Last Podcast On The Left: Episode 645

Ronald Gene Simmons Part I – A Difficult Man

Release Date: December 5, 2025
Hosts: Marcus Parks, Henry Zebrowski, Ben Kissel, Ed Larson

Episode Overview

This episode launches a two-part exploration of Ronald Gene Simmons, infamous for committing the deadliest single-family annihilation in American history. Known as a “difficult man,” Simmons was responsible for the 1987 Arkansas Christmas Massacre, murdering 14 members of his own family and several others. The hosts dive into his background, personality, pathologies, military career, and the toxic family dynamics that led up to his horrifying crimes.

Main Themes & Purpose

• Examination of Simmons as the archetype of a “difficult man” – controlling, entitled, mean-spirited, and utterly irredeemable.
• Dissection of Simmons’s background, from his childhood to military career, his obsessions, and the seeds of control and abuse that culminated in mass murder.
• Reflection on broader patterns in “family annihilator” cases, masculinity, American violence, and the enabling structures within both family and military contexts.
• Dark, irreverent humor mixed with researched true crime storytelling.

Key Discussion Points

1. Introducing Ronald Gene Simmons: The Ultimate Difficult Man

• (02:06) Marcus: “Ronald Jean Simmons, I'm going to say, is up there with one of the bigger pricks we've ever covered.”
• Christmas link: Simmons committed the massacre during the holidays, making his crime the highest body count of any holiday mass murder in America (03:54).

2. Simmons’ Crimes Summarized

• (04:56) Over one week in December 1987, Simmons—a former military man—murdered 14 family members, including his wife, children, and grandchildren. Among the victims: a grandchild from an incestuous relationship with his daughter.
• (05:58) After the familial murders, Simmons continued a shooting spree around town to “settle scores” with enemies: women who rejected him, coworkers, and businessmen.

3. Personality Profile: The Archetype of Toxic, Controlling Men

• Simmons was “sneered at by his siblings, despised by his family, shunned by his co workers, and ignored by the outside world” (Marcus, 09:28).
• The hosts compare Simmons’s personality to today’s online “know-it-all” toxic men:
  • Aggressively pedantic, hyper-controlling, spends all his time opining, profile pic in Oakleys, exposed as a sex criminal (Marcus, 10:48).
• Discussion of how the digital age amplifies such personalities, possibly fueling greater cases of violence due to loss of status and entitlement (12:10–12:36).

4. Sources and Reference Books

• Main source: Zero at the Bone by Bryce Marshall & Paul Williams. Described as classic ‘90s trashy true crime (13:04).

5. Childhood & Family Dynamics

• Born 1940 in Chicago; father died when Simmons was 3; mother quickly remarried another William.
• Simmons remembers his years (5–10) in Hector, Arkansas, as idyllic and becomes obsessed with returning—“He created a spectacular childhood that Ronald would chase for the rest of his life” (Henry, 20:11–20:28).
• Early signs of jealousy, defiance, and cruelty: Physically and emotionally tormented his younger brother, controlling and mean-spirited (22:32–24:05).

