Photo from the Key West Art and Historical Society
Per the Key West Art and Historical Society:
Robert the Doll is one-of-a-kind, handmade doll created around the turn of the 20th century. Standing 40 inches tall and stuffed with wood wool known as excelsior, he is dressed in a sailor suit and once bore painted features not unlike those of a jester. His unusual size indicates he may have been fashioned in the image of his constant companion – a boy named Robert Eugene Otto. The doll took Robert as his name, while the boy simply went by ‘Gene’. Together they would go on to make history.
Robert the Doll was given to Robert Eugene "Gene" Otto in 1904 by his grandfather as a birthday gift, reportedly manufactured by the Steiff Company of Germany. It's thought that the sailor uniform Robert the Doll wears was Gene's from childhood. Originally, the doll had a more expressive facial expression (eyebrows, rosy cheeks and red lips), though the paint has since worn off, leaving only a plain face with beady eyes. Per, again, the Key West Art and Historical Society:
Gene and Robert were ‘best friends’ growing up. Legend speculates voodoo played a part in Robert’s formative years, while interviews with those close to the Otto family indicate a great deal of emotional energy was placed upon the doll during Eugene’s lifetime. It is said that young Gene would shift blame when he misbehaved as a child, pointing to the doll and saying, “I didn’t do it. Robert did it”.
There are multiple stories of Robert giggling, playing tricks, and moving on his own. The doll would remain in Gene's possession until his death in 1974.
Today, Robert is kept on display by the Key West Art and Historical Society, and it's said that electrical equipment regularly malfunction and visitors often write letters asking for permission after being rude or taking a photo of Robert the Doll without asking, saying that they were haunted with misfortune until they apologized.