Dark Downeast: The Murder of Craig "Cooley" Jackman (Vermont)

Release Date: October 23, 2025

Host: Kylie Lowe

Episode Overview

This Dark Downeast episode, hosted by Kylie Lowe, explores the decades-old unsolved murder of Craig “Cooley” Jackman in Essex Junction, Vermont. The narrative delves into Craig’s sudden disappearance in 1981, the long quest of his family for answers, the tangled investigation that followed, and a justice system that left more questions than closure. Through meticulous research, interviews, and courtroom accounts, the episode honors Craig’s legacy while scrutinizing trust, betrayal, and systemic failure.

Key Discussion Points & Insights

1. The Disappearance of a Vermont Teen (02:03)

• On January 26, 1981, 16-year-old Craig Jackman vanished after declining a friend's invitation to go bowling. His mother, Carolyn, last saw him just before she left for a short errand; she returned to find him gone.
• Craig left with little money and none of his essential medications, which alarmed his family after he failed to return home. Flyers were distributed, newsletters contacted, and even psychics consulted in the desperate search.

Quote:
"She planned to do it again on her own birthday, January 1st. If Craig didn’t try to make contact with her on either date, she said, she’d know he was really gone."
— Kylie Lowe (07:56)

2. The Discovery of Remains & Autopsy Findings (08:59)

• In November 1985, Craig's skeletal remains were discovered by a hunter in the St. Albans woods, along with his clothing and wallet.
• Dental records confirmed Craig's identity; the autopsy indicated at least four head wounds from a blunt object, possibly an axe — his death was ruled a homicide.

Quote:
"The autopsy showed that Craig suffered at least four wounds to his head, and he was hit once in the jaw and twice in the back. His wounds were consistent with a blunt object, possibly an axe."
— Kylie Lowe (09:21)

3. Shifting Stories, Suspects & Motives (10:30)

• Detective Sergeant Leo Blais identified a recurring rumor centered on a stolen $300 check, cashed by Craig on behalf of Brian Wimble and Timothy Cruz.
• Brian and Timothy, both with criminal records, became key suspects. Both accused each other in separate statements, each attempting to minimize their own involvement.

Competing Accounts

• Brian Wimble’s Story: Claimed Timothy Cruz orchestrated the killing in an act of revenge for being allegedly (incorrectly) blamed for the check theft.
• Timothy Cruz’s Story: Accused Brian of plotting the murder out of fear Craig would expose him as the real thief.

Investigation Steps

• Police used an undercover tactic, sending a letter (purportedly from Brian) to Timothy, prompting Timothy to talk.
• Both suspects gave conflicting accounts but agreed that Craig was lured into the woods under the pretense of retrieving hidden marijuana.

Quote:
"Brian said that the stolen check was the whole reason why Craig was dead, but Brian insisted he wasn’t the one who wanted Craig gone."
— Kylie Lowe (15:11)

Quote:
"Timothy told police in his own interviews that it was Brian who wanted to do away with Craig because he was afraid of Craig telling police about the stolen check."
— Kylie Lowe (16:49)

4. Legal Proceedings: Pleas, Trials, and Tragedy (22:20)

• Both suspects were arrested and charged with first-degree murder.
• Cruz accepted a plea deal for second-degree murder, agreeing to testify against Wimble. He was sentenced to 15–30 years and expressed an emotional apology to Craig’s family.

Quote:
"He addressed Craig’s family, telling them he was sorry that Craig’s murder, ‘had to happen.’ He also said that if he could trade his life to get Craig’s life back, he’d do it."
— Kylie Lowe (26:19)

• Wimble’s trial was delayed and contentious. Despite emotional testimony and cross-examinations, the case boiled down to two mutually exclusive accounts.
• The judge refused to include lesser charges (like second-degree murder), so the jury could only convict on first-degree murder or acquit. After 11 hours of deliberation, Wimble was acquitted.

Quote:
"Brian Wimble. Not guilty. The jury acquitted him of first degree murder. Jury members commented in media reports at the time that if lesser charges were available... things may have played out differently."
— Kylie Lowe (36:41)

Quote (Carolyn, Craig’s mother):
"You know you did it, Brian. You know you killed him. You have to live with yourself."
— (38:01)

5. Aftermath and Ongoing Fallout (38:06)

• Both men continued lives marked by crime post-trial. Brian Wimble was later convicted of sexual assault against a minor. Timothy Cruz reoffended, including an accessory to murder conviction in 2004.
• The justice system’s shortcomings allowed these men to harm others after Craig’s murder.

6. Legacy: Family Grief, Advocacy, and Intergenerational Trauma (43:34)

• Craig’s mother and sister became advocates for victims’ families, fighting for policy changes and support.
• Suzanne (Craig's sister) co-founded the Boulder County Hospice Program for families of murder victims and served as a police victim advocate until her own death.
• Kylie interviews Suzanne’s daughter, Tiffany, reflecting on the family’s trauma and resilience.

Quote (Tiffany):
"The trauma is passed down, the sad and the hurt is passed down, but also being a survivor, the strength, the taking the good with the bad... my uncle was a victim. But the rest of us, we can choose to let it define us or do something about it."
— (47:16)

Notable Quotes & Memorable Moments

• On the difficulty of finding a missing child:
  “It was easier to find a missing car than it was to find a missing child, pointing to the fact that at the time, there was no national clearinghouse for missing persons.”
  — Kylie Lowe (07:45)

• Judge Mehade’s courtroom logic, as criticized by Suzanne:
  “A person has been violated and hacked to death, an innocent family destroyed by a maniac who is still walking the streets… because a trusted judge... made a decision that was too intellectual for lay people to understand.”
  — Suzanne’s letter, read by Kylie Lowe (44:01)

• Betrayal and deception:
  “When Craig was the best man at his friend’s wedding, the bride was Brian Wimble’s sister. Craig was named the Godfather to their child, Brian’s nephew. It’s an incomprehensible betrayal...”
  — Kylie Lowe (45:13)

Important Segment Timestamps

• Craig’s disappearance and initial search efforts: 02:03 – 08:59
• Discovery of remains & autopsy: 08:59 – 11:51
• Rumors and police focus shifts on suspects: 11:51 – 18:00
• Legal wrangling: Arrests, deals, and trial twists: 22:20 – 36:41
• Acquittal and family’s heartbreak: 36:41 – 38:06
• Aftermath: Later crimes, family advocacy, and legacy: 38:06 – 48:01
• Tiffany on trauma and resilience: 47:16

Tone and Language

Kylie Lowe’s tone is methodical, respectful, and empathetic. She centers the victims and their families, avoiding sensationalism and providing space for their voices. She highlights systemic flaws but remains heart-centered, honoring the memory of Craig and the advocacy born from his loss.

Conclusion & Reflection

This episode is a powerful, emotional journey through grief, betrayal, and injustice. It examines the enduring impact of a single crime—not just on one family, but also on an entire community and its justice system. Despite a lack of definitive closure, the advocacy and resilience shown by Craig Jackman’s family ensure his story lives on, serving as a beacon for other families still searching for answers.