“Absolutely outstanding!” Randolph Churchill, great-grandson of Sir Winston Churchill
Winston Churchill and Theodore Roosevelt sat down to dinner. History, politics, empire, and ego were on the menu.
A dramatic work of historical fiction tells the story of their first and last meeting.
“I saw the Englishman, Winston Churchill here. He is not an attractive fellow.” Theodore Roosevelt, July 12, 1901
Not An Attractive Fellow
Not An Attractive Fellow imagines the historic meeting between Winston Churchill and Theodore Roosevelt in a dramatization, based on the original screenplay written by Lawrence Siskind. The production offers a lively theatrical look at two outsized personalities at the beginning of a new century—and at a young Churchill still decades away from becoming the statesman the world would come to know.
The full play runs 120 minutes. A condensed version runs 70 minutes.
Cast:
Theodore Roosevelt. 42 years old. New York Governor and Vice President elect.
Winston Churchill. 26 years old. English journalist and newly elected Member of Parliament.
Elijah Marshall. The Governor’s butler, who served with Roosevelt in Cuba. He mediates the intensifying conflicts between the two famous diners.
Alice Roosevelt. The Governor’s daughter by his deceased first wife. Sixteen going on 17, she arrives late and flirts shamelessly with the English visitor.
The Plot
In December 1900, Theodore Roosevelt invited a young Winston Churchill to dinner at the Governor’s Mansion in Albany. Roosevelt, then 42, had just been elected Vice President and was preparing to move to Washington. He was one of America’s most celebrated political figures. Churchill, just 26, was an ambitious newly elected Member of Parliament, touring the United States as a lecturer.
The two men dined alone. We do not know what was said that night. But we know what happened afterward. Churchill left the dinner thinking he had made a positive impression on the older man. Roosevelt thought differently.
Over the ensuing years Roosevelt described Churchill as conceited, vulgar, cheap, and thoroughly unlikeable. He avoided opportunities to meet him again.
What happened?
Engineered Precision, Delivered
The traditional explanation is that the two men were too much alike. This play imagines other possibilities.
Drawing on their letters, biographies, politics, personalities, and experiences, it reconstructs the only dinner Theodore Roosevelt and Winston Churchill ever shared: an encounter between two extraordinarily confident men, one expecting the deference due an elder statesman and the other determined to meet him as an equal.
Both would go on to shape the twentieth century. But first, they had to survive dinner.
Performed at the Union League in Philadelphia, at the International Churchill Society Annual Conference.
October 16, 2026.
Directed by Rosemary Hay
Produced by Rob Shwab and Lawrence Siskind
https://winstonchurchill.org/2026-international-churchill-conference/
References
When Teddy Roosevelt Had Winston Churchill to Dinner, Finest Hour (January 25, 2022), https://winstonchurchill.org/publications/finest-hour-extras/teddy-roosevelt-has-churchill-to-dinner/
Winston Churchill: The Last Lion and One of the First Proponents of Trademark Coexistence Agreements, ABA Landslide Magazine (March 1, 2020), https://law-journals-books.vlex.com/vid/winston-churchill-the-last-907235688
Assessing Teddy Roosevelt, To Put It Bluntly (July 6, 2020), https://toputitbluntly.com/2020/07/06/assessing-teddy-roosevelt/
Winston Churchill’s Life Mattered, To Put It Bluntly (June 15, 2020), https://toputitbluntly.com/2020/06/15/winston-churchills-life-mattered/