In Act 1, the Winions first appear in the song “Open Arms,” when Odysseus and Polites seek food for their army. The creatures initially seem hostile, but quickly become cooperative when threatened. They offer the glowing lotus fruit—later revealed by Odysseus to be dangerously mind-controlling. Their seemingly harmless offer marks a turning point: they are not just silly background characters, but beings whose actions have lasting, dangerous effects.

The Winions reappear in "Keep Your Friends Close" during Odysseus' meeting with Aeolus. Acting as Aeolus' sidekicks, they gleefully carry the wind bag aboard Odysseus' ship. Out of mischief (or perhaps deeper malice), they spread lies to the crew, saying the bag contains treasure. This leads the men to open the bag, unleashing Poseidon's storm and destroying their chance at returning home. Once again, the Winions are shown as chaotic agents of misdirection, meddling with fate under the guise of whimsy.

In Act 2, the Winions return in the song “Dangerous” alongside Hermes, once again delivering Aeolus’ wind bag. Here, they appear more serious—Hermes warns Odysseus not to open it again, and the Winions echo the warning. This is also where we meet the Princess Winion, the only named female Winion and a rare variation in their otherwise identical group. Despite their previous mischief, the Winions now act as guides, suggesting a shift in role from playful saboteurs to reluctant allies. Whether symbols of trickery or fate’s agents, the Winions’ presence adds a layer of unpredictability that haunts Odysseus at every turn.