Welcome back to A Little Wiser. Keep an eye out as you read today, we’re introducing a brand-new feature and sharing a fantastic newsletter recommendation. Benjamin Franklin famously remarked that an investment in knowledge yields the highest returns. Here’s your latest dividend! Today’s wisdom explores:

  • The True Story of the Silk Road

  • Leo Tolstoy’s Struggle to Live His Truth

  • The Surreal Saga of Dennis Rodman in North Korea

Grab your coffee and let’s dive in.

HISTORY
🐪 The True Story of the Silk Road

In 138 BCE, Emperor Wu of Han sent a diplomat named Zhang Qian westward into Central Asia on a military mission to forge alliances against the empire's enemies. The resulting connections gradually became the arteries of the most consequential trading network in human history. The name "Silk Road" was coined by a German geographer named Ferdinand von Richthofen in 1877, nearly two thousand years after the routes opened, and it was always something of a misnomer. Few merchants ever traveled the full 4,000-mile length; goods instead passed through chains of middlemen across dozens of hands between China and Rome. Silk was actually only one of hundreds of commodities moving in both directions.

The routes attracted, shaped, and were transformed by some of history's most consequential figures. Alexander the Great's campaigns in the 4th century BCE pushed Greek influence deep into Central Asia, laying the cultural groundwork that made later east-west exchange possible. Centuries later, the routes reached their golden age under the Mongols. Genghis Khan's successors created a unified political order stretching from the Pacific to Central Europe. Known to historians as the Pax Mongolica, it allowed merchants to travel thousands of miles with a reasonable expectation of safety. It was under Kublai Khan's sponsorship that a 17-year-old Venetian merchant named Marco Polo set out in 1271 and spent the next two decades traveling across Asia. When Polo was imprisoned in Genoa years later, he dictated his experiences to a fellow prisoner, producing the book that introduced an entire generation of Europeans to the wealth of the east. On his deathbed he reportedly said he had not written half of what he saw, knowing he would not be believed.

The people who actually made the Silk Road function across its long history were largely invisible to the civilizations at either end. The Sogdians, an Iranian trading people based in the oasis cities of Central Asia, operated as the human nervous system of the entire network for centuries. They established merchant colonies from China to the Mediterranean and served as brokers, translators, and bankers along the full length of the route. After the Ottoman conquest of Constantinople in 1453 and the increasing difficulty and expense of overland trade, European merchants desperate to reach Asian markets launched the sea voyages that became the Age of Discovery. The Silk Road's decline indirectly produced Columbus, Vasco da Gama, and the beginning of the modern world.

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LITERATURE
📖 Leo Tolstoy’s Struggle to Live His Truth

By any measurable standard, Tolstoy had achieved everything a writer could hope for before he turned fifty. War and Peace, completed in 1869 after six years of relentless revision, contained 580 characters and over 560,000 words. It is widely regarded as one of the greatest novels ever written. His wife Sophia copied it out by hand multiple times as he rewrote entire sections, and she played a major role in helping prepare it for publication. Anna Karenina followed, and its opening line, "All happy families resemble each other; each unhappy family is unhappy in its own way," became one of the most famous sentences in literary history. Shortly after completing Anna Karenina, Tolstoy fell into a profound existential crisis, describing in his memoir A Confession a paralyzing terror of death that made his extraordinary success feel completely hollow.

What followed was one of the most radical transformations in literary history. Tolstoy emerged from his crisis with a new set of beliefs built around a stripped-down reading of the Sermon on the Mount: rejection of wealth, refusal to cooperate with state authority, and manual labor as a spiritual practice. He attempted to renounce the copyrights to many of his earlier works, gave away large portions of his fortune, and began dressing and working like a peasant on his own estate. His wife Sophia, responsible for managing the family's finances and their thirteen children's futures, was devastated and fought him bitterly over the inheritance for years. Their marriage, which had once been the support structure that made his greatest writing possible, deteriorated into what biographer A.N. Wilson called one of the unhappiest in literary history. His philosophy of nonviolent resistance deeply influenced a young Mahatma Gandhi, who began corresponding with the aging Tolstoy in 1909 and named a communal farm in South Africa after him.

The end came with a final act of extraordinary stubbornness. On October 28, 1910, at the age of 82, Tolstoy gathered a few belongings in the middle of the night and secretly fled his family estate at Yasnaya Polyana, unable to reconcile the life of privilege he was still living with the beliefs he had spent thirty years preaching. He boarded a train with no clear destination, fell gravely ill within days, and died ten days later at a remote railway station called Astapovo, surrounded by journalists and crowds who had followed the news of his flight across Russia. He was buried in a simple grave with no headstone at Yasnaya Polyana, exactly as he had requested. The man who wrote two of the most enduring novels in human history spent the last chapter of his own story trying to become someone entirely different, and never quite managing it.

A full-color photo of Leo Tolstoy taken on May 23, 1908 at his residence at Yasnaya Polyana.

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CULTURE
🏀 The Surreal Saga of Dennis Rodman in North Korea

Kim Jong Un reportedly grew up watching the Chicago Bulls during Michael Jordan's championship dynasty in the 1990s, developing a passion for basketball that became one of the few known windows into his private life. When he took power following his father's death in 2011, North Korean officials quietly reached out through Vice Media to arrange a visit, hoping to leverage that shared obsession into a rare cultural exchange. The person they wanted most was Michael Jordan, who declined. Scottie Pippen also passed. The invitation eventually landed with Dennis Rodman, the Bulls' famously eccentric rebounder, who accepted without hesitation and arrived in Pyongyang in February 2013. Rodman later said that when he stepped off the plane, he genuinely thought he was going to prison. Instead, he found a literal red carpet, a throne-like chair, and a crowd treating Kim Jong Un like a deity.

The two struck up a rapport that Rodman described publicly as a friendship for life. Kim gave Rodman the full treatment, putting him up in the finest hotel, surrounding him with staff, and, given Rodman's well-known appetite for a good time, making sure the evenings lived up to expectations. Rodman later recalled that the parties were something else entirely, describing tables lined with around fifty bottles of vodka as the two of them played drinking games together deep into the night. Rodman visited North Korea five times between 2013 and 2017, making him one of the very few Westerners to spend sustained personal time with Kim during that period. On a trip,in 2014 Rodman stood on a basketball court in Pyongyang and sang Happy Birthday to Kim just days after Kim had his own uncle executed. When an American missionary named Kenneth Bae was being held in North Korea, Rodman wrote Kim a letter addressing him as "my dear friend for life" and asking for Bae's release. Bae was eventually released later that year and credited the attention Rodman's visit had generated as a catalyst for his release.

The deeper oddity of the whole arrangement is what it reveals about how personal relationships function at the level of geopolitics. Before Mike Pompeo's secret visit to Pyongyang in 2018 to lay the groundwork for the Trump-Kim summit, Rodman was among the most connected Americans to the North Korean leadership, a status he had acquired through no institutional backing, no diplomatic training, and no government authorization whatsoever. Whether that channel ever amounted to anything substantive remains unclear. What is clear is that the most isolated and militarized state on Earth spent several years maintaining its warmest relationship with the United States through a retired basketball player with dyed hair who once married himself.

North Korean leader Kim Jong-Un and former NBA star Dennis Rodman speak at a basketball game in Pyongyang on Feb. 28, 2013.

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Until next time... A Little Wiser Team

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