Good Stealth/Fighter Build

[Death_Lord12]

I need help making a lvl 20 build that can be both stealthy and a good fighter for an NPC. Basically I'm looking for a ruthless killing machine that can easily hide in the shadows when he wants to. He is going to be the leader of a gang/thieves guild and also be a kind of assassin, though that doesn't mean he has to use the assassin prestige class. Any suggestions on class(es), feats, race, template(s), gear, etc. are appreciated.

Any source is allowed.

Thanks in advance.

[rrwoods]

I'm biased, but it sounds like a whisper gnome swordsage is right up your alley.

[Honest Tiefling]

I'm biased, but it sounds like a whisper gnome swordsage is right up your alley.

I'm going to second this, unless Swordsage is banned for some reason. Look up the Shadowhand school and tell us what you think of it.

[Extra Anchovies]

Slayer (http://www.d20pfsrd.com/classes/hybrid-classes/slayer) 20. It backports nicely to 3.5 if you're not running pathfinder.

[Elder_Basilisk]

Slayer (http://www.d20pfsrd.com/classes/hybrid-classes/slayer) 20. It backports nicely to 3.5 if you're not running pathfinder.

If you're willing to backport Pathfinder, Vigilante 20 would work very nicely too. (And it would provide him with mechanics for his cover identity and safe houses too).

[Rebel7284]

A bunch of options.

Telflamar Shadowlord can be a fun sneaky build at high levels. Teleport in and full attack, teleport out.

Ruby Knight Vindicator gets armored stealth and due to a cleric base can fight super well.

Taking a bunch of levels in Thug Fighter variant gives you exactly a fighter with more skills.

Psychic Rogue can be pretty good with a few expanded knowledges.

Factotum focuses on all the skills, but can fight well too, especially if Iajitsu Focus is allowed.

Rogue/Swashbuckler with Daring Outlaw works for this consept too.

Bard/Warblade with song of the white raven does this nicely too.

[ExLibrisMortis]

I second whisper gnome swordsage and Telflammar Shadowlord (there's also the Crintri Shadow Marauder). Telflammar Shadowlord requires a certain template, which can be purchased for 10.000 gp. This template then provides a whole bunch of shadow-themed SLAs, which don't work in areas of bright light.

The TSL 4 ability allows you to full attack at the end of any teleport, so it will allow three full attacks per turn by default (swift, move, standard - use Shadow Hand maneuvers, for example).

[Sian]

I'd be a bit offbeat and suggest Rogue/Scout with Swift Ambusher

[Seppo87]

Gonna go classic here

Rogue2/Fighter(hit-n-run)2/Swashbuckler3/Invisible Blade 5 (the revised version with fixed entry requirements)/Warblade2/Swordsage2/Battle Trickster 3/Uncanny Trickster 3
(not necessarily in this order, check feats prereq and build accordingly)

Note: Use Uncanny Trickster to advance a martial adept class

Important feats:
Shadow Blade, Knowledge Devotion, Craven, Darkstalker, Two-Weapon Fighting (only the first, use a glove of the balanced hand therafter), Daring Outlaw, Staggering Strike

BaB 18, sneak attack 8d6+20

Note on maneuvers:
Use Warblade for the ones you are sure you'll need often, Swordsage for the situational counters (and the access to shadow hand obviously)
Do not select single strikes obv (except perhaps mountain hammer, to break walls) choose maneuvers that help the fighting style of the character

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However, if you can port Pathfinder, I'll second Slayer20

[bloated glutton]

fire elf factotem 3/warblade 8/eternal blade 9.

important feats: education, knoledge devotion, robillars gambit, iron heart aura, storm guard warrior,
power attack, font of inspiration.
bab 19

smart and skillfull leader.
stealth skills, iaijutsu focus plus battle clarity vs flat-footed enemies.
you get intelligence to attack roll, damage rolls, skill checks, ac, saves and more.
provoke attacks of opportunity to channel the storm with stormguard warrior feat (+4 atk, +4 dmg).
using time stands still and eternal island, make 3 full round attacks.
iron heart aura and white raven tactics make this npc great in an encounter with minions at his disposal.
change maneuvers for a different boss fight every encounter.
great defense and maneuverability make for a great recurring villain.

[Gildedragon]

Use the dark creature template
If swordsage is a no go:
Urban ranger might be the best idea

[Death_Lord12]

Telflammar Shadowlord looks cool, but I think the Slayer 20 suggestion would fit perfectly for what I have in mind.

Thanks for the help.