The Chalice of Dionysus was a well-documented item by historians and magicians, with passages about the item written in books. Though it was relatively famous, no one noticed that a college student at Hudson University calling himself Dion constantly had the artifact and used it as his personal cup. The only thing that most of the other students noted is that when they drank from it, they felt special and energetic for a day.
Despite not being a student at the university, Nate Heywood heard stories of the chalice and wanted to drink from it himself. One night, he climbed a ladder to the location of the Chalice just as it was placed on a windowsill during a party. However, Nate was caught trying to steal it, and in a panic, the ladder that supported him fell.
The Chalice was well documented in one of the books that Gary Green brought to the Legends as they researched how to become immortal long enough for at least two of them to use the Loom of Fate. John Constantine, flipping through a book, found the article, and made a passing comment about it; Nate saw the article as well and commented that he knew about the item. After telling the story from his past about attempting to steal it, Gideon alerted them that the Chalice was still at Hudson University in 2020. The Legends decided to get the artifact.
Upon arrival of Dionysus, both Clotho and Nate realized that they knew him: Clotho knew that he was the actual Greek deity from her past; Nate knew him as a student from his college years. Clotho approached her colleague and the two hugged, as Dionysus explained that his chalice only made Greeks immortal for a day, so her clique had to be "Greek" by pledging loyalty to a fraternity or sorority for the spell to work. This revelation frustrated Astra Logue, so she attempted to take the chalice; it was immovable without Dion's permission, causing the Legends to accept Dion's rules.
While Dion was having a party, Lita crept inside and found the Chalice, but it was immovable for her as well. When Dion learned from a spellcast Nate the intents of Clotho, Dion decided that he would not allow access to the Chalice.
Eventually, Sara Lance, leader of Delta Chi Sigma, challenged the undefeated Dionysus to a game of beer pong, winner gets the chalice; using her precognitive powers, Sara won. All of the Legends, except Zari Tarazi, drank from the Chalice and started to glow, as they were now immortals.
- Temporary immortality: Drinkers from the chalice receive immortality for twenty-four hours. The effect is usually seen by others as an ambient glow.
- Immovable: The Chalice cannot be lifted or even moved without Dionysus' permission; he never worried of it being stolen when it was not in his sight or lifted to be used without his knowledge.
- Accelerated healing: Drinkers heal quickly even from fatal wounds, as Ava Sharpe was shot in the head but survived and expelled the shell.