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The Terrible Shotgun
Smiling Jack has a special shotgun called "The Terrible Shotgun". The Terrible Shotgun is the easily the most powerful of its kind in the game, dealing a whopping 80 base damage points with maxed out Small Arms skill. The main downside of the shotgun, like any other, is its high spread which forces the player to use the weapon in close quarters.
The easiest way to obtain the gun is by killing Smiling Jack, which, despite his friendliness, doesn't result in negative karma. However, there are other non-lethal ways to get this very powerful weapon, such as getting him to attack you and then shooting the shotgun out of his hand in V.A.T.S.
, and subsequently taking it when it's on the ground. He may be hostile the next time you see him, so be careful.