Diplomacy and Blackmail Gestalt (3.5e Optimized Character Build)

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The basic idea for this build is using the non-standard Merchant and Bard classes in a Gestalt fashion. Trade Knowledge and Bardic Knowledge stack meaning by level 20 you'll have a very large mod for your random blackmail findings, and at your diplomacy checks will be so high that no one will be able to question you.


SRD:Bard, Merchant(DnD Class), Player's Handbook, and things off this site.


Cloak of Charisma +6, Headband of Intellect +6, Tomb of leadership and Influence +5, Tomb of Clear Thought +5


Starting Ability Scores (Before Racial Adjustments): Str:10 Dex:13 Con:8 Int:14 Wis:12 Cha:15 Race (Templates): Ikasus

Starting Racial Traits: -2 Str, -2 wis, +2 Int, +2 cha

Scores after Racial Adjustments: Str: 8 Dex: 13 Con: 8 Int: 16 Wis: 10 Cha: 17

The level 4 point goes into Cha, the other 3 go into Int giving you a end result of: Cha 18 and Int: 19

ECL Class Base
Attack Bonus
Saving Throws Feats Class
Fort Ref Will
1st Bard(1)/Merchant(1) +0 +0 + 2 +2 Skill focus Diplomacy, Obscure Lore Bardic Music, Bardic Knowledge, Countersong, Fascinate, Inspire Courage +1, Skill Focus, Equipped, Trade Knowledge Skills: Bluff(4), Diplomacy(4), Knowledge(noble)(4), Sense motive(4)
2nd Bard(2)/Merchant(2) +1 +0 +3 +3 Contacts +1, Bribery, Uncanny Barter +1 Skills: Bluff(5), Diplomacy(5), Knowledge(noble)(5), Sense motive(5)
3rd Bard(3)/Merchant(3) +2 +1 +3 +3 SPECIALIST [Diplomacy] Connoisseur, Inspire Competence Skills: Bluff(6), Diplomacy(9), Knowledge(noble)(6), Sense motive(6)
4th Bard(4)/Merchant(4) +3 +1 +4 +4 Trade routes Skills: Bluff(7), Diplomacy(10), Knowledge(noble)(7), Sense motive(7), Cha = 18
5th Bard(5)/Merchant(5) +3 +1 +4 +4 Identify item Skills: Bluff(8), Diplomacy(11), Knowledge(noble)(8), Sense motive(8)
6th Bard(6)/Merchant(6) +4 +2 +5 +5 Negotiator Suggestion, Leadership, Uncanny Barter +2 Bluff(9), Diplomacy(12), Knowledge(noble)(9), Sense motive(9)
7th Bard(7)/Merchant(7) +5 +2 +5 +5 Bluff(10), Diplomacy(13), Knowledge(noble)(10), Sense motive(10)
8th Bard(8)/Merchant(8) +6/+1 +2 +6 +6 Inspire Courage +2, Find Treasure Bluff(11), Diplomacy(14), Knowledge(noble)(11), Sense motive(11), Int = 17
9th Bard(9)/Merchant(9) +6/+1 +3 +6 +6 Improved Synergy Inspire Greatness Bluff(12), Diplomacy(15), Knowledge(noble)(12), Sense motive(12)
10th Bard(10)/Merchant(10) +7/+2 +3 +7 +7 Bluff(13), Diplomacy(16), Knowledge(noble)(13), Sense motive(13)
11th Bard(11)/Merchant(11) +8/+3 +3 +7 + 7 Contacts +2 Bluff(14), Diplomacy(17), Knowledge(noble)(14), Sense motive(14)
12th Bard(12)/Merchant(12) +9/+4 +4 +8 +8 Flashes Of Brilliance Song of Freedom Bluff(15), Diplomacy(18), Knowledge(noble)(15), Sense motive(15), Int = 17
13th Bard(13)/Merchant(13) +9/+4 +4 +8 +8 Uncanny Barter +3 Bluff(16), Diplomacy(19), Knowledge(noble)(16), Sense motive(16)
14th Bard(14)/Merchant(14) +10/+5 +4 +9 +9 Inspire Courage +3 Bluff(17), Diplomacy(20), Knowledge(noble)(17), Sense motive(17)
15th Bard(15)/Merchant(15) +11/+6/+1 +5 +9 +9 Practice Makes Perfect Inspire Heroics, Trading expertise Bluff(18), Diplomacy(21), Knowledge(noble)(18), Sense motive(18)
16th Bard(16)/Merchant(16) +12/+7/+2 +5 +10 +10 Bluff(19), Diplomacy(22), Knowledge(noble)(19), Sense motive(19), Int = 18
17th Bard(17)/Merchant(17) +12/+7/+2 +5 +10 +10 Contacts +3 Bluff(20), Diplomacy(23), Knowledge(noble)(20), Sense motive(20)
18th Bard(18)/Merchant(18) +13/+8/+3 +6 +11 +11 Skill Mastery Control trade route, Mass Suggestion Bluff(21), Diplomacy(24), Knowledge(noble)(21), Sense motive(21)
19th Bard(19)/Merchant(19) +14/+9/+4 +6 +11 +11 Bluff(22), Diplomacy(25), Knowledge(noble)(22), Sense motive(22)
20th Bard(20)/Merchant(20) +15/+10/+5 +6 +12 +12 Master trader, Inspire Courage +4 Bluff(23), Diplomacy(26), Knowledge(noble)(23), Sense motive(23), Int = 19

Other Components[edit]

<- anything not covered by the previous sections ->


Once you apply the tombs and items your Int is now 30, and your Cha is 29 Giving you mods of 10 and 9 respectivly.

This Build works by giving you an insane bardic knowledge check for blackmailing, and a diplomacy check so high that you can talk your way out even if you get caught.

Your bardic knowledge check (since it stacks with trade knowledge) is now 1d20+53. Even if you roll a 1 you still have enough knowledge to pick up "Extremely obscure" knowledge that could be used for blackmail.

And now thanks to your feats and skills your diplomacy check (since you can take 20 now is) 20+10(int)+9(cha)+26(rank)+15(synergy)+6(skill focus and skill mastery)+2(negotiator)+3(practice makes perfect)+20(flashes of brilliance) this in total gives you a diplomacy check of 111. This is way more than enough to true any hostile person into helpful, even with a -10 rush mod.

Munchkin-Size Me[edit]

<- Take it to the next level ->

Side Notes[edit]

This is not to be used, it's mostly just for show, if you use it, I'm sure most people in the campaign will want to hurt you.


It needs to be able to speak so it won't work on things that can't talk.

DM Counters[edit]

Send the tarrasque, undead, or constructs, since they can't talk.


This uses things off Dandwiki.

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