The Magician is perhaps the trump where a Harlequin is most at home. He gets free rein to bedevil, bewilder, and swindle.

He is surrounded by four pestering imps lovely children and dizzying streaks of red. Maybe they are in league – the Magician’s plants in the audience. Or not. Will he succeed in tricking his audience out of their coins, or will they vex him so that he gives up?
To me, his apparently one-legged stance prefigures the Hanged Man – a warning to any would-be street charlatans.
The Bolognese deck, giving the Magician a small audience, shows him more clearly as a street performer than even the famous Tarot de Marseille pattern.

20th century occult depictions of the Magician (Waite-Smith, Thoth, etc.) elevate his status, giving him the power of manifestation and a stately mien. While Etteilla’s writings prefigured this trend, equating the Magician with the legendary Hermes Trismegistus1, the divinatory meaning of the card is decidedly less glorified. Sickness, pain, and madness – this conjuror is an evil influence.

In my drawing, these meanings are embodied in the tormenting horned Harlequin-lings dressed in red. They make a great team, there is one to disturb each of the four humors.
The little demons are also inspired by this print of Harlequin complaining to Pantalon about his children. I don’t know where it came from, it’s been hanging out on my camera roll for a while.

It may be a negative card, but it has a certain malicious fun to it! Maybe it is less helpful for those who use tarot as a reflective tool, but fortune-telling would not be the same without the flavor of such grim cards.
Keywords (translated from Julia Orsini)
Upright: illness, disease, mania, Illness of body, of soul, or of mind, bad state of health or of affairs, disruption, infirmity, pain, poison, epidemic, plague, gangrene, anxiety, death throes, ill, displeasure, damage, sorrow, woe, misfortune, disaster
Reversed: illness, indisposition, inconvenience, headache, heartache, illness of lethargy, unhappy position, disgrace, unpleasantness, worry, melancholy, affliction, medicine, remedy, charlatan, empirical medicine, mage
Notes
1 Etteilla is responsible for the popular and misguided notion that the tarot was really a book authored by Hermes Trismegistus, or the god Thoth. I will still take Etteilla over Crowley anytime.