DMing for a Mastermind Rogue

[Sparky McDibben]

So, I'm starting up an intrigue-centric game soon that will feature a Mastermind rogue as the player in a single-player campaign, starting at level 1 and going to level 20. I'm looking for ideas on ways to highlight her abilities in-game, let her get in over her head, and evolve the narrative.

Has anyone either run or DMed for a Mastermind rogue, and if so, what are some things I should watch out for? Have you put one in a good trap, either socially or physically? Do you have any suggestions?

[Kane0]

a good sidekick would probably be really useful, someone they can use their bonus action help on, bounce ideas off and cover abilities that they themselves have trouble with. A watson to the holmes so to speak.

[iTreeby]

The tool description section in xanathar's is basically full of mastermind fodder. I recommend that you use factions frequently so that when spy vrs spy situations arise the player can choose which they support.

[ImproperJustice]

Give them some one on one NPC interactions, similar to how cold war spies would interact.
Have folks engage in tit for tat conversations with everyone trying to recruit each other.