Both Haknir Deathbrand and Velehk Sain were known to have dealings with Daedra, but you'll best them both!
Daedric Quests: Any and all you choose! A chance to make a pact with a Daedric lord in exchange for power isn't one to overlook. Lights Out! Take out another band of pirates, steal their hidden treasure!. In My Time of Need Complete this one early, siding with Saadia to get a load of scimitars for you and your crew!. 
Forgotten Names Help the Dremora Pirate Velehk Sain free himself and gain a map to his buried treasure!. No Stone Unturned Completion of this quest in conjunction with the perks Golden Touch and Treasure Hunter will greatly enhance your loot!. The Black Star: The black star is a great asset for recharging your scimitars!. 
The Taste of Death: Acquire Namira's ring, which enables you to empower yourself by feasting on the life force of fallen foes. Blood on the Ice Gain Mannimarco's ancient amulet and utilize its dark empowerment. Lost to the Ages A great treasure hunt, which provides your pirate king crown. Deathbrand Aside from the awesomeness of hunting down one of Tamriel's most notorious pirate's treasure, you gain your main weapons The legendary scimitars Bloodscythe and Soulrender. Dragonborn Become Herma Mora's new champion and seek out the knowledge and power of his black books.Īny quest where you're in search of some kind of treasure!. TG offers all kinds of opportunities to make some septims, but it's worth it to join even just to unlock the fences. Thieves Guild This character strives for power, because power makes money. Dark Brotherhood If murdering for big septims isn't enough, you get a sweet unique scimitar out of it! Also, the mini treasure hunts given from the hostages in the torture room make for some piratey fun!. Avoid this, and you have ANOTHER crew member. 
After the armor is acquired, feel free to bail, or stick through a bit longer till you have Serana following you to her family's castle.
Dawnguard This quest is only initiated to get your captain's armor. The Main Quest up to Alduin's wall, in order to keep Delphine and Esbern as followers. The College of Winterhold is your original destination, but gaining entrance is all that's really necessary, to gain access to the Master Conjuration Ritual quest from Phinis Gestor.
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