When it was announced that Puerto Rican superstar Bad Bunny would headline the 2026 Super Bowl halftime show, the news ignited a firestorm that was about far more than music or celebrity. As reported by The Latino Newsletter, the artist’s bold statement that viewers have “four months to learn Spanish” sent shockwaves through American pop culture. But beneath the surface, the uproar has laid bare the centuries-old tensions at the heart of Puerto Rico’s relationship with the United States—a relationship defined by colonialism, cultural misunderstanding, and a persistent struggle for identity.
To understand the current controversy, it helps to look back. Puerto Rico’s complicated status as a U.S. territory began in 1898, when the United States invaded the archipelago during the Gilded Age presidency of William McKinley. According to a recent letter published in The Press Democrat, McKinley’s tenure marked a new era of American imperialism, with the U.S. seizing Hawaii, Puerto Rico, Cuba, and the Philippines. The Philippine-American War alone cost 200,000 lives before the islands became a U.S. colony. In Puerto Rico, the aftermath was different but no less profound: the island became an “unincorporated territory,” a polite term for a colony, and its people found themselves in a legal and cultural limbo that persists to this day.
The U.S. Supreme Court’s 1901 Insular Cases, as highlighted by The Latino Newsletter, cemented this ambiguous status. The rulings limited the constitutional rights of Puerto Ricans, labeling them “alien races” and “savage tribes.” This meant that Puerto Rico belonged to—but was not truly part of—the United States, a colonial experiment that has failed to erase Puerto Rican culture, language, or national identity. The March 1917 Jones–Shafroth Act granted U.S. citizenship to Puerto Ricans, but it was a statutory citizenship, not constitutional, and thus could be revoked or altered by Congress at any time.
For many Puerto Ricans, the experience of being “American” has always been fraught. The Great Puerto Rican Migration between the 1940s and 1960s saw thousands move to New York City, lured by promises of opportunity. Instead, they encountered housing discrimination and were forced into crowded tenements in neighborhoods like El Barrio and Loisaida. As one elderly Puerto Rican woman recalled in The Latino Newsletter, “I remember when we couldn’t find housing. No one wanted us. Landlords wouldn’t rent to Puerto Ricans. We had to live in tenements, packed into slums, because we were not considered American enough.” Her words echo the persistent feeling of exclusion that has dogged Puerto Ricans for generations.
Fast forward to today, and those old wounds have been reopened by Bad Bunny’s unapologetic embrace of Puerto Rican identity on America’s biggest stage. The backlash—ranging from MAGA supporters incensed to learn that Puerto Ricans are U.S. citizens, to liberal “allies” who insist that Puerto Ricans should be accepted only if they act “American”—reveals a deep ignorance about the island’s history and status. As Myrta Vida, a New York-based Puerto Rican filmmaker, put it, “I’ve said it once, and I will say it one thousand more times: why aren’t Americans more ashamed of their ignorance of history and civics? Being proud of being American is not enough.”
Even within Puerto Rico, identity and political status remain deeply contested. The island is still divided over its future: Should it pursue statehood, independence, or some form of free association? The 2022 Puerto Rico Status Act, which called for a federally binding referendum on the issue, passed the House but never made it to the Senate floor. The debate is not just academic; it shapes the lives of millions. In the 2024 Puerto Rican elections, the pro-statehood Partido Nuevo Progresista (PNP) and Trump-supporting Republican Jenniffer González-Colón won the governor’s race with just 39 percent of the vote. Remarkably, independence candidate Juan Dalmau came in second with 33 percent—the first time in 70 years that a third-party candidate finished so high. Dalmau’s recent visits to Washington, D.C., underscore the growing momentum for change.
Meanwhile, the frustrations of daily life in Puerto Rico—an imposed fiscal control board, a fragile electrical grid, high costs of living, and rampant corruption—have only fueled calls for greater sovereignty. Many Puerto Ricans are weary of being treated as a colonial outpost or a playground for mainland tax evaders, as highlighted by the ongoing gentrification driven by Act 22 tax incentives. The sense of being “American, but not American enough” is a bitter pill, especially as the island grapples with the legacy of policies imposed from afar.
For some, the reaction to Bad Bunny is a microcosm of a much larger problem. The backlash from Trump’s America is overt and often vitriolic, but the assimilationist narrative from supposed allies can be just as insidious. Isabella Risa, a young Puerto Rican activist, told The Latino Newsletter, “The framing of him being part of the U.S. as some cover as to why we shouldn’t receive this hate is not only American exceptionalism at play… but it also neglects the entire point of the newest album. That we are a colony, and aren’t part of the U.S. but occupied by it.”
These tensions are hardly new. As The Press Democrat letter writer Tony White observed, the United States’ Gilded Age was marked by xenophobia, nativism, racism, and the use of military force to protect American interests abroad. “It’s déjà vu all over again: Corruption reigns, oligarchs rule, tariffs jumped prices, troops occupy cities, justice is denied, friendly neighbors are threatened, gunboats are sent to the Caribbean,” White wrote. The echoes of the past are unmistakable in today’s debates over Puerto Rico’s place in the American story.
For Puerto Ricans, the struggle is not just about legal status or political labels, but about dignity and recognition. As the iconic poem “Puerto Rican Obituary” by Pedro Pietri reminds us, generations have worked, endured, and contributed—“They worked / They were always on time / They were never late / They never spoke back when they were insulted.” Now, with Bad Bunny’s defiant performance on the horizon, many see an opportunity to reclaim their voice and challenge the stereotypes that have long defined them.
As the world watches the 2026 Super Bowl halftime show, the spotlight will not just be on the music, but on the unresolved questions of identity, belonging, and justice that have shaped Puerto Rico’s relationship with the United States for over a century. For many Boricuas, this is more than a performance—it’s a declaration that their story, culture, and language deserve to be heard, not just tolerated.