Podcast Summary: Letters from an American

Host: Heather Cox Richardson (read by Michael Moss)
Episode Date: February 9, 2026
Release Date: February 10, 2026
heathercoxrichardson.substack.com

Episode Overview

This episode delves into the historical and political complexities underpinning Puerto Rico's status and relationship with the United States, sparked by current events: Bad Bunny's record-breaking Super Bowl halftime performance and the ensuing political discourse questioning his "American-ness." Through the lens of U.S. colonialism, economic motives, Supreme Court decisions, and cultural identity, the episode provides context for why Puerto Rico's status remains contested and misunderstood.

Key Discussion Points & Insights

1. Bad Bunny's Historic Performance and Its Backlash

[00:05-01:00]

• Bad Bunny, the Puerto Rican singer and record producer, performed the most-watched Super Bowl halftime show in history (135 million+ live viewers).
• He recently became the first artist to win a Grammy for Album of the Year with an album recorded in Spanish.
• Despite his success, some right-wing critics argued Bad Bunny was "not an American artist."
  • “In fact, people born in Puerto Rico are American citizens. But Puerto Rico has an odd relationship with the United States government, a relationship born of the combination of late 19th century economics and US racism.” [01:05]

2. Origins of the U.S.-Puerto Rico Relationship

[01:10-04:00]

• The rise of monopoly trusts in the late 1800s, especially the Sugar Trust (American Sugar Refining Company), influenced U.S. territorial expansion.
• The McKinley Tariff (1890) incentivized domestic sugar production, prompting actions to control sugar-producing territories like Hawaii and Puerto Rico.
• The annexation of Hawaii, motivated partly by sugar interests, set a precedent for acquiring other islands during/after the Spanish-American War (1898).
• Treaties post-war transferred control of Cuba, the Philippines, Puerto Rico, and others to the U.S., all with valuable sugar markets.

3. Legal and Racial Foundations of Colonial Status

[04:05-06:30]

• Historically, new U.S. territories were to be fully incorporated as states (per the Northwest Ordinance of 1787), but racist policies (Jim Crow era) made lawmakers resistant to granting equal rights to new, non-white populations.
  • “Most Americans did not want to include the black and brown inhabitants of those lands in the United States on terms of equality to white people.” [04:50]
• The Teller Amendment ensured Cuba’s independence after the war but allowed continued U.S. economic dominance; other acquired territories received no such provision.

4. The Insular Cases and ‘Unincorporated Territories’

[06:35-07:50]

• In Downes v. Bidwell (1901), the Supreme Court ruled Puerto Rico was not foreign internationally but was “foreign in a domestic sense”—not fully part of the U.S.
• This created the legal status of “unincorporated territories,” allowing Congress to govern these areas without granting them full constitutional rights.
  • “This new concept... allowed the US Government to legislate over the new lands without having to treat them like other parts of the Union, while also preventing the inclusion of their people into the US body politic.” [07:25]
• This facilitated tariff-free sugar flow to the U.S. while denying Puerto Ricans equal status.

5. The Struggle for Personhood and Citizenship

[08:00-09:40]

• The story of Isabel Gonzalez, who was denied entry into the U.S. as an "alien," led to the Gonzalez v. Williams (1904) Supreme Court case.
  • The Court invented the category of “non citizen nationals”: not aliens, not citizens, lacking full rights.
  • “They could travel to the American mainland without being considered immigrants, but they had no voting rights in the US.” [09:00]
• Full citizenship for Puerto Ricans arrived in 1917 with the Jones-Shafroth Act.

6. Modern-Day Puerto Rico: Ambiguous Rights and Representation

[09:45-11:00]

• Today, Puerto Rico is a self-governing Commonwealth with 3.2 million people.
• Puerto Ricans do not pay federal income taxes or vote in presidential elections.
• The Resident Commissioner in Congress has limited power (can debate, but not vote).
• Puerto Ricans pay Social Security taxes and receive federal benefits.

7. Bad Bunny’s Halftime Show as Political History

[11:10-13:00]

• Bad Bunny’s performance visualized Puerto Rico’s colonial past—depicting sugar cane workers (pillars of the colonial economy)—to contemporary struggles like last decade’s devastating power outages.
• He carried the historic pre-U.S. invasion Puerto Rican independence flag (banned from 1948–1957).
• Memorable closing:
  • “He ended up by shouting ‘God Bless America’ in English, echoing the United States mantra in an answer to right wing critics. And then he rejected the idea, animating the current US Administration’s deportation of black and brown people with the claim that they are not Americans and their culture will undermine American culture.” [12:45]
  • Bad Bunny then listed countries throughout the Americas—all seen as “America”—finishing with: “The football he carried said we are America.” [13:00]

Notable Quotes & Memorable Moments

• On U.S. racism and colonial status:
  “Most Americans did not want to include the black and brown inhabitants of those lands in the United States on terms of equality to white people.” [04:50]

• On the legal fiction of unincorporated territories:
  “It was foreign to the United States in a domestic sense because the island had not been incorporated into the United States.” [07:05]

• On Bad Bunny’s Super Bowl finale:
  “The football he carried said we are America.” [13:00]

Timestamps for Key Segments

• [00:05] - Bad Bunny’s Super Bowl Performance & Backlash
• [01:10] - Colonial Economic Motives: Sugar Trust & Territorial Expansion
• [04:05] - Racism & Statehood Policy Dilemmas
• [06:35] - The Insular Cases & Unincorporated Territories
• [08:00] - Isabel Gonzalez & the Invention of ‘Noncitizen Nationals’
• [09:45] - Modern Status of Puerto Rico
• [11:10] - Symbolism in Bad Bunny’s Halftime Show
• [12:45] - “We Are America” Conclusion

Tone and Style

The episode maintains Heather Cox Richardson’s characteristic blend of measured scholarly tone with accessible narrative, weaving together historical detail and present-day relevance. The storytelling anchors political critique in vivid anecdotes and Supreme Court cases, then circles back to contemporary cultural moments to show their historical resonance.

For those who missed the episode, this summary captures both the historical arc of Puerto Rico's ambiguous place within the U.S. and the powerful symbolism of Bad Bunny's halftime show as an act of cultural and political reclamation.