The pirate assassin bugs, also known as corsairs, are a medium-sized subfamily of assassin bugs with over 340 species worldwide. Individuals in the subfamily exhibit striking antipredator aposematic color patterns, which should not be taken lightly as species of Peiratinae reportedly inflict the most painful defensive bites of all reduviids and are well-defended chemically by the secretions from the dorsal abdominal and metathoracic glands. Several aposematic patterns within Peiratinae occur in different genera suggesting a complex evolutionary history of color patterns in the group. Along with their striking appearance, their mating behaviors are unique, being one of the only reduviids with asymmetric male genitalia and accordingly modified mating position. Our objectives are to infer the first robust phylogenetic hypotheses across Peiratinae using ribosomal, mitochondrial (mt), and anchored hybrid enrichment (AHE) loci and use this hypothesis to reconstruct the ancestral condition of certain color patterns and male and female genitalic characters, while comprehensively documenting the unique phenotypic diversity in this group.