Shaggy Bears are antagonistic creatures that made their first appearance in Mask of Bimshire and the Offset comic book. Ragged Spectres that haunt the night, they are often accompanied by flute music and are known to haunt customers who owe outstanding debts to the obeah trade, Dark Arcs.
Midnight Tukband
Shaggy Bears are controlled by a member of the Midnight Tukband, Isaac. His music controls them like minions to do his bidding. Little is known about Isaac, except he that he uses a strange flute that he plays expertly. In Mask of Bimshire, during an encounter with Linseed Beckles, he remakes that it would take 1000 Shaggy Bears to kill him, hinting that he can control vast numbers of Shaggy Bears at once should the need arise.

Design
Shaggy Bears come in many different looks, but they have consistent features. They don spikey wooden masks that hide their faces, with glowing eyes which go from yellow to violet. In the comic, the top spikes of the mask act as antennae which attract the flute music that summons them. When active, this causes their eyes to change colour. They also have rags that cover their body given them a spectral appearance. They sometimes have simple tattered shoes or go barefoot. Their frames are often lithe, wiry, slender and sometimes short that lends to their agile movement.

Personality
Shaggy Bears act as lifeless puppets that are only active when flute music plays. They don’t show any emotion or react to pain, however they tend to react violently when faced with aggression, as an automatic failsafe.
Weapons/ Fighting Abilities
Shaggy Bears are acrobatic, agile fighters that are extremely hard to attack even from seasoned fighters like Kyle or Collins. Their movements are dance-like, coordinated with the intricate flute music that herald their arrival. Their fighting style has been akin to Capoeira with flairs and kicks. However, they can be seen to be teleport in and away from battlefields at a moment's notice as well. In Mask of Bimshire, it took both Kyle and Collins working together to even harm one of them. Proving that Shaggy Bears are daunting opponents.
Cultural References and Allusions
Shaggy Bears are a part of Caribbean Folklore, particularly in Barbados as they are part of the cultural celebrations associated with the Crop Over Festival. They are also accompanied by tuk-band music. Delvin Howell came up with the idea when witnessing them during a festival and envisioned a more haunting and terrifying version of them for the story.
He also admitted to being influenced by the Heartless from Kingdom Hearts and the Skull Kid from Legend of Zelda, when coming up with the design for the Shaggy Bears in Offset.
Shaggy Bears are also called S-Bears which is a play upon the word “esper” which is a person with paranormal abilities.