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HISTORY • CONVERSATION • CURIOSITY

20 Historical Figures
I’d Have a Drink With

Some I admire. Some fascinate me. A few simply have a lot of explaining to do.

THE PREMISE

One table. Twenty seats.

If I could sit down for a drink and a real conversation with twenty people from history, these are the people I would invite. The reasons are all over the map: leadership, politics, science, aviation, philosophy, art, war, faith, invention and plain old curiosity.

An important distinction

This is not a ranking of greatness, morality or admiration. It is a list of people I would want the chance to question, listen to, challenge or hear tell their own story.

The Twenty

01
Portrait of Abraham Lincoln

Abraham Lincoln

The Civil War, preserving the Union, leadership, politics and his famously dry sense of humor. I suspect this conversation could last all night.

02
Portrait of George Washington

George Washington

What did the first president really think about the country he helped create — and what would he make of the country it became?

03
Portrait of Adolf Hitler

Adolf Hitler

Not admiration. I would want to confront one of history’s most destructive figures and understand how he rationalized his ideology, decisions and crimes.

04
Portrait of John F. Kennedy

John F. Kennedy

The Cold War, Cuba, the space race, the presidency and the questions that still surround one of America’s most analyzed political eras.

05
Portrait of Ronald Reagan

Ronald Reagan

Hollywood, the presidency, the Cold War, the Soviet Union and the stories. Reagan seems like someone who could keep a table entertained for hours.

06
Portrait of Richard Nixon

Richard Nixon

Watergate would obviously come up, but so would China, Vietnam, foreign policy and the complicated personality behind a fascinating presidency.

07
Portrait of Franklin D. Roosevelt

Franklin D. Roosevelt

The Great Depression, the New Deal, World War II and what it was like leading the country through two enormous crises.

08
Portrait of Benjamin Franklin

Benjamin Franklin

Scientist, inventor, diplomat, writer, politician and professional troublemaker. This might be one of the livelier drinks on the list.

09
Portrait of Thomas Edison

Thomas Edison

Invention, entrepreneurship, competition, electricity and the difference between the Edison of the history books and the actual man.

10
Portrait of William Shakespeare

William Shakespeare

First question: how much did you actually write? After that, literature, theater and several centuries of people analyzing every damn word.

11
Portrait of Pope John Paul II

Pope John Paul II

Poland, communism, faith, world travel, the Cold War and his influence during one of the most consequential periods of the twentieth century.

12
Portrait of Ulysses S. Grant

Ulysses S. Grant

The Civil War, Lee, Reconstruction, the presidency and what history has gotten right — and wrong — about him. We may monitor the bar tab.

13
Portrait of Winston Churchill

Winston Churchill

World War II, Britain, Roosevelt, politics, leadership and enough wit to make this one of the more entertaining evenings on the list.

14
Portrait of Walt Disney

Walt Disney

Animation, creativity, risk, business, theme parks and one obvious question: what would Walt think of the company carrying his name today?

15
Portrait of Neil Armstrong

Neil Armstrong

Apollo 11 alone earns him a seat. I would want to hear what walking on another world actually felt like from the man who took the first step.

16
Portrait of Amelia Earhart

Amelia Earhart

Aviation, exploration, breaking barriers and — yes — eventually I would have to ask exactly what happened on that final flight.

17
Portrait of Aristotle

Aristotle

Philosophy, ethics, government, science, education and human behavior. It would be fascinating to introduce an ancient thinker to the modern world.

18
Portrait of Albert Einstein

Albert Einstein

Relativity would only be the beginning: science, nuclear weapons, war, politics, religion and how one of history’s great minds viewed humanity.

19
Portrait of Marie Curie

Marie Curie

A pioneering scientist, two Nobel Prizes, radioactivity, perseverance and succeeding in a scientific world hardly designed to welcome women.

20
Portrait of Leonardo da Vinci

Leonardo da Vinci

Artist, engineer, inventor and anatomist — a mind that seemed centuries ahead of everyone else. There might not be enough hours in the evening.

Portrait test: images are loaded from Wikimedia Commons. The selected images are public-domain/free-use files; the Pope John Paul II portrait is by Beyond Forgetting and licensed CC BY 2.0. Click any portrait to open its Commons file page. This credit block can be refined or moved if we keep the photo design.
FIRST ALTERNATE

Mark Twain

Probably the funniest evening on the list. If anybody above cancels, Twain gets the chair immediately.

Proud American.

Freedom isn't free.
Honor. Remember. Never Forget.

Flag of the United States United States POW/MIA flag

All Gave Some.
Some Gave All.

You are not forgotten.

★ Honoring those who served. Always. ★