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There is no item called "pilot". The image of a pilot is for the item "Private Jet", which is available as a loot drop on the Make a deal with the Mexican cartel on the Boss tier in New York. Like all loot drops, it is also available as a random drop from fights, and through gifting by other players.
You might also mean one of the other plane items such as the Cargo Plane (loot drop from Storm the Airport in Cuba) or Private Helicopter (purchasable item in Cuba).
Or, you might mean Helicopter - an item which gives a 30 second reduction on energy regeneration times - and which is available as a reward for completing all three levels of the Consigliere tier in New York.
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