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In 1500, Trimalchio and his son Claudio were sent with several other thieves to spy on Niccolò Machiavelli. However, Trimalchio got separated from Claudio and the latter was wounded by Borgia crossbowmen and could not escape. Trimalchio was reunited with his wounded son when Ezio Auditore da Firenze brought him to the docks after saving him from being captured and killed by Borgia guards. Trimalchio was then instructed to take his son into hiding.