|I really hate continuity errors.|
This article contains information that are canonical but may have been retconned, or contradicted by information that are also canon.
Ajay was a Reaper who went rogue and occasionally does "freelance". He moonlighted as a taxi driver.
Ajay was approached by Sam and Dean, for a way into Hell, so that they may complete the second trial to shutdown Hell. Here he reveals that that he took Bobby's soul to Hell instead of Heaven, under Crowley's orders. He agrees to the deal in return for a future favor from the brothers. He takes Sam into a graffiti filled room and together they enter Purgatory, instead of Hell. In Purgatory, he reveals that Sam himself has to find the portal that leads to Hell and warns him to be at the place they arrived, within 24 hours. He then vanishes.
Back on Earth, he is taking a lunch break when Crowley appears in his taxi. Crowley was informed by one of his demons, that Sam was spotted with Ajay. He demands to know, what deal had been struck between the two parties. Ajay reveals that the Winchesters wanted to enter Hell and that he was to pickup Sam from Purgatory in 17 hours. He is then killed by Crowley, with an Angel Blade so that Sam may be trapped in Purgatory.
- Ajay's name is Indian, but he sports the look of a Middle Eastern man. It's later revealed that Reapers can possess humans to appear on Earth and this discrepancy may simply be because the person he was possessing was Middle Eastern.