The story of the Polo Bear begins not in 1991, when he first made a debut, but in 1902, when President Theodore Roosevelt went on a bear hunt in Mississippi. When Roosevelt declined to shoot a bear tied to a tree after a failed hunt, The Washington Post ran a cartoon of the event, inspiring toy sellers to name stuffed bears after him. Richard Steiff, one of the world’s most renowned toymakers, was amongst them.
As chance would have it, Jerry Lauren, Ralph Lauren’s brother, is a passionate collector of Steiff bears. In 1990, Jerry’s colleagues had a Steiff bear dressed in Jerry’s likeness—blue oxford shirt, tartan tie, cable-knit sweater—and presented it to him for his birthday. At the same time, a Western-inspired bear was given to Ralph.