In the mid-1930s, as John F. Kennedy and Kirk LeMoyne “Lem” Billings transitioned from prep school to college, their already strong friendship from Choate deepened into one of the most enduring bonds in American political history.

What began as teenage camaraderie at the elite Connecticut boarding school evolved into a supportive partnership filled with laughter, loyalty, and shared adventures that shaped both men profoundly during their university years.

The Man Who Was JFK’s Best Friend / Via internet

Following their 1935 graduation—after Lem repeated his senior year to stay with Jack—the pair briefly attended Princeton University together that fall.

Rooming with Choate friend Ralph Horton Jr., they embraced campus life, exchanging jokes and creating memories captured in a festive Christmas greeting that showed their tight-knit trio enjoying the Ivy League atmosphere.

The Man Who Was JFK’s Best Friend / Via internet

However, JFK’s chronic health issues, including severe stomach problems and jaundice, forced him to withdraw from Princeton after just weeks.

He recovered and transferred to Harvard University in 1936, while Billings continued his studies at Princeton, majoring in art and architecture and writing his senior thesis on Tintoretto.

The Man Who Was JFK’s Best Friend / Via internet

Despite the geographic separation between Cambridge and Princeton, their connection remained unbreakable.

They exchanged frequent letters brimming with humor and personal updates, and Lem often visited Jack at Harvard or joined the Kennedy family at Hyannis Port and Palm Beach during holidays, proving distance could not weaken their bond.

The Man Who Was JFK’s Best Friend

A pinnacle of their college friendship unfolded in the summer of 1937 with an epic European road trip. Just before JFK’s junior year, the duo sailed aboard the S.S. Washington, then toured France, Italy, Germany, and the Netherlands in a Ford convertible, documenting every moment in diaries and candid photos.

Traveling together through pre-war Europe, they immersed themselves in culture while navigating challenges with youthful energy.

They even adopted a dachshund puppy named Dunker in Germany as a travel companion, though allergies later required rehoming the dog in The Hague—an anecdote that underscored their spontaneous, carefree spirit.

Best Friend | Princeton Alumni Weekly / Via paw.princeton.edu

The journey broadened their horizons and solidified mutual trust, as the friends relied on each other amid unfamiliar landscapes and rising global tensions.

Back on campus, Lem thrived academically while JFK dove into government studies and extracurriculars at Harvard, frequently seeking each other’s advice and encouragement.

Their dynamic was defined by playful teasing and unwavering loyalty.

Lem’s quick wit kept Jack laughing through illnesses and pressures, while JFK accepted Lem completely, including his sexuality—a rare openness in that era that fostered profound acceptance.

Via Internet

By integrating into Kennedy family vacations and gatherings, Lem became more than a friend; he was treated like an additional brother, sharing holidays and offering constant support during Jack’s health struggles.

This close relationship cultivated during their college days proved foundational for the decades ahead. Lem remained JFK’s most trusted confidant through military service, political campaigns, and the White House, serving as usher at his wedding and frequent houseguest until Kennedy’s assassination in 1963.

Their college-era bond exemplified how youthful friendship can endure as a lifelong anchor.

Leave a Reply

Your email address will not be published. Required fields are marked *