Five Funny Stories About Young Theodore Roosevelt

Theodore Roosevelt had an infectious personality and told lots of funny stories.  He also was the subject of reminiscences by family and friends.

1. His father, the first Theodore Roosevelt, was concerned about the health of his children and wanted them to get as much fresh air as possible.  So at the back of their brownstone in New York City, he removed a wall from a second story bedroom to make an open porch. The two boys and two girls went out on pleasant days to exercise. According to older sister Anna, one day a neighbor happened to look up to see nine-year-old “Teedie,” as he was called, on the end of a seesaw.  He, on the far seat, and his cousin, on the seat closest the house, were balancing it on the railing two stories up! The neighbor rushed in to tell his mother, Martha, who went out and firmly pulled the boys in. She said, “If the Lord wanted Theodore, He’d have taken him long before now.”

 “Teedie.”  National Park Service photo.

2. During the family’s second trip abroad when Theodore was fourteen, the three younger children stayed with a German family to learn the country’s culture.  He caught the mumps, though, and his asthma flared up.  His mother came to take them to Switzerland for the mountain air.  They packed, and Theodore told Martha he was ready to go, so she checked his trunk.  It seemed unusually heavy.  He’d removed quite a few articles of clothing and replaced them with large rocks he wanted to study.  The clothes went back in, but he managed to take some smaller rocks along in his pockets.

3. Fred Osborn was a good friend who shared an interest in nature and often invited Theodore to his home near Garrison, New York.  Fred’s brother Henry told of the time the boys were on a walk and doffed their hats as they met the carriage of Hon. Hamilton Fish, the current United States Secretary of State, and his wife.  A frog jumped from Theodore’s head to the ground, having been stored under the hat because his pockets were full.

4. Theodore hunted birds and game in the Adirondack Mountains.  At fifteen he was guided around St. Regis Lake by a man named Mose Sawyer.  To show appreciation after the trip, Theodore gave him two stuffed birds preserved with arsenic.  Unfortunately, the birds, and Mose’s cat which ate them, did not last long.


Theodore at sixteen.  Harvard University photo.

5. He was shy in his teens though he attended social events such as dancing parties. At the family’s summer home in Oyster Bay, Long Island, Theodore liked to take girls out for rowboat rides. His sister Corinne wrote about an early morning when he rowed to a dock close to a girl’s house.  As it was several hours before he said he’d be there and no one was around, he undressed to go for a swim.  Then he crawled under the dock and took a nap.  He woke up to the sound of two girls talking on the boards above his head.  Too late he realized the boat had drifted away with his clothes in it, and had to wait until they left before he could finally swim to the boat and his clothes, and return home.

All right, I have one more, but it is not about the young Theodore.

When he was grown, he and two guides took a hunting trip in Idaho. He had a camera with him and wanted to photograph a particularly beautiful waterfall. To get closer, he asked the men to lower him over a cliff with one end of a long rope tied around his waist and the other end anchored to a tree. He took the picture and signaled for them to pull him back up. They pulled. And they pulled. And they pulled.  None of their efforts could raise him. He was dangling so far above the river that it would have been dangerous to cut the rope, and finally they decided the only thing to do was double a shorter rope and tie it to the first to get him closer to the water. One of the men ran down to the shore where Theodore tossed the camera to him; the other cut the rope. He fell into the river, bruised but otherwise all right. Does this remind you of the little boy in the first story? One of TR’s friends said, “You must always remember he is about six.”

President Roosevelt at Yosemite, several years after the incident in Idaho.  Harvard University photo.

Sources: Lillian Rixey, Bamie, Theodore Roosevelt’s Remarkable Sister; Frank Russell, Theodore Roosevelt Typical American; Henry Fairfield Osborn, Impressions of Great Naturalists; Paul Russell Cutright, Theodore Roosevelt the Naturalist and Theodore Roosevelt the Making of a Conservationist; and Corinne Roosevelt Robinson, My Brother Theodore Roosevelt.

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