Someone not to meet on a dark night

Quote Originally Posted by Two-Faced Ivan

Two-Faced Ivan, The Dark Alley Terror

LE Desert Half-Orc Thug Fighter 2/Paladin of Tyranny 3/Menacing Brute 5/Twisted Lord 10

Abilities (With Racial Modifiers)
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Str 14
Dex 10
Con 14 (16)
Int 14 (12)
Wis 10
Cha 16 (increases here)

Build
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Level Class Base Attack Bonus Fort Save Ref Save Will Save Skills Feats Class Features
1st Thug Fighter 1 +1 +2 +0 +0 Bluff 4, Intimidate 4, Jump 4, Search 2(4), Tumble 4 Iron Will, (B)Run Skilled City Dweller: Ride>Tumble
2nd Thug Fighter 2 +2 +3 +0 +0 Bluff 5, Intimidate 5, Jump 5, Knowledge (Local) 2 (B)Martial Study(Distracting Ember) Bonus Feat
3rd Paladin of Tyranny 1 +3 +5 +0 +0 Bluff 6(2), Tumble 6 Hardened Criminal (Intimidate) Aura of Evil, Detect Good, Smite Good 1/day
4th Paladin of Tyranny 2 +4 +6 +0 +0 Bluff 7(2), Tumble 7 Divine Grace, Deadly Touch
5th Paladin of Tyranny 3 +5 +6 +1 +1 Bluff 8(2), Tumble 8 Aura of Despair, Divine Health
6th Menacing Brute 1 +6/+1 +8 +1 +1 Intimidate 9, Search 3 Shape Soulmeld (Fearsome Mask) Demoralizing Stare
7th Menacing Brute 2 +7/+2 +9 +1 +1 Bluff 9(2), Intimidate 10, Search 5 Resourceful Search
8th Menacing Brute 3 +8/+3 +9 +2 +2 Intimidate 11, Search 9 Sneak Attack +1d6
9th Menacing Brute 4 +9/+4 +10 +2 +2 Intimidate 12, Search 12, Sense Motive 1 Imperious Command Ruthless Cut
10th Menacing Brute 5 +10/+5 +10 +2 +2 Never Outnumbered, Intimidate 13, Search 13, Sense Motive 2 Making an Example
11th Twisted Lord 1 +10/+5 +10 +4 +2 Intimidate 14, Use Magic Device 8 Twisted Form
12th Twisted Lord 2 +11/+6/+1 +10 +5 +2 Bluff 10, Intimidate 15, Use Magic Device 15 Open Lesser Chakra (Brow) +2d6 Sneak Attack
13th Twisted Lord 3 +12/+7/+2 +11 +5 +3 Group Fake-Out, Bluff 16, Intimidate 16 (B)Improved Feint Improved Feint
14th Twisted Lord 4 +13/+8/+3 +11 +6 +3 Bluff 17, Intimidate 17, Search 17, Tumble 11 Peripheral Invisibility
15th Twisted Lord 5 +13/+8/+3 +11 +6 +3 Bluff 18, Hide 2, Intimidate 18, Move Silently 1, Search 18, Tumble 14 Terrifying Strike +3d6 Sneak Attack
16th Twisted Lord 6 +14/+9/+4 +12 +7 +3 Bluff 19, Hide 5, Intimidate 19, Move Silently 4, Search 19 Improved Demoralize
17th Twisted Lord 7 +15/+10/+5 +12 +7 +3 Bluff 20, Hide 8, Intimidate 20, Move Silently 7, Search 20 Twist Target
18th Twisted Lord 8 +16/+11/+6/+1 +12 +8 +3 Bluff 21, Hide 11, Intimidate 21, Move Silently 10, Search 21 Spectral Skirmisher +4d6 Sneak Attack
19th Twisted Lord 9 +16/+11/+6/+1 +13 +8 +4 Bluff 22, Hide 14, Intimidate 22, Move Silently 13, Search 22 Twist Perceptions
20th Twisted Lord 10 +17/+12/+7/+2 +13 +9 +4 Bluff 23, Hide 17, Intimidate 23, Move Silently 17 Twist Mind

Backstory
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From his beginnings as a petty crook on the city’s grimy streets, Ivan always had a mean streak in him. He was not as bloodthirsty as Mikhail the knife, or as strong as big Peotr, but he had an ability to influence others and a willingness to exert his will over weaker ones. He picked up a few skills on the streets, most of them related to violence and crime, but he was also educated in the code of the underground, of the alley, of the families. They were not held by the laws of the regular city folk, but their own were no less powerful for their simplicity. You could not work a normal job. You must obey your superiors. You will never report on any of your comrades.

This was a code that Ivan followed with fervent devotion. The crime lords had given him much by training him, and his dedication to them and the cause was absolute, and his faith guided his sword and protected him. He trained further in enhancing the natural ferocity of his tusked face into a truly daunting enemy. He had mastered his craft to the extent that he seemed to be masked by features far more unnerving than his own, which earned him his moniker.

When mad Alexei returned from his journey smuggling goods, he brought with him a new product from the scar, a bitter and nasty root more gnarled than seemed healthy for a plant, rumored to be capable of changing the consumer for the stronger, but also for the stranger. The crime lords were intrigued, but they wanted to see the effects for themselves. Ivan volunteered, as they knew he would, and sampled the vile substance. He felt slightly queasy, but not different, until the night following, when he was plagued by nightmares greater than he had ever inflicted. He awoke the next morning warped and malformed, but found no more discomfort than any other. His superiors concealed their repulsion and expressed excitement for the possibility, and ordered for more shipments.

