Ice Assassin here has probably never heard a Christmas song in his life and has absolutely no idea what Crowley is talking about. The winter theme only goes so far.

"What makes you think that?" Because actually, he is. Just because the two Grandmasters dress like they're from the 16th century doesn't mean the rest of the world doesn't have all kinds of cool tech that he absolutely refuses to use. Could he have sent a drone into locations to scout around for him? Sure. But instead he has an old timey telescope that works equally as well in his mind.

"And I presume your friend would be insulted by this as a gift?" Okay now he's understanding a little bit better.