Ice Station Santa
During the first episode of the second season, a Maimtron 9000 is sent to the duo's office in an assassination attempt. They return the Maimtron to its sender, the North Pole, and find Santa shooting at anything attempting to come near him. Initially, an antagonist, Santa attacks them out of paranoia, noting the exorcism that is being held. Sam and Max aid in the exorcism, finding that the possessed Red Elf is harboring a monstrosity called the Shambling Corporate Presence and imprisoning it in Jello.
Santa, however, eats the Jello without knowing of its contents and is possessed by the monster. Unable to perform the exorcism again, the duo defeat and ship the possessed Santa to the creature's intended location: Satan in Hell. During the last episode of season two, What's Up, Beelzebub?, Sam and Max rescue Santa's soul, later discovering that the possession had occurred as a mistake in the Soda Poppers' plot to take over Hell.
Contrary to the popular image, this incarnation of Santa is short, quite grumpy, and ready to draw a gun to shoot just about anything without question. He also hates children, having chosen the Santa job so as to only have to deal with them once a year.
The Tomb of Sammun-MakIn the second episode of the third Telltale season, Sam and Max uncover the film reels portraying their ancestors Sameth and Maximus' exploits in uncovering the Devil's Toybox from the tomb of Sammun-Mak in 1901. Among the foes presenting a challenge, the businessman Nicholas St. Kringle (confirmed to be a younger version of the Santa seen in Ice Station Santa) seeks to possess the Devil's Toybox so as to get an edge on any latest toy development. He's rather cruel to his elves and quick to threaten when things do not go according to plan.
Following them through the tomb, Kringle attempts to shoot Sameth and Maximus and claim possession of the Toybox. Fortunately, Maximus is able to use Charlie Ho-Tep to fool Kringle into believing he killed them. On the train ride back home, Kringle steals the Devil's Toybox but has it stolen from him. After that, he isn't seen again until Sam and Max's encounter in the present day.