As he consumed more Ivan’s mind altered in bizarre ways to match his body, and he began to learn to exert his own will enough to crumple the weak mind under him. He elevated from a threatening criminal to a legend whispered in every darkened alley, a hideous demon capable of striking from the shadows, moving even the bravest to terror, and working its way into the minds of the terrified to twist them to its dark purposes.

Level 5
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Desert Half-Orc will provide us with an in for menacing brute, and is pleasantly without charisma penalty. Thug Fighter provides some helpful skill points and an improved list, and we can use that second level feat to nab Distracting Ember, allowing us to flank enemies by ourselves, proper setup for things to come. Paladin of Tyranny allows us to put our Cha to use on our saves as well as smites. Aura of Despair effectively raises the DC of anything we use. Deadly Touch is useful when you need to bypass armor, and will serve as an excellent vehicle for sneak attack once that is online. Hardened Criminal prevents us from falling prey to our own trick, and will also allow us to take 10 on intimidate for more reliable results.
*If your DM rules that you must qualify for Twisted Lord’s bonus feat, replace Martial Study with Combat Expertise and move one point from Cha to Int, also put one more point in UMD.

Level 10
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Menacing Brute is a fascinating little PrC that pairs wonderfully with the SI. The first ability is pure gold, boosting Intimidate and keeping the target shaken for 5 more rounds! Resourceful search is useful for items that you wished you had but don’t have on you, and all it costs is time. Sneak attack gives us something to do with distracting ember, and don’t forget to deliver it on touch when enemies are being challenging. Making an example occurs any time you kill a creature, so you could easily see this operating multiple times in an encounter. If you wish you can use something like a bag of tricks to start combat with a kill for an opportunity to scare your foes.
Imperious Command is essential for an Intimidate build, the round of cowering means they’re susceptible to sneak attack and gives you time to move about safely to get in position, or heal up the team. The fearsome mask gives you a +2 insight bonus to Intimidate, which stacks with everything else, which is nice enough, but we’ll see it again.

Level 15
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With this many levels under our belt, and assuming a free flow of information among thieves in the Ebon Cabal, we have a high enough affiliation score to enter the SI. Twisted Form boosts Intimidate even higher, and helpfully boosts bluff as well. Now being able to feint as a move action means that you can do this at the end of a round, then get a full attack on the next round with the first being a sneak attack. Peripheral invisibility can be used to make a quick escape, move into position, or just to make a sneak attack, since defenders are always denied Dex by an invisible attacker.
Fearsome Mask is back with a brow bind, and it’s now the setup for a neat trick. It gives you a gaze that renders foes shaken for 1 minute. It works as any gaze, so they will likely be trying to avert their eyes to reduce exposure. If they do so, they’re not looking directly at you, so you can turn on peripheral invisibility! If they don’t avert their gaze, then you hit them with the shaken effect, and can follow it up with demoralize to frighten for 6 rounds. Never outnumbered means that you can hit multiple foes at once with the same demoralize for no extra effort. Group fake-out allows you to feint several foes for a small penalty, so make sure to use these in combat. Terrifying Strike is our third effect, which makes up for its 1 round duration by not offering any save. If they can be scared, they are once you hit them with a sneak attack from invisibility or after feinting. At this point your UMD modifier is enough to always succeed on using wands, so incorporate your favorites into your adventuring gear, there are many possibilities.

Level 20
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The final touches now. Your search modifier is high enough to always succeed on finding gear of up to 200gp worth, which can make for some decent gear in a pinch. It says nonmagical, so that likely means alchemical items are on the table, which can be a pretty good spread of consumables. Improved Demoralize plus Never Outnumbered makes for a pretty competitive move action. All three of the final abilities mention being next to a shaken foe, ask if they apply to frighten as once, or whether you should quit while ahead on foes. Twist target is great if anybody squishy has a guardian by them (remember animal companions will have poor will saves). Plus it can really distress your enemies to be told they weren’t “really” being controlled, since it isn’t a compulsion effect and won’t turn up on anything looking for it. Twist Perceptions means stunning, and a stunned target is a viable target for more sneak attack to refresh shaken, to keep their save to end the stun penalized. They also drop what they’re holding, so you can use this opportunity to take what they’re holding.
Twist Mind is the real interesting one. Because it takes a standard to control the target, you will likely use your move to either keep him in your aura to debuff, feint, or demoralize at your leisure. Or you can use this opportunity to become invisible or hide, to reduce enemy ability to mess with you. You can safely tumble through their square if you have to, and spectral skirmisher means that when someone misses when attacking you, you get an AoO, which is a sneak attack because you are invisible. Then the target is shaken, and setup for control. In terms of which rod to use, I’d suggest the open palm. The buckler is appreciated, and invisibility and obscuring mist are good setups for hiding and thus sneak attack.
You are always generating new targets for control, since if they can see you they are subject to the gaze, and if they can’t they will be sneak attacked for frightening attack.

Sources
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Desert Half-Orc, Paladin of Tyranny, Iron Will, Thug Fighter: srd
Menacing Brute: Races of Destiny
Martial Study: Tome of Battle
Shape Soulmeld, Open Lesser Chakra: Magic of Incarnum
Imperious Command, Terrifying Strike: Drow of the Underdark
Hardened Criminal: City of Stormreach
Spectral Skirmisher: Player’s Handbook II
Skilled City Dweller: Urban Class Features Enhancements