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Introducing: Into the Madness, new from Trevor Aaronson

February 20, 2025·38 min·3 clips

Trevor Aaronson investigates Bobby Cremo, a SoundCloud rapper who designed a twisted game around the Highland Park mass shooting.

Trevor Aronson introduces his Audible original series Into the Madness, a seven-part investigation of the 2022 Highland Park, Illinois Fourth of July parade shooting. The attack killed seven people and injured 48 others. The accused, Robert Cremo, known as Bobby Cremo or 'Awake the Rapper,' was a SoundCloud artist from the Chicago area. Prosecutors say Bobby confessed after his arrest, having been captured on surveillance footage walking to and from the rooftop where the shots were fired, dressed as a woman. His AR-15 style rifle was found on the sidewalk. Aronson's thesis is that the shooting was not ideologically motivated — Bobby was not a conventional far-right or Islamist extremist — but was instead part of an elaborate nihilistic game Cremo had designed, complete with cryptic videos, an online cipher, and a 27-page book of numbers. The chapter introduces Jamie, who first met Bobby at a club in Indiana in 2016 when he was 16 years old and performing as a SoundCloud rapper. She describes him as soft-spoken and quietly present, unlike many performers. Their relationship was sporadic and conducted almost entirely online. Jamie watched the Highland Park manhunt on live TV without initially realizing the suspect was Bobby, until she saw his distinctive eyes in a photo. After his arrest, Jamie contacted Bobby in jail and began recording over 48 hours of phone calls. Bobby's jail calls are described as evasive and cryptic, filled with mundane questions about dinner and weather, requests to hear music, and oblique references to government conspiracies and false flags. He maintains that the shooting was staged and that the FBI is behind it. The chapter also introduces Rachel Wachstein, a Highland Park activist who recognized the shooter as someone she had photographed at Stop the Steal rallies, dressed like Where's Waldo. Rachel begins investigating Cremo's digital footprint and initially concludes he was a far-right Trump supporter and anti-Semite. Aronson explains that much of Cremo's imagery was deliberately constructed to produce exactly this kind of misreading — it appeared ideological on first glance but was designed to mean different things to different viewers. Aronson introduces the 'doomer' theory of radicalization, arguing that nihilism — a total rejection of belief in anything real — can be as radicalizing as ideological extremism. He says Bobby's online activity in forums that shared violent videos was ironic and performative rather than sincerely ideological. Jamie eventually contacts Aronson because she believes Bobby was sending signals in his videos that she cannot decode. Aronson agrees to help investigate, though he tells the listener he sees a different story — one in which Jamie herself becomes the final player in Bobby's game.

As heard by us

A grim, reporting-driven setup that turns a mass shooting into a study of conspiracy and extremism.

Trevor Aronson opens a seven-part investigation into the 2022 mass shooting in Highland Park, Illinois, and keeps the focus from narrowing too quickly on the attack alone.

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Why you'd press play

Press play if you want a true crime lead-in that goes deeper than the headline.

Read the full recommendation in PlayNext →

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