets like El Nuevo Día alongside mainland news. You’ll quickly see that the "conversation" looks very different depending on which side of the ocean you're standing on.
Pay attention to the specific names—González-Colón, Pierluisi, Rosselló—and you'll have a much clearer picture than the people still searching for a "President" who was never there.