| “ | The snow will turn red with the blood of the naughty! | „ |
| ~ Santa Claus |
In the Sam & Max Telltale video game series, Santa Claus himself appears as an antagonist during different times. In the present, he is an aggressive victim of a demonic possession while in the past, a greedy businessman pursuing the duo's ancestors Sameth and Maximus for possession of the Devil's Toybox.
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. While Sam and Max initially believe Santa to be attacking them due to demonic possession, and conduct an exorcism to alleviate it. However, his hostility is revealed to actually be (at least partially) out of paranoia, and the real victim of demonic possession was one of his elves, who was possessed by a being known as the Shambling Corporate Presence. With the help of the Ghosts of Christmas Past, Present, and Future, Sam and Max are able to safely contain the beast inside a plate of Jello.
Santa, however, eats the Jello without knowing of its contents and is possessed by the Corporate Presence. 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 New, 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 (though the elf's death was on purpose).
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-Mak
In 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.