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After completing The Big Dig through siding with Bobbi No-Nose, John Hancock will intercept the Sole Survivor in front of the store area of Goodneighbor. Hancock is unhappy with the Survivor killing his friend and bodyguard Fahrenheit, and demands 1000 caps compensation, which can be reduced to 500 and 200 caps successively with increasingly harder speech checks, and tasks the Sole Survivor with confronting and killing Bobbi to retrieve those caps. Bobbi can be found at the Hawthorne Estate, apart from Bobbi herself there will be 2 initially passive turrets. There you'll have a talk with 3 potential outcomes, all of which will progress the quest:
- Kill her and get 425 caps off her body.
- Persuade her to give you the caps and get 375.
- Leave and get nothing.
If left alive, Bobbi will allow you to take the few items scattered around the estate (it will no longer be considered stealing).
Upon returning to Goodneighbor, Hancock will be waiting near the exit door on the second floor of the Old State House. Regardless of the action taken or dialogue options chosen, Hancock will respect your decisions and will not request the previously arranged payment. He'll remark that he's not the same as he had been years ago and that he needs to get back on the road again, to hone his edge.
After making a speech from State House balcony to the crowd of Goodneighbor, Hancock becomes available as a companion.