D&D General Rogue Subclass: Mastermind (Revised)

I like the mastermind concept, but it really doesn't have an identity or the proper feel.

What I'm thinking is that the framing device is to enhance the inspiration mechanic in the class and use it as the focus. They are more likely to acquire it, and when they expend it, it acts as a flashback that performs its normal function, but also provides additional benefits.

So here's a rough idea of how to make it work. Open to any feedback.

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Where others see only chaos, you see patterns. You’re the planner, the fixer, the manipulator who is always two steps ahead. Your schemes pay off in sudden flashes of foresight, represented by your mastery of Inspiration. You not only earn Inspiration more reliably than most adventurers, but you can spend it in dramatic “flashback” moments to twist the narrative in your favor.

3rd Level: Master of Intrigue (Revised)


You still gain the social mimicry features of the original Mastermind (disguise, languages, mimicry).
In addition:
  • Tactical Assessment: You can take the Study action (an Insight check contested by Deception or a DC set by the DM) as a bonus action against one creature. On success, you gain Inspiration and learn one of the following: AC, saving throw proficiencies, one resistance, or one vulnerability.
  • You can gain Inspiration this way once per turn, but only once per creature per combat.

3rd Level: Flashback Tactics

When you spend Inspiration, you may frame it as a flashback describing how you had prepared for this very moment. Doing so enhances the effect:
  • Flashback Setup: When you or an ally rolls with advantage from Inspiration, add your proficiency bonus to the roll as well.
  • If used on an ally, they may also move 10 feet without provoking opportunity attacks, representing pre-positioning.

6th Level: Contingency Planner

  • Flashback Counter: You can spend Inspiration as a reaction to cancel disadvantage on an ally’s roll or impose disadvantage on an enemy’s roll, explaining how you anticipated the outcome.
  • Strategic Gambit: Once per short or long rest, when an ally follows a course of action you suggested (DM adjudicates, but usually linked to Help, a plan you stated, or tactics you discussed), you gain Inspiration.

10th Level: Always Prepared

  • Flashback Equipment: When you spend Inspiration, you can reveal that you or an ally had a mundane item, tool, or potion of common rarity already prepared. (This can’t be used for magic items beyond common consumables, but can cover climbing gear, thieves’ tools, holy water, healing potions, etc.)
  • Calculated Risk: You gain Inspiration whenever you succeed on a risky play (provoking an opportunity attack, springing a trap, or winning a contested check where failure carries danger).

14th Level: Master Planner

  • Flashback Gambit: Once per short or long rest, when you spend Inspiration, you can significantly alter the scene. Options include:
    • Reposition one ally or enemy within 15 feet (“we planned for you to be here”).
    • Declare an overlooked escape route, cover, or hidden detail exists.
    • Force an enemy to reveal a hidden flaw (granting advantage on the next attack against it).
  • Additionally, if you aren’t surprised, you start combat with 1 Inspiration point.
 

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Interesting. Though inspiration has a changed a bit. It's now a reroll, not advantage. Thus stronger.
So I would simply it a bit.

Level 3:
As a bonus action, if you do not have inspiration, you gain inspiration. Once you use this feature you can't use it again until your take a short or long rest.

Level 6:
As a reaction when an ally within 30' rolls a die and you have inspiration, you can give the ally your inspiration. They can immediately use it on the trigger roll.

Level 10:
When you roll initiative, you gain inspiration. If you already have inspiration, you can give it to your ally as normal.

14: At the start of each turn in combat, you gain a inspiration. You may now have 2 inspiration durring combat.
 
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I’d say the most important thing the mastermind does is make the team more effective. Rather than giving themself inspiration, let them get information about a creature, and use the help action, as bonus actions.

Also at 3, let them drop a die of sneak attack and add it to the next attack roll made against the target by any ally.
 

so basically the rogue version of the warlord. that really does make sense and gives some fun design space to work from, especially if tied to inspiration, a tool that doesn't get used all that much.

I think I have a vision, ty kindly. :)

edit: and I think I even have a legally distinct, but fun name: Schemy Fingers. :D
 
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