Podcast Summary
Criminal – "The Test"
Original Air Date: February 6, 2026
Host: Phoebe Judge
Guest: Makeda Brotman (author, reporter)
Topic: The mysterious disappearance and murder of Mike Williams, unraveling a complex story of betrayal, obsession, and justice in Tallahassee, Florida.

Overview

In this gripping episode of Criminal, Phoebe Judge and author Makeda Brotman recount the dramatic story of Mike Williams’ disappearance in 2000, his mother Cheryl Williams' tireless quest for truth, and the ultimate revelation of a murderous conspiracy involving Mike’s best friend and his wife. The episode explores the themes of love, faith, betrayal, and the perseverance needed to solve a case that baffled authorities for years. The narrative delves into small-town dynamics, family bonds, and the complicated intersections of religious conviction and moral failings.

Key Discussion Points & Insights

Disappearance & Early Investigation

• Mike Williams’ Disappearance (01:08)

  • Mike, an experienced hunter, went missing on a solo duck hunting trip at Lake Seminole on his wedding anniversary.
  • Efforts by his wife Denise and friends to locate him were hampered by a storm, and only his car and later his boat were found.
  • Massive search efforts, including the use of helicopters, cadaver dogs, and underwater cameras, yielded no body (03:42).

• Alligator Theory Rejected (05:43 - 06:46)

  • Lake Seminole was known for its alligators, fueling speculation that Mike had been eaten.
  • Experts dismissed this, explaining that alligators do not feed in winter, and his gear was found unscathed (06:36).
  • Mike’s mother, Cheryl, publicly challenged the prevailing theories, convinced he was still alive or had met another fate (07:23).

Cheryl Williams’ Relentless Pursuit (07:47)

• Cheryl’s faith and drive propelled an independent investigation:
  • She organized flyer and billboard campaigns and engaged with missing persons networks.
  • Cheryl’s persistence put her at odds with Denise, who preferred to trust authorities’ conclusions (08:18).

Unraveling Relationships & Motives

• Insurance Payouts and New Relationships (08:47)

  • Denise received $1.8 million in life insurance benefits after Mike's presumptive death, facilitated by Brian Winchester’s father.
  • Denise and Brian (Mike’s best friend) soon became a couple, eventually marrying after both divorced their spouses (13:10–19:28).

• Background on Relationships (12:44-14:44)

  • The four main figures—Mike, Denise, Brian, and his wife Kathy—had deep ties going back to childhood in a tightly-knit Baptist community.
  • Hidden desires and secret affairs between Brian and Denise led to marital discontent.

• Religious Justification and "The Test" (15:24-16:56)

  • Brian and Denise rationalized their relationship as divinely ordained and concocted a "test" for Mike:
    • If Mike died in a staged hunting accident, it was a sign from God.
    • If he survived, they would interpret it as a warning to end the affair (16:56).

• The Murder Plot (16:32–18:03)

  • Brian took out a new $1 million insurance policy on Mike.
  • Brian and Denise planned the fatal duck hunting trip, with Brian to push Mike overboard.

Aftermath, Suspicion & Community Pressure

• The Aftermath (18:52–22:24)
  • As Denise and Brian moved forward with their relationship, local suspicions grew.
  • Journalist Jennifer Portman pursued the case annually, noting the suspicious insurance policies and the subsequent marriage of Denise and Brian (20:09).
  • Brian and Denise began communicating via covert hand signals, growing increasingly paranoid.

Break in the Case: Divorce, Threats, and Confession

• Relationship Breakdown and Arrest (24:10-29:21)
  • Denise eventually sought divorce. Brian responded with drinking and instability, culminating in a 2016 kidnapping attempt, which Denise reported.
  • Brian was arrested and faced serious charges. Prosecutors offered a deal: testimony about Mike’s disappearance in exchange for immunity (30:45–31:11).

