When he was a child during the 1950s, Oliver developed psychic abilities and worked at a carnival from at least the age of ten using them. The Men of Letters found him and trained him in the use of his powers before Abaddon destroyed them. At some point, Oliver isolated himself from other people as all the voices in his head got to be too much for him.
In 2015, needing to contact Bobby Singer in Heaven, Sam Winchester and Castiel tracked down Oliver and demanded his help. Oliver was shocked to meet Castiel, an angel and was shocked to learn Heaven had a jail but reluctantly agreed to help after a threat by Sam and performed a séance, allowing them to contact Bobby in Heaven.
Powers and Abilities
Oliver was a powerful psychic.
- Telepathy - Oliver was able to read Sam Winchester's thoughts with ease though he only got an impression of colors when trying to read the angel Castiel's.
- Mediumship - Using a séance, Oliver was capable of communicating with the dead, even those in Heaven, something no other psychic displayed before.
- He was an atheist until he met Castiel.