jackboy

plural jackboys

1. A street thug who is part of a gang of thieves.

   We ducked and dodged law, and jackboys, only to hand our hard earned cash over to another hustler; a hustler greater than us.

   2011, Hector Stone, Trapstarz, page 29

   2 more examples

   Ordell asked one of his jackboys to get him a car with keys in it and leave it in the Ocean Mall parking lot over by the beach. The jackboy asked him what kind of car he wanted. Ordell said, 'One has a big trunk with a shotgun in it.' He liked jackboys because they were crazy. They made their living ripping off street dealers for their blow and change and busting into crack houses with assault weapons.

   2012, Elmore Leonard, Rum Punch

   "Get you stupid ass over there by the chip display and don't move," the robber instructed as he positioned himself to where he could see both David and Nicole with minimal movement. That act alone let David know the guy in the Oakland Raiders pullover was an experienced jackboy.

   2014, Antonio David Hart, Chess Game of the Gods