|Dates||???? – 2013 (killed by Crowley)|
|Location||Kansas City, Missouri|
|Episode(s)||8.19 Taxi Driver|
Ajay (pronounced ah-JAY) was a rogue reaper, he was one of presumably many rogue reapers who transported souls in and out of Heaven and Hell for a price. According to Ajay smuggling mortals across the border is very risky.
Needing to sneak into Hell to rescue an innocent soul, Sam and Dean find out about rogue reapers from a crossroads demon and approach Ajay to take Sam to Hell. Ajay recognizes them and reveals that he is the reaper that took the soul of Bobby Singer to Hell on Crowley's orders when they burned his flask rather than Heaven where he belongs. Ajay agrees to transport Sam to Hell and him and Bobby back to Earth afterwards in exchange for the Winchesters owing him a favor in the future. Instead of taking Sam directly to Hell, Ajay transports him to Purgatory where there is a backdoor into Hell as he finds it too risky to travel directly into Hell with a Winchester. Telling Sam to meet him in exactly 24 hours at the spot where he dropped him off and giving him directions to the entrance before departing.
Ajay heads to his taxi with pizza, but is met by an angry Crowley in the backseat. Crowley has learned of Ajay's deal with the Winchesters from one of his minions who was watching and demands to know why Ajay did it. Ajay defends himself, saying he freelances and Crowley tells him he's not supposed to with the Winchesters. Scared, Ajay tells Crowley how he took Sam to Hell, but doesn't know why he wanted to go there. When asked how much longer until he has to pick Sam up, Ajay tells Crowley 17 hours. Crowley then kills Ajay with an angel blade so he can't pick Sam up at that time.
After learning of the route Ajay used to get Sam to Hell, Dean checks on him to find him dead in his cab and must turn to Benny Lafitte to get Sam out of Purgatory.