The Magician Tarot card represents, obviously, the magician, the one who does magic. The magician stands in their vestment, their instruments in hand or at hand: the Wand, Cup, Sword, Pentacle, and Staff. The wand pointing up and finger pointing down suggest that the Magician mediates something between the supernal and infernal, celestial and terrestrial, spiritual and material — and perhaps artificial and natural. This is the actualized or realized Magician; it took work (or Work-with-a-capital-W, the Great Work, Magnum Opus) to get here, to become this.
I see chaos magic as something of an attempt to get back to the card that immediately precedes the Magician: the Fool. Recall my earlier association of the chaos in chaos magic with the Prima Materia of alchemy. The Fool represents creative, childlike energy, open mindedness, and the beginning of things, including going back to the beginning or perhaps “back to basics” or first principles. Compare the Beginner’s Mind of Zen Buddhism. The Fool is ruled by Uranus, the planet of innovation and revolution, which according to some is a higher octave of Mercury, the planet associated with the Magician. You may find many correspondences to the Fool in chaos magic: the Discordian character of some of the rituals and personae; banishing with laughter; the tendency to deconstruct magic and ritual; and Carrol’s Ouranos Rite; to name just a few examples. The “trickster” aspect of many magicians also suggests the Fool — think of the jester, and one of the variants of the magician, the juggler or bateleur, synonymous with bouffon, “buffoon.” There is also the connection between chaos magic as idiosyncrasy or eccentric magic (not merely eclectic magic), and the word idiot (both derived ultimately from the Greek ἴδιος, “private”).
The Fool reversed indicates the negative aspects of folly, including chasing novelty, whimsy, and adventure so much that one never develops the discipline or depth to become the Magician. The Fool is so focused on the heavens they are about to step off the edge of a cliff — a very different relationship between the above and below than we see depicted in the Magician. This is the side of chaos magic that is often criticized by other magicians and sometimes even chaos magicians themselves. I think good chaos magic finds a balance or useful oscillation between the carefree energy of the Fool and the discipline of the Magician, not allowing the former to degenerate into carelessness.
Fearlessly, the idiot faced the crowd Smiling Merciless, the magistrate turns 'round Frowning And who's the fool who wears the crown?