American Monster: The Trial Of Caleb Flynn24 Sep

Caleb Flynn Court Coverage Day 5: Wilhelm Uncovers WHAT From His Devices?!

Caleb Flynn's digital footprint moved to the center of the courtroom when Special Agent Joseph Wilhelm testified about the forensic extraction of Flynn's iPhone and Apple Watch data. Wilhelm said artifacts showed Instagram, GroupMe, ChatGPT and other apps were deleted from the phone on February 15, 2026, the day before Ashley Flynn was killed.

According to Wilhelm, the initial attempt to extract the iPhone was unsuccessful because of settings on the device. A different forensic tool allowed him to complete a full extraction, which he said revealed artifacts from incognito browsing.

Wilhelm also testified about data from an Apple Watch named @CalebApplesWatch. That included step counts, AirPods connectivity and a final recorded heart rate at 2:10:11 a.m. The extraction also recovered audio of a song Caleb wrote for Alleigha Botner, and that recording was played in court.

Caleb Flynn has pleaded not guilty in the murder of his wife, Ashley Flynn. Prosecutors allege he killed Ashley and staged the home as a burglary. His defense says Ashley was killed by an intruder and investigators rushed to judgment. For jurors, Wilhelm's testimony puts device-generated timestamps and activity into the timeline they are being asked to evaluate.

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