teddy bear gang 

a hella dangerous gang started in florida, not to be fucked with.

damn homes you should stay inside, the teddy bear gang is outside rn

teddy bear gang by Altszio February 28, 2019

teddybear gangsta 

A person identified as a gangsta (usually as per hip-hop culture and/or actual gang affiliation) who, despite their thuggish demeanor, appear cute and cuddly. This definition has no bearing over the actual content of any lyrics, which is usually anything but cute.

Ice Cube is such a teddybear gangsta; waving a gun and shit but all you want to do is give him a big hug.

teddybear gangsta by KRE13 March 28, 2010