Why We Sleep With Teddy Bears: The Surprisingly Political Origin of America’s Most Beloved Toy

I knew the teddy bear was named after Theodore Roosevelt but I assumed it was some vague association, like maybe he liked bears. I did not know it came from a specific hunting trip, a specific cartoon, a specific political moment, and a specific Brooklyn candy store owner who sewed a stuffed bear and put it in his window with a handwritten sign. All of that happened, in sequence, in 1902. The toy that resulted is now one of the most produced objects in human history.

The Hunt That Started Everything

In November 1902, President Theodore Roosevelt traveled to Mississippi at the invitation of Governor Andrew Longino for a bear hunting trip. After three days in the field, other members of the party had located bears. Roosevelt had not. The president’s hunt was shaping up to be an embarrassing failure.

His guide, a man named Holt Collier, solved the problem. Collier tracked down an old, exhausted black bear, ran it with dogs for hours, and tied it to a willow tree. Here was a bear for the president to shoot.

Roosevelt looked at the bear and refused. He declared it unsportsmanlike to shoot an animal in that condition. He instructed his aides to put the bear down out of mercy, but he would not pull the trigger himself on a tethered, beaten animal. This distinction, between mercy and trophy, apparently mattered a great deal to Roosevelt. He had helped found the Boone and Crockett Club in 1888 around exactly this kind of fair chase ethic. Word spread quickly. By November 16, 1902, it had reached the Washington Post.

The Cartoon and What It Was Actually About

Clifford Berryman was the Washington Post‘s chief political cartoonist. He drew a sketch of the Mississippi incident showing Roosevelt in his Rough Rider uniform, his back turned to a small, cowering bear. He titled the cartoon “Drawing the Line in Mississippi.”

That title carried a double meaning. One reading referred to Roosevelt’s hunting code, the line he refused to cross. The other referred to Roosevelt’s recently stated position on racial violence in the South. Lynchings of Black Americans were occurring with grim regularity and minimal legal consequence. Roosevelt had been making public statements against racial violence, and “drawing the line in Mississippi” carried obvious resonance in that context.

This second meaning has largely been forgotten in the popular retelling of the teddy bear origin story. Most people now know the bear part. The political commentary that gave the cartoon its title is not part of how the toy gets explained to children. The cartoon spread rapidly. Newspaper reprints across the country gave the image national circulation within days.

The Brooklyn Candy Store

Morris Michtom ran a candy and novelty shop in Brooklyn with his wife Rose. He saw Berryman’s cartoon and had an idea. Rose sewed two small stuffed toy bears. Morris put them in the shop window with a hand-lettered sign: “Teddy’s Bear.”

The bears sold immediately. Morris then wrote to President Roosevelt asking permission to use his name commercially. Roosevelt apparently granted permission, though the original letter has never been found. Within a year, the Michtoms had founded the Ideal Novelty and Toy Company. It became one of the first major American toy manufacturers, built on a product that had not existed twelve months earlier.

Simultaneously and independently, in Germany, Margarete Steiff and her nephew Richard were producing a plush toy bear that reached American retail in 1903. Some sources suggest Richard Steiff had designed the bear before the Roosevelt hunting incident, and that the name “teddy bear” caught on because of serendipitous timing. Whether the toy or the name came first is a minor historical dispute. What is not disputed is that within a year of the Mississippi trip, teddy bears were being manufactured and sold on two continents.

Why Berryman’s Bear Got Smaller

The original Berryman cartoon showed a full-grown bear about the same size as Roosevelt’s guide. Within weeks, however, Berryman started redrawing the bear as smaller, rounder, and more obviously cute. He used the bear as a recurring symbol throughout Roosevelt’s presidency, inserting a small cuddly figure into cartoons as a Roosevelt stand-in or companion.

This redesign is part of why the teddy bear became a children’s toy rather than a novelty item. The original was an adult animal in distress. The Berryman bear, by contrast, evolved into something that looked designed for a nursery. A political cartoonist kept drawing it cuter with each iteration until the image had become something entirely different from what it started as.