Endorsed by Churchill's Great-Grandson

“I have heard many people attempt to play the role of my great-grandfather, but without hesitation, Randy Otto takes the role to a whole new level. Randy does not attempt to be Winston Churchill, Randy IS Winston Churchill.” – International Public Speaker & Author, Jonathan Sandys

Churchill's Leadership Today

Audiences learn why Winston is still the all-time standard of leadership, as relevant today  – at the age of 143 – as he was in life.

Ask Winston

In every performance, audience members have the opportunity to ask Winston a question.

2020 Tour Schedule

Randy’s timeless performances are always tailored to your specific audience, and include ‘Ask Winston‘, an unforgettable, interactive Q&A with Winston himself!

Jan 10-14 APAP New York, NY Private Event
Jan 16 Iowa State Association of Counties West Des Moines, IA Private Event
Jan 27-31 Acansa Arts Festival Little Rock, AR Ron Robinson Theatre
Feb 28 – Mar 1 National Speaker Association Winter Conference Houston, TX Professional Development
Mar 2-3 North Coast Repertory Theatre Solana Beach, CA Buy Tickets
Mar 5 Capitol Center for the Arts Concord, NH Buy Tickets
Mar 7 Sipe Center Bridgewater, VA Buy Tickets
Mar 11 Christensen Performing Arts Hall at BIG ARTS Sanibel Island, FL SOLD OUT
Mar 14 Schorr Family Firehouse Stage Johnson City, NY Buy Tickets
Mar 25-27 “Think Big, Smart Small” – Saint Clement’s Church Conference 2020 London, England More Info
May 6 PMI-NEW Professional Development Days Workshop Lambeau Field, Green Bay, WI More Info
May 8-11 Normandy Strategic Leadership Seminar Normandy, France More Info
May 16 British Gala Festival Kansas City, MO More Info
Jun 12 Vistage Retreat Appleton, WI Private Event
Aug 7 Winston at the Edinburgh Festival Fringe Edinburgh, Scotland More Info
Sep 1-3 Western Arts Alliance San Diego, CA Professional Development
Sep 9 Arts Midwest Omaha, NE Professional Development
Sep 17-18 PHCC 125th Year Annual Conference Green Bay, WI Private Event


arts midwest national speakers association wisconsin counties association TEC executive committee san angelo pac oconomowoc arts center lawrence universityhillsdale college first trust churchill collegevistagethe churchill society

Randy Otto 

With over four decades of committed academic Churchill study, Randy Otto is a walking encyclopedia; an expert on virtually all aspects of Churchill’s life. “What impresses me about Randy is not just his portrayal of Churchill, but his mastery of the historical sources underpinning his characterisation, and his enthusiasm for its importance.” Allen Packwood – Director, Churchill Archives Centre – Churchill College, Cambridge University, Cambridge UK

Astonishingly believable as Winston himself, Randy’s personalized CHURCHILL LEADERSHIP KEYNOTE speeches are delivered confidently “in character.” Otto’s acclaimed portrayal of Winston Churchill concentrates on the man himself, causing President Harry Truman’s Nephew, John Ross Truman to state: “…an evening spent with Randy Otto is as close as you will come to an evening with the colossus of the age: Winston Churchill.”

“Randy Otto steps onstage and you simply take for granted that Winston Churchill himself is up there talking to you.” Winston Churchill’s Great-Grandson, Jonathan Sandys

Churchill Leadership Keynote Choices

All Churchill leadership keynotes are always tailored to your specific audience and includes Ask Winston, an interactive Q&A with Winston himself!

Painting as a Pastime: Banishing the Black Dog

In Otto’s “Pastime”, commissioned by the National Churchill Museum, and honoring Winston Churchill’s book of the same name, the audience is transported back to one of the darkest periods in Churchill’s life, the early days of WWI and the fallout from the failed...

Winston Churchill: CEO

Churchill’s 8 Timeless Leadership Principles for 21st Century Leaders. Invaluable insights directly from the leader CEO’s (and audiences everywhere!) admire most. Delivered with Churchill’s distinctive wit and style.

Winston Churchill: The Blitz

Autumn. 1940. London. Never have so many been so inspired by one man heroically leading the British people to Victory from a London Rooftop. Your audience lives through one night of The Blitz, the German bombing of London. But never fear. Winston is here!

Winston Churchill: Man of the Century

From birth to death and beyond…a biographic masterpiece. Journey with Winston from his 18th Century upbringing, through careers as soldier, journalist, politician, statesman then ultimately exploring Churchill’s lasting legacy of leadership and its meaning to us in the 21st Century.