Pickman's Gift

Pickman's Gift is a side quest in Fallout 4.

Detailed walkthrough
Upon entering the gallery, you are met with multiple raiders, all of whom are searching for someone named "Pickman" and will attempt to kill you on-sight, presumably confusing you with the man in question. In the room immediately to the left of the entrance you will find the body of a raider that has the holotape Message to Jack on it. Listening to this holotape will give you your first clue about Pickman.

There are two different ways that one can enter the hidden tunnels, one is to find the hole in the wall on the third floor and use it to drop down into Pickman's basement, which then leads to the tunnels where you can hear someone calling for Pickman to come out of hiding. Alternatively, you can try to pick the master lock door which also leads directly to the same place. There is a rather high drop that you must jump down to continue exploring, though this will prevent you from backtracking, so caution should be taken if you're ill-supplied.

Continue through the winding tunnels while fighting off numerous raiders and a turret, remaining mindful of the ledges and water. When you arrive at a ledge at the end of the tunnel, you will find Pickman at gunpoint from several more raiders, including the leader, Slab. You can either save Pickman, let the raiders kill him, or kill them all. Even if you let the raiders kill Pickman, you'll still have to fight them afterwards to progress.

After killing all the raiders in Pickman Gallery, you can either loot his body in the event you or the raiders killed him, or simply speak with the man if he's still alive. Either option will grant you his key, upon which the quest will be added to your Pip-Boy.

If Pickman is spared, he will tell you to take a closer look at his painting "Picnic For Stanley". After exiting the house via the tunnel exit nearby, make your way back and re-enter through the front door. On this ground floor in the Northwest corner is a painting of a man with his eyes removed. Activate it to reveal Pickman's safe, which can be opened with the key obtained from Pickman. Collect his gift and complete the quest.

Bugs

 * If you pick the lock on Pickman's safe behind the painting and loot it taking Pickman's Blade before saving or killing Pickman and then encounter Pickman, he will still give you the key and you will have the same conversation options triggering the quest. After deciding Pickman's fate, and returning to his safe, it will show nothing in it and still unlocked from the way you left it earlier. The quest will still be in your log though, to fix this use the transfer option and place the Pickman's Blade back in the safe, exit the safe, re-enter the safe and retrieve the blade again. This will mark the quest as completed in your log and award you experience.

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