Ajay

Ajay was a reaper who went rogue and occasionally does "freelance". He moonlights as a taxi driver.

Season 8
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 Bobby is in Hell instead of Heaven, under Crowley's orders. He agree 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. In Purgatory, he reveals that Sam himself has to find portal that leads to Hell and warns to be at the 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.

Trivia

 * Ajay's name is Indian, but sports the look of a Middlle Eastern man.