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Fallout 3 Game Add-Ons (DLC) Hints
How does that work?
1 of 8: When you challenge him, he'll give you a choice of weak melee weapons.
2 of 8: After you choose one, he'll give it to you and turn hostile.
3 of 8: Equip that weapon and whack him with it until he's dead.
4 of 8: You'd better not have any followers with you, since they'll attack Jack and violate the duel rules. You could lead your follower off and have him wait in a place out of sight, then return and do the duel.
5 of 8: TIPS: Use V.A.T.S. as much as you can, since Split Jack won't be able to block your attacks or hurt you until you exit V.A.T.S. Also, try challenging him while he's seated -- he may not get up right away, allowing you to get in some free starting whacks.
6 of 8: When you kill Split Jack, the other bandits will probably turn hostile and attack you instead of accepting you as their new leader. This won't always happen, but it often does (and karma doesn't seem to be a factor).
7 of 8: If combat is your preferred route, you should have Fawkes with you when you accept the duel so that he can help you roast the bandits. (You could also bring Dogmeat for some extra help.)
8 of 8: Or you could use the special mesmetron gun to turn the bandits against each other before the duel, making their elimination much easier and safer. (See the frenzy tip in the quest notes for the misc. quest "Strictly Business" in the main Fallout 3 hint file.)