Small Town Murder: "Murder of the Queen – Madisonville, Kentucky"

Date: December 11, 2025
Hosts: James Pietragallo & Jimmie Whisman

Overview

In this episode, James and Jimmie take listeners to Madisonville, Kentucky—self-dubbed “The Best Town on Earth”—to dive into the brutal and bizarre murder of beloved local businesswoman Anna May “Ann” Branson, known as the “Dairy Queen.” Through their signature mix of exhaustive research and sharp comedy, the hosts peel back the deceptively plain layers of small-town life to uncover a dark family betrayal involving greed, gambling, and a savage murder that shocked 20+ years of small-town tranquility.

Key Discussion Points

1. Madisonville: Small Town Personality

• Geography and Demographics:
  • Western Kentucky, population of ~19,500, median age 36.5, mostly working-class.
  • Mottos: “Best Town on Earth” and “Where Small Town Warmth Meets Infinite Possibilities.” (07:00)
• Economy & Culture:
  • Historically a coal and tobacco hub, now faded.
  • Not much to do: “If you want a bar, the only options are Tumbleweed or Applebee’s.” (11:35, James)
  • “One of the most corrupt places I’ve ever been.”—One-star town review, which the hosts hilariously dissect. (11:44)
• Crime Rate:
  • Very low murder rate—no murders in 20 years before Ann’s case.

2. Victim Profile: The Iconic Dairy Queen

• Anna May Branson (Ann): Born 1917, local legend, Depression survivor, self-made Dairy Queen franchise owner (since 1950s), real estate mogul, family benefactress, flamboyant, adored.
  • “There’s always money in the Dairy Queen,” quips Jimmie. (33:46)
  • Known for fur coats with the animal’s head still attached, high heels into her 80s, signature purple-ink ledger, and extreme generosity.
  • She had no children, was the glue and piggybank for her sprawling extended family, but was also known to be a shrewd businesswoman who tracked every debt to the penny.

3. The Murder

• Discovery & Crime Scene (Jan 13, 2003):
  • Dr. Bob (her fiancé) and Ann’s brother Earl find her facedown in the basement—initially thought to be a fall, quickly revealed as a “slaughterhouse.” (45:04-46:41)
  • Detective: "Her face was unrecognizable from blunt force that caved her skull..." (51:43; Mary Kinney Branson, victim’s niece and author)
  • 97 stab wounds, severe blunt force trauma; described as an act of extreme rage.
    • “This person was so enraged they just kept stabbing and stabbing.” (53:47, James; quoting medical examiner)
  • No weapon found; no forced entry; rings and cash untouched; suggests personal, not robbery.

4. Initial Investigation & Suspects

• Family and friends: Dr. Bob, brother Earl, and cancer-stricken sister Grace—a parade of unlikely and mostly quickly ruled-out suspects, each explored for both alibi and comic effect.
• Town landlord/handyman Wayne Shelton and unstable tenant “Robert Prince/Joseph K.”: Both investigated due to opportunity and motive (rent/eviction), but each clears via alibi or polygraph.
  • “He would actually call her in the middle of the night and say that he had ghosts up in his attic. And would she please get rid of the ghosts?” (72:17, James)
• Town and family worry the killer might be a random maniac due to lack of leads.

5. Break in the Case: The Nephew

• Russell Winstead: Ann’s nephew, race-car driver turned mining-equipment salesman, deacon, Little League coach, all-American family man…with a devastating gambling addiction and $97,000 debt to Ann, all tracked in her purple-inked ledger. (88:49-90:49)
  • “He visited casinos in the previous year of 2002…236 times…lost hundreds of thousands of dollars.” (97:59-98:11, James)
  • Russell had written a bad $1,200 check as a token payment before immediately gambling and losing the latest $9,700 loan from Ann.
• Timeline & Confrontation:
  • Placed with Ann near time of murder; wife Tammy’s alibi falls apart under questioning—“He told me to say 7:25.” (119:14, Tammy’s confession)
  • Polygraph results: “100% probability of deception on the question about stabbing, 99% about hitting her on the head.” (127:24)
• Search & Discovery:
  • Burner phones for secret casino affair; custom hunting knife consistent with murder weapon under his mattress; cash/valuables untouched at the crime scene.
  • Russell flees to Costa Rica (prompted by convenient U.S. laws and high-stakes casinos; Costa Rica offers no extradition for potential death penalty cases).

6. The International Manhunt and Capture

• Flight and Support:
  • Russell supported by his father Earl (Ann’s brother), who wires him stolen inheritance money via a middleman.
    • “She is still paying for this asshole to gamble now”—James (142:31)
  • Sting operation catches Earl, who receives probation and house arrest. (144:04)
• America’s Most Wanted tip: American tourist recognizes Russell at Costa Rica casino from a rerun, leading to his arrest in 2005: “How did you find me?” asks an exhausted Russell. (151:09)

7. Trial & Aftermath

• Prosecution: Built around circumstantial evidence, financial motive, polygraphs, witness contradictions, and Russell’s flight as “consciousness of guilt.”
• Defense: Points to lack of forensic evidence, mismatched timeline (some expert debate on exact time of death), and attempts to cast doubt on ex-wife’s credibility.
• Intriguing Twist: Accused murderer and cellmate Fred Roulette confesses—later revealed to be a ruse/paid confession by Russell (157:52). Fred returns to recant after learning he could face the death penalty.
• Verdict: After 6 hours, the jury convicts Russell Winstead: Life without parole for 25 years plus 20 for robbery (concurrent after appeal).
• Aftermath:
  • Russell is currently serving his sentence, eligible in 2032.
  • Ann's legacy is still felt in Madisonville; Dr. Bob visited her grave weekly until his death.
  • Book “Murder in Mayberry” by Mary Kinney Branson covers the case in detail.

Notable Quotes & Memorable Moments

• On Madisonville’s quirks:
  “Their law enforcement set people up. The task force and all. They are all awful.” (12:57, James reading local review)
• On Ann’s style:
  “She wears mink coats with the head still on. I have a picture...from the 60s...I saw eyes.” (34:26, James)
• On small-town generosity:
  “She’s the family’s bank...She’s always very well put together—high heels even into her 80s.” (35:10, James)
• On the murder’s brutality:
  “97 stab wounds! Do that 97 times, and your arm is sore—like you can’t...” (53:02, James)
• On Russell’s gambling addiction:
  “236 trips to the casino in one year—that’s every two days!” (98:11, James)
• Confronting Tammy’s alibi:
  “He told me to say 7:25.” (119:14, Tammy’s confession)
• Russell’s doomed flight:
  “She is still paying for this asshole to gamble now—on another continent.” (142:31, James)
• Russell’s arrest in Costa Rica:
  “How did you find me?” (151:09, Russell)
• On defense arguments:
  “The prosecution wants you to convict based on debt and suspicion. That’s not how justice works in America.” (161:09, Defense Attorney)
• On Ann’s generosity and impact:
  “Every Christmas morning I would walk over to her house. We just looked forward to seeing her at Christmas time. I miss her smile perhaps more than anything.” (153:42, Tom Branson [nephew])

Important Timestamps

• 05:42 – Introduction to Madisonville, Kentucky (“Best Town on Earth”)
• 24:41 – Ann’s early life & rise to business owner
• 33:38 – Ann’s personality and reputation (“money in the Dairy Queen”)
• 40:48 – Ann’s new romance with Dr. Bob, even in her 80s
• 45:04 – Discovery of murder; crime scene description
• 53:02 – Medical examiner details 97 stab wounds, skull fragmentation
• 72:17 – “Attic ghosts” tenant as suspect
• 88:32 – Ledger found, showing Russell’s staggering debt
• 97:59 – Russell’s 236 casino trips in one year
• 119:14 – Tammy reveals her husband asked her to lie
• 127:24 – Polygraph reveals near-100% probability of deception
• 142:31 – Earl wiring inherited money to fugitive Russell in Costa Rica
• 151:09 – Russell arrested, “How did you find me?”
• 157:52 – Fake confession by fellow inmate Fred Roulette
• 174:36 – Verdict: guilty on all charges, life sentence
• 180:06 – Dr. Bob’s devotion & Ann’s legacy

Tone & Style

The hosts blend deep research and respect for the victim with rolling, riff-heavy comedy. They skewer everything from town slogans (“infinite possibilities!”), to the absurdity of small-town drama and police mishaps, to the killer’s delusional double life, keeping the story fast-paced, darkly hilarious, and yet genuinely empathetic to its tragic heart.

Final Thoughts

The murder of Ann Branson shattered Madisonville’s self-image as “The Best Town on Earth.” Amid a festival of bad debts, family secrets, compulsive gambling, and some truly Kentucky-specific quirks (like a church dinner followed by homicide), the episode unravels the sad unraveling of a family—reminding listeners that, in the words of Mary Kinney Branson, in Madisonville, “blood matters.”