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Fallout: New Vegas Hints
Kill Caleb McCaffery.
1 of 3: Enter the Strip and follow the quest arrow to Caleb McCaffery. (If you've never been to the Strip yet, see the "Ring-a-Ding-Ding!" main quest's first objective for info on how to get in.)
2 of 3: Talk to Caleb and tell him that he can go free if he gives you his hat and a share of the caps. If you can pass the Speech 40 check that comes up, you'll get his hat and 57 caps without a fight.
3 of 3: If you can't do that, or want more caps, use other dialogue options to get him to turn hostile. After he's dead, you can loot him to get his hat and other items.
