All the NPCs in the resort area north of Ungoro.
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Lore-wise probably Velen or one of the dragons.
In the writing, I would say Thrall or Saurfang.
Tezran, the Master of Fate. People gamble millions with this guy. Think of all the longbois this guy could have bought.
If Thrall’s stupid Jaina is too.
People are instinctively attracted to those of a similar intelligence.
Were we going to win though? Up to this point we have had our asses kicked, lost Rasthakan and most of the Zandalari Navy and honestly we were being chased down by a whole group of Alliance ships and basically the only reason they didn’t wipe us out was because Azshara opened the sea and let it swallow everyone.
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There are a few contenders. Azshara seems up there, but Jaina outfoxed her. Medivh might be a bit more stable with Sargeras being occupied.
i definitely agree that sylvanas is the smartest…she outsmarts everyone, including her own faction, by herself.
furthermore she’s also a top military leader and individual fighter
Sylvanas can’t be. Because someone that’s been around as long as her should know, when you piss off all of Azeroth, that usually signs your death warrant.
She’s arrogant, and arrogance is the greatest stupidity.
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Medivh is for sure super smart.
Kiro and Nisha 
N’zoth. Despite being the weakest old god canonically, he’s lived the longest and was the only one to truly break his confines.
He manipulated Azshara, he manipulated Deathwing, he manipulated The Emerald Dream, he’s probably luring Sylvanas into a false sense of security.
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Grizzek Fizzwrench and Sapphronetta Flivvers.
They put aside the rivalry between factions and tensions between the races to fall in love, get married and disappear (for the most part).
Chief Telemancer Oculeth.
Test…Observe…Repeat!
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yeah but sylvanas is smart and good at surviving by herself…she has a lot of solo survival skills from her days spent in the wilderness.
if she does meet her end, it will be because she chose to reveal herself, not because she they found her.
she will meet her end on her own terms if it comes to that
Obviously the smartest person in Azeroth is Gamon.
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Shocking development.
Are we talking intelligence or knowledge?
Kil’jaeden should get a nod here. So many of Azeroth’s conflicts can be traced back to him.
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Hogger. He’s truly a mastermind.
Sassy Hardwrench
It’s because of her that the goblin hero was able to get things done. She may have been the PC’s assistant, but she was the brains behind the operation. Then after the starting zone she got her own piece of land and her own business. That’s pretty awesome!