This paper analyzes composer Aaron Cassidy’s 2014-2016 ensemble work The wreck of former boundaries, focusing on Cassidy’s compositional approach to sonically simulating interactive modes and sonic ideals featured prominently in mid-20th century recordings of free jazz artists such as Albert Ayler (Bells [1965]) and John Coltrane (Ascension [1965]). Because these musical conventions can be heard as socio-political simulacra in and of themselves, I argue that Wreck’s sonic simulations dissimulate the anti-hegemonic implications of the sound of free jazz, depicting spontaneous, hetero-original confrontations with socio-political constraint as symbolic and insubstantial. In my conclusion I argue that while an apparitional circulation of free jazz simulacra seems to de-politicize free jazz musical conventions, Wreck can be understood more precisely as critically analyzing the history of revolution. Heard through the interpretive lens of a broader history of hegemonic improvisations that absorb and displace open expressions of political defiance, Wreck appears to pessimistically reimagine free jazz as a novel form of symbolic, musical constraint.