After he used his latest shipment of military spying equipment, Penguin kept surveillance over the crime lord. Penguin attempted to murder Black Mask with a handful of his crew within his safe house at Lacey Towers, only to find Black Mask's girlfriend, Tiffany Ambrose, dead and hanging from a chandler, and a Decoy Black Mask dead as well. Disturbed by the gruesome fashion in which the murders were committed and annoyed after he learned that it wasn't actually the real Black Mask, Penguin left the room and building after he unknowingly left his fingerprints at the crime scene. Penguin was initially believed to be the killer by the GCPD, but thanks to a few bribes he was never convicted.
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