Next Monday is Columbus Day. Or should it be Indigenous People’s Day? According to the historian Matthew Restall we should be celebrating both Columbus and Indigenous People on Monday. The author of the timely The Nine Lives of Christopher Columbus, Restall places Genoa’s most famous sailor as a prisoner of history - endlessly protean to reflect each era’s changing values. The many lives of Columbus, then, is a mirror of how we have thought differently about him over the last 500 years. As history’s greatest saint and sinner, Christopher Columbus might be the ultimate Rorschach test. Tell me what you’ll be celebrating next Monday and I’ll tell you who you are. Happy hols!

1. Columbus Was a “Manic Narcissist” Who Believed He Was God’s Agent Restall discovered Columbus wasn’t likable—he descended into believing he was divinely chosen and could even be found in the Old Testament. This grandiosity was partly his undoing as a colonial administrator.

2. Columbus Failed as a Colonizer and Administrator Unlike the conquistadors who came after him, Columbus lacked political and diplomatic skills. He was “just a sailor”—son of a weaver, grandson of a cheesemaker—and Spanish authorities quickly sidelined him. He died in 1506, only 13 years after his first voyage, with a declining reputation.

3. The Columbus Day Debate Is About Different Columbuses Italian-Americans defend a 19th/20th century “Italian-American Columbus”—a symbol of immigrant achievement—while Indigenous Peoples’ Day supporters condemn the “historic Columbus” who began a colonization process that killed 70-90% of indigenous populations within a century. These groups are talking past each other about entirely different figures.

4. Conquistadors Were “Armed Entrepreneurs” Running Investment Companies Spanish conquistadors functioned like venture capital firms—assembling ships, soldiers, and supplies as investments, seeking returns through plunder and enslaved people, then winning authority positions to generate more profit while paying a 20% tax to the crown.

5. Columbus’s One Success: Founding a Noble Dynasty That Still Exists Despite his failures, Columbus achieved his main ambition—establishing an aristocratic dynasty. The title “Admiral of the Ocean Sea” granted in 1493 is still held today by the 20th admiral, a Spanish naval officer and businessman named Don Cristóbal Colón.

Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

BTB: Growing a Technical Consulting Firm (w/ Connor Jeffers, hapily)