September 24, 2026

At just four years old, Theodore “Teddy” O’Malley already shares several interests with his famous namesake: animals, wildlife, the outdoors, and horses.

Recently, those interests came together in memorable fashion when Teddy dressed as President Theodore Roosevelt and won the costume class at the historic Warrenton Pony Show in Warrenton, Virginia.

Teddy’s fascination with President Theodore Roosevelt began after meeting a member of the Rough Riders Club at another horse show. He heard the story of Theodore Roosevelt’s remarkable 100-mile horseback ride from the White House to Warrenton and back in January 1909—a feat undertaken in difficult winter conditions to demonstrate the physical fitness standards he expected of military officers.

The story captured the imagination of the young horseman, who was born in Pittsburgh and is being raised in the Pennsylvania countryside.
Then Teddy discovered the famous image depicting Theodore Roosevelt riding a moose.

There was no turning back.

Teddy proudly entered the ring aboard Filigree—and the pair won the costume class.

Filigree is owned by family friend Katey Anfinson-Ralls, who has generously given Teddy the opportunity to ride her at horse shows as he develops his love of horsemanship.

Teddy’s connection to Theodore Roosevelt extends well beyond horses. He has a tremendous curiosity about animals, wildlife, science, and the natural world. At home, he currently cares for a pet salamander and tadpoles that he is watching transform into frogs. That curiosity has made President Theodore Roosevelt’s lifelong passion for natural history, conservation, wildlife, and outdoor life especially meaningful to him.

The timing of Teddy’s Roosevelt adventure is particularly special: he will celebrate his fifth birthday on September 27th!

“For the Theodore Roosevelt Association, stories like Teddy’s represent an important part of our mission to inspire the next generation of leaders,” said Chris Cosentino, Executive Director of the Theodore Roosevelt Association. “More than a century after his presidency, President Theodore Roosevelt continues to introduce young people to history, conservation, citizenship, courage, and the wonders of the natural world.”

We congratulate Teddy and Filigree on their victory—and wish this young Rough Rider a very happy fifth birthday!

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