The Full Story Revealed

• Brian’s Confession (31:11–35:17; 36:23 [quote], 37:36)
  • Brian explained he pushed Mike into the lake, expecting him to drown, but Mike survived by clinging to a stump.
  • In a panic, Brian retrieved a gun and shot Mike. He then concealed the body in a dog crate, staged alibis, and buried Mike near Tallahassee.
  • Police recovered Mike’s remains after a six-day search following Brian’s detailed directions.

“He was taking the waders and the jacket off, and he got those off and…he swam over one of those stumps and held onto it. And he was panicking and I was panicking...I ended up circling closer towards him. And as I passed by, I shot him.”
— Brian Winchester, courtroom confession (36:23)

Justice and Controversy

• Denise on Trial (35:17–40:09)
  • Brian received a 20-year sentence for kidnapping; Denise was charged with first-degree murder.
  • Denise was unexpressive during the trial, which was harshly judged by observers (37:36).

“There was absolute silence in the courtroom, and there was absolutely no expression from Denise at all. And this was held against her that she seemed to be so cold and stoical when learning these dreadful, traumatizing fact."
— Phoebe Judge (37:36)

• The prosecution relied entirely on Brian’s testimony; Denise’s murder conviction and life sentence were later overturned on appeal, citing no evidence she assisted in the actual murder. She was resentenced to 30 years (40:09).

"She did not assist or encourage Bryan at the time of the murder…her life sentence was overturned, and she was resentenced to 30 years."
— Makeda Brotman (40:09)

Cheryl Williams: The Relentless Mother

• Cheryl’s impact as the driving force in seeking justice is praised, with powerful courtroom statements and recognition from journalist Jennifer Portman.

“December 16, 2000. My life as I knew it changed forever. There is no how to find your missing child manual. I did what God told me to do.”
— Cheryl Williams (40:39)

“If not for Cheryl Williams, there’s no way that we would know where Mike Williams was or anything that ever happened to him.”
— Reporter Jennifer Portman (41:04)

Notable Quotes & Memorable Moments

• On the “test” philosophy:

  “If Mike drowned, that was God saying, Yes, it’s my will that you two should be together. But if he survived, that was God saying, No, I don’t want you to be together.”
  — Phoebe Judge (16:56)

• On Brian’s paranoia:

  “They developed this range of hand signals...holding bars, as if you were miming that you were in prison. And if either of them made one of these gestures, it meant they wanted to talk about the crime. They…leave their cell phones in the car…sometimes even take the batteries out.”
  — Phoebe Judge (21:23)

Timeline (Selected Key Timestamps)

• 01:08 – Introduction to Mike’s disappearance
• 03:42 – Search efforts and lack of evidence
• 05:43 – Alligator theory and its dismissal
• 07:23 – Cheryl’s refusal to believe Mike drowned
• 08:47 – Insurance issues and Denise/Brian relationship
• 12:44 – The foursome’s background and church community
• 16:32 – Plotting the murder and the “test”
• 18:52 – Aftermath and community suspicion
• 20:09 – Jennifer Portman investigates
• 24:10 – Denise and Brian’s relationship deteriorates, kidnapping incident
• 29:21 – Police offer Brian a deal to confess
• 31:11 – Brian describes the murder in detail
• 36:23 – Brian’s confession in court
• 37:36 – Reaction to Denise’s courtroom demeanor
• 40:09 – Denise’s conviction overturned, Cheryl’s statement

Conclusion

"The Test" delivers a haunting, meticulously reported story of a man’s disappearance, the obsessive devotion of a grieving mother, and a tragic love affair that led to murder. Through interviews and courtroom testimony, Phoebe Judge and Makeda Brotman uncover not only the facts but the complex human motivations that drive people to horrific decisions. Ultimately, it’s Cheryl Williams’ unwavering quest for answers that brings justice and closure—even at immense personal cost.

For further details on this story, read Makeda Brotman’s book "Guilty Sex, God and Murder in Tallahassee, Florida," or listen to this full episode of Criminal.