KAREN: THE RETRIAL

Episode S2-E7: "The Defense Strikes Back"
Law&Crime | Wondery • September 8, 2025
Host: Kristin Thorne

Episode Overview

This episode covers a pivotal phase in the retrial of Karen Read, accused of killing Boston Police Officer John O’Keefe with her SUV. Now, after the Commonwealth (prosecution) has presented its case, the defense team takes the reins. Their objective: dismantle the prosecution’s timeline, attack the investigation’s credibility, plant reasonable doubt, and promote alternative theories about O’Keefe’s death. Hosted by reporter Kristin Thorne, the episode features real courtroom testimony, expert analysis, and on-the-ground observations, immersing listeners in the drama, strategy, and stakes of this high-profile case.

Key Discussion Points & Insights

1. Defense Attempts Dismissal Before Presenting Case

• Alan Jackson, lead defense attorney, moves for an immediate acquittal, arguing the prosecutors have “no evidence” to support their theory.
  • “No reasonable jury could find Karen Reid guilty. This case never should have been brought in the first place. This was a vindictive prosecution...” — Alan Jackson (00:47)
• Prosecution's Response:
  • Prosecutor Hank Brennan highlights text messages, voicemails, and Karen Read’s own conduct as evidence.
    • “Any reasonable person could find that her conduct that night created a plain and strong likelihood of death.” — Hank Brennan (01:17)
• Judge Kanone swiftly denies the defense motion, and the defense is instructed to begin its case (02:21).

2. Digital Forensics and the Timeline Dispute

• Defense’s first witness, forensic expert Matthew De Sogra, challenges the prosecution’s timeline centered on a “lock event” on O’Keefe’s phone and Reed’s SUV movement.
  • He explains discrepancies in syncing electronic device clocks. (04:00)
    • “The phone, Mr. O' Keeffe’s phone, and the vehicle, Ms. Reed’s vehicle, they’re separate clocks, and it’s very unlikely that they're going to be aligned perfectly in time.” — Matthew De Sogra (04:00)
• Prosecution’s original expert (Burgess) revised his report during the retrial to introduce a “window” of possible overlap.
• De Sogra claims the “phone lock” mostly occurred after the vehicle had completed its motion, potentially supporting the defense theory that O’Keefe was alive after the car backed up (05:58).
  • Jackson distills the argument:
    • “Garbage in, garbage out. Basic scientific postulate.” — Alan Jackson (05:26)
• Critical Question: Can jurors grasp and care about this technical battle, or does it get lost in the weeds?
  • “I'm not sure that they will dive in quite that deep.” — Kathryn Loftus (07:10)

3. Bias and Investigation Integrity: Proctor’s Texts

• Defense calls Jonathan Diamandis, childhood friend of lead investigator Mike Proctor, to read out group chat texts allegedly revealing Proctor’s mocking and bias against Karen Read.
  • “We're gonna pin it on the girl. We’re going to make sure that there are some serious charges. She’s effed.” — read by David Yannetti, quoting Proctor (09:28)
• Prosecution counters that only Proctor himself can provide true context. Why hasn’t the defense called Proctor directly?
  • “They are trying to gain the advantage of putting information in front of the jury that has no context.” — Hank Brennan (12:26)
• Attorneys debate whether this creates a “boogeyman” effect with Proctor being alluded to but not actually present (13:36).

4. A Hostile Defense Witness: Officer Kelly Dever

• Officer Dever is called to support an alternative narrative about what happened in the garage with Reed’s SUV. Once on the stand, she repudiates her prior statements, suggesting she had a “false memory,” and alleges pressure from the defense.
  • “You threatened to charge me with perjury during our phone call prior to the first trial if I didn’t lie on the stand. Right now, I'm telling you I did not see anything factually.” — Officer Kelly Dever (16:21)
• The courtroom exchanges between Dever and Jackson become combative, with Dever referencing FBI involvement and emphatically denying being coached (16:42–18:27).
• Commentary observes Dever was neither helpful to the defense nor prosecution, and came off as combative and unreliable (20:06).
  • “She didn’t come off likable, she didn’t come off cooperative... She was a bad witness all around.” — Kathryn Loftus (17:14, 20:06)

5. Alternate Cause of Death: The “Dog Bite” Theory

• The defense’s medical expert, Dr. Marie Russell, argues some wounds on O’Keefe’s right arm are more consistent with a dog attack than a car accident, directly contradicting prosecution claims.
  • “In my mind I went through other possible things or causes of wounds on an arm and then I figured out why these other potential causes did not fit this case.” — Dr. Russell (23:25)
  • “Those wounds were inflicted as the result of a dog attack.” — Dr. Russell (29:38)
• Brennan, on cross-examination, emphasizes that Dr. Russell has never testified about dog bites as an expert in any other court before this case (25:08).
  • “You learned a little bit of information about it and it piqued your interest, didn’t it?” — Hank Brennan (25:41)
• A heated side dispute arises when Brennan mentions lack of dog DNA on the sweatshirt, with the defense objecting and even requesting a mistrial (27:02–27:48).

6. Eyewitness Testimony: Contradictory Accounts of Key Physical Evidence

a. Taillight Damage

• Officer Nicholas Barrows testifies that when he saw Karen Reed's car, the taillight had partial—not catastrophic—damage, unlike later photos supporting the prosecution’s timeline.
  • “It was not completely damaged... a piece was missing. Maybe the size of a dollar bill.” — Officer Barrows (30:40–30:54)
• Brennan attacks his credibility, noting the lack of detail in his original report and suggesting his recollection was influenced by social media and the defense’s outreach (32:55).
  • “Would you agree it’s had some effect on your memory?” — Hank Brennan (33:36)
  • “I know what I saw and that wasn’t it.” — Officer Barrows (33:42)

b. The Plow Driver

• Brian "Lucky" Loughran, a local contractor, says he plowed past the scene three times between 2:45 a.m. and 6:15 a.m. and saw neither O’Keefe's body nor evidence of distress.
  • “I could see all the way to the front door. I saw nothing.” — Lucky Loughran (35:48)
  • “They have never parked a vehicle in front of their house.” — regarding a Ford Edge at the scene (36:35)
• On cross, his timeline and consistency are challenged. Dashcam footage questions whether he could have visually confirmed the absence of a body (38:10).

Notable Quotes & Memorable Moments (with Timestamps)

- [00:47] Alan Jackson (Defense):

“No reasonable jury could find Karen Reid guilty. This case never should have been brought in the first place. This was a vindictive prosecution...”

- [01:17] Hank Brennan (Prosecution):

“Any reasonable person could find that her conduct that night created a plain and strong likelihood of death.”

- [04:00] Matthew De Sogra (Accident Reconstructionist):

“The phone, Mr. O' Keeffe’s phone, and the vehicle, Ms. Reed’s vehicle, they’re separate clocks, and it’s very unlikely that they're going to be aligned perfectly in time.”

- [05:26] Alan Jackson:

“Garbage in, garbage out. Basic scientific postulate.”

- [09:28] David Yannetti (on Proctor’s texts):

“We're gonna pin it on the girl. We’re going to make sure that there are some serious charges. She’s effed.”

- [13:36] Matt Timpanik:

“He’s just kind of this almost like Voldemort, this individual who you only hear about but you never actually really see until it’s too late.”

- [16:21] Officer Kelly Dever:

“You threatened to charge me with perjury during our phone call prior to the first trial if I didn’t lie on the stand. Right now, I'm telling you I did not see anything factually.”

- [20:06] Kathryn Loftus:

“She didn’t come off likable, she didn’t come off cooperative... She was a bad witness all around.”

- [23:25] Dr. Marie Russell:

“In my mind I went through other possible things or causes of wounds on an arm and then I figured out why these other potential causes did not fit this case.”

- [25:41] Hank Brennan (to Russell):

“You learned a little bit of information about it and it piqued your interest, didn’t it?”

- [29:38] Dr. Russell (conclusion):

“Those wounds were inflicted as the result of a dog attack.”

- [30:40] Officer Barrows:

“It was not completely damaged... a piece was missing. Maybe the size of a dollar bill.”

- [33:42] Officer Barrows (steadfast):

“I know what I saw and that wasn’t it.”

- [35:48] Brian “Lucky” Loughran:

“I could see all the way to the front door. I saw nothing.”

Important Segment Timestamps

| Timestamp | Segment/Topic | |-----------|-----------------------------------------------------------| | 00:47 | Defense motion to dismiss; prosecution response | | 04:00 | Digital forensics explained; witness De Sogra | | 06:55 | Attorney commentary on clarity of technical testimony | | 07:59 | Bias in investigation—Proctor’s texts | | 14:28 | Hostile defense witness: Officer Kelly Dever | | 21:22 | “Dog bite” theory: Dr. Marie Russell’s testimony | | 30:29 | Officer Barrows on taillight evidence | | 35:17 | Brian “Lucky” Loughran: plow driver testimony | | 39:23 | Defense strategy explained by Will Corman |

Analysis: Defense Strategy & The Stakes

• The defense’s “shotgun approach” attacks the prosecution’s evidence from every possible angle: forensic analysis, eyewitness credibility, investigatory bias, physical evidence inconsistencies, and alternate explanations for O’Keefe’s injuries.
  • “There are so many different components to the awful investigation… the defense had no choice but to sort of employ the shotgun blast approach.” — Will Corman (39:23)
• The episode underscores the complexity and high-tension atmosphere both in the courtroom and within the broader public narrative, with careers, reputations, and the very concept of justice on the line.

Coming Up

• The defense isn’t finished: more witnesses are expected, including key forensic experts (ARCA), with speculation building about whether Karen Read herself will take the stand.
  • “The decision whether or not to testify belongs to one person… and that’s the client, the defendant.” — Will Corman (40:35)

Tone & Language

The episode maintains a serious, investigative tone, matching the gravity of the trial and the charged emotions surrounding the case. The language is accessible yet detailed, with expert commentary routinely breaking down legal and forensic complexities for listeners.

In sum:
“The Defense Strikes Back” marks a turning point in the high-stakes retrial of Karen Read, spotlighting the defense’s relentless effort to craft reasonable doubt and unspool the prosecution’s narrative—one contradictory witness, piece of physical evidence, and alternative theory at a time. The episode is a legal chess match, rich with strategy, tension, and undercurrents of public scrutiny that color both courtroom and airwaves.