Week 2 of Flynn Trial continues with testimony, personal texts, prosecution evidence

A timeline of Week 2 in the Caleb Flynn murder trial, with highlights for each day of the proceedings.

Testimony continued in the first week of the Caleb Flynn trial, covering many aspects of the prosecution’s case against Flynn. He has been charged with aggravated murder, murder, felonious assault, tampering with evidence and intimidating a witness, victim or attorney.

Monday

On Day 2 of testimony, the state spent the day on the crime scene and autopsy. Flynn cried again as photos and descriptions were shown; Ashley’s family left the courtroom before the most graphic images. Court adjourned around 4:15 p.m.

• BCI Special Agent David Hammond walked jurors through the house. He said the garage side door Flynn claimed an intruder used did not look like a typical forced entry: no pry marks on the frame, the latch still worked, and wood chips were inside the garage, as if the door was damaged while it was already open. Ashley was found in bed in pajamas on her left side; Hammond said her position was consistent with being asleep or lying still when she was shot. Two 9mm casings were on the bedroom floor. Hammond said there was no blood on Flynn’s clothing and no murder weapon. Crime-scene tech Holly Ryczek said a bedroom light switch tested presumptive for blood; master-bath sink and shower drains did not.

• Forensic pathologist Dr. Bryan Casto, who did the autopsy the next morning, testified Ashley was shot twice behind the right ear. The wounds were close together and followed parallel paths out the front of the skull; one bullet exited and re-entered her left elbow, which had been under her head. Cause of death was multiple gunshot wounds to the head. Range of fire was “indeterminate” — no soot or stippling. Toxicology showed Prozac and elevated levels of melatonin. Photos of the uncleaned wounds showed hair, blood, and brain matter. Detectives also described searching the house, attic, vehicles, woods, and storm drains and collecting tools from the home. The gun was never found.

• The defense used cross-examination to underline what was missing: no firearm, no determined shooting distance, and no foreign DNA or clear forced-entry marks.

Tuesday

Tuesday, September 22 was Day 3 of testimony in the Caleb Flynn murder trial in Troy. The day’s focus was family, money, and forensics rather than the affair texts that dominated later in the week.

• Ashley’s mother, Jill Smith, gave the most discussed testimony. Days after the shooting, Flynn took the couple’s two daughters for a walk. When they returned they looked nervous. Smith marched one girl to Flynn and told him she was afraid to tell the truth; he said she should. The girls still seemed “super nervous” afterward. Smith also described Flynn telling the girls their mother was in heaven and them screaming and clinging to him. Ashley’s sister, Kayla Keyt, said the older girl was “not surprised” when she learned who the mistress was. Their father, Todd Smith, said the dogs not barking never made sense to him.

• Police and BCI witnesses covered finances and physical evidence. Flynn was the sole beneficiary of a $100,000 life insurance policy on Ashley; the couple also had a joint savings account with more than $84,000. DNA consistent with Flynn was found on a garage knob, truck console button, a stain in his shorts, a bedroom light switch, and a bathroom sink. Prints matching him were on a bedroom door frame and refrigerator. Two 9mm casings came from the same unrecovered gun. An ATF dog search found nothing, and a neighbor said her cameras and dogs registered no unusual activity that night.

Wednesday

On Day 4 of testimony, Tipp City Det. Brad Kline and other officers said the garage door looked damaged from the inside, with the knob and wood chips inside the frame and no typical pry marks outside. A Dayton officer assigned to the FBI task force, who has kicked in more than 100 doors, said it did not look like a normal forced entry. A canvas of the neighborhood found no video of anyone outside the house before police arrived.

• The afternoon belonged to Alleigha Botner, Flynn’s former mistress. She said she met him as a church intern when she was about 20, the relationship turned sexual in 2024, and they exchanged more than 107,000 text messages. They got matching lightning-bolt tattoos; hers is on her arm, his under his arm where Ashley “would not see it.” She testified he called Ashley names, said he hated her, and talked about wanting her “dead” or “gone.” She said he told her he would divorce Ashley on February 16 — the day Ashley was killed.

• Asked how she feels about him now, Botner said, “I hate him,” because “I believe that he murdered his wife.” Flynn, who had cried earlier in the week, sat stone-faced. She was still on the stand when court recessed.

• Look for more reporting in the Tipp Gazette and on our website (www.tippgazette.com) as the Caleb Flynn trial continues.

Thursday

On Day 5 of testimony, Alleigha Botner finished nearly seven hours on the stand over two days. Prosecutors had her read from stacks of printed messages bound in 34 large printed and bound books detailing over 107,000 text messages between her and the defendant.

• The sharpest moment was a July 2025 exchange she sent: “I want to kill her, Caleb.” She broke down reading it and said she did not mean it. Flynn’s reply, she read, was “That makes two of us.” Jurors also heard his August 2025 text about staying up until 4 a.m. “thinking of ways to kill her and not go to jail,” plus the night-before messages in which he said he chose Botner and that “actions will come tomorrow.”

• On cross-examination the defense pressed that Botner understood those “I’m free” and “taking action” texts as a plan to divorce Ashley, not kill her. She agreed she never took them as a murder plot. Counsel also highlighted her jealousy, her deadlines for him to leave, and that Flynn sometimes lied to keep her calm. She said she was offered nothing in exchange for testifying.

• After she was excused, BCI cyber agent Joseph Wilhelm began walking through data from Flynn’s phone and other devices, including apps that had been uninstalled. The jury then heard two AI-generated songs Flynn wrote for Botner.

Friday

Day 6 of testimony in the Caleb Flynn trial continued with BCI cyber agent Joseph Wilhelm, who finished his testimony about his investigation of the family’s cellphones, laptop, and Flynn’s Apple Watch.

• Among the points: Botner’s iPhone logged no steps from about 12:13 a.m. to 9:30 a.m. on February 16. FBI Special Agent Andrea Kinzig testified that emails from a paid service Flynn used to monitor Instagram had been deleted from his Gmail and that a tip about a murder-for-hire plot did not check out.

• Tipp City Det. Sgt. Mike Morgan, the lead investigator, then took the stand. Jurors watched Flynn’s first voluntary interviews after the shooting. In one he said he heard two shots; in a later interview he said he did not remember how many and told Morgan, “We are a normal married couple who love each other.” Morgan was still on the stand when court stopped. Court adjourned at about 3:09 p.m.

The trial resumes Monday, September 28, at 8:45 a.m., with Morgan still testifying and more of the recorded interviews still to be played.

Editor’s Note: for more in-depth information and reporting, please read our articles from BJ Bethel, the Tippecanoe Gazette reporter who is present every day in the courtroom for gavel-to-gavel coverage.