Hester is unique amongst the Teddy Scares, because he has no memory before waking up in the dump. There are clues to his origins. The bag he woke up in had other stuff in it, which may or may not hold the secret to his past. Later, a toy collector’s magazine turned up in the dump. It contained an article on Hester’s brand of bear, which is from the 1880s. He has all the evidence laid out in his home and many nights he goes through the material like a detective trying to solve a great mystery.

Hester is an eloquent bear, who loves to hear himself speak. A bookworm, his empty head is brimming with a vast vocabulary. A sharp mind and tongue are other traits of his. He can build you up or tear you down with a clever word or two. His dark sense of humor is unparalleled amongst the other bears. Though he certainly enjoys his own company, Hester likes to spend time with Edwin. They are the smartest bears in the dump and share a love of books and history. He also has his roaches, which reside in him. For an unknown reason, he has managed to make some kind of telepathic connection to them. They are his eyes and they will obey his commands.

The other bears don’t care much for Hester, but they do have a degree of respect for him. They will often go to the eyeless bear, when a problem requires brains instead of brawn. If the bears have any leaders, he would be one of them.

Hester has a secret, which he keeps from the others. Being over 100 years old his body is a rotted mess. The constant in and out of his roaches have eroded much of his stuffing too. Privately, he has begun to notice some early signs of memory loss, possibly from the loss of stuffing. Because of this he has devoted his free time to discovering why the bears are alive in the hopes it can offer answers to his situation.