Psycho Pirate vs. Mastermind: A Battle of Illusions and Manipulation

Introduction

In this episode of the Dynamic Duel podcast, the battle takes a psychological turn as we pit two of the most manipulative villains in comics against each other: DC’s Psycho Pirate and Marvel’s Mastermind. Both characters have the power to distort reality—or at least the perception of it—making for one of the most unique matchups we’ve covered. Who would win in a fight between these two illusionists? That’s what we set out to determine using our Monte Carlo simulations.

Breaking Down the Characters

Psycho Pirate is a villain closely tied to DC’s Justice Society of America. Originally, the name was used by Charles Halstead, but the more infamous version is Roger Hayden, who wields the mystical Medusa Mask. This artifact grants him the ability to project and manipulate emotions in others, making him a dangerous opponent who can turn allies against each other or induce despair and insanity in his foes. He has played a pivotal role in major DC events like Crisis on Infinite Earths, where his power even influenced entire universes.

Mastermind, on the other hand, is an X-Men villain who possesses the mutant ability to cast telepathic illusions. These illusions affect all five senses, making them incredibly convincing, even to those who know they aren’t real. Mastermind has used his powers to manipulate the X-Men on several occasions, most notably in transforming Jean Grey into the Dark Phoenix while working with the Hellfire Club. His abilities allow him to create entire realities within his victims' minds, leading them to act against their own best interests.

Speculating the Battle

When two illusionists go head-to-head, the battle becomes one of deception and counter-deception. In the speculation segment, we imagined a scenario where Psycho Pirate attempts to manipulate Mastermind by inducing fear. However, Mastermind counters by creating an illusion of darkness, preventing Psycho Pirate from seeing him. This back-and-forth exchange continues as both characters attempt to gain the upper hand through mind tricks and psychological warfare.

One of the more creative moments in our imagined battle involved Psycho Pirate using his Medusa Mask to create illusions of tickling feathers, forcing Mastermind into uncontrollable laughter and breaking his concentration. In retaliation, Mastermind cast an illusion of a medieval torture chamber, making Psycho Pirate believe he was being stretched on a rack. Ultimately, the fight escalates to a massive illusion battle, with both characters conjuring up entire teams of superheroes—Justice Society projections from Psycho Pirate and an illusion of the X-Men from Mastermind.

The Results

As always, our battle outcomes are determined by running 1,000 Monte Carlo simulations using character statistics. In a very close match, Psycho Pirate emerged victorious, winning 51.7% of the simulations compared to Mastermind’s 48.3%. While Mastermind had an advantage in range and versatility, Psycho Pirate’s ability to directly control emotions proved to be the deciding factor. The Medusa Mask’s power to manifest deeply personal and realistic fears made it difficult for Mastermind to maintain his illusions effectively.

Final Thoughts

This was one of our most difficult matchups to break down, as both characters rely heavily on deception rather than direct combat. The close win percentage reflects how evenly matched they are, making this one of the most fascinating duels we’ve run. Let us know what you think—did the right character win, or do you think Mastermind should have come out on top?

Listen to the full episode here: Psycho Pirate vs. Mastermind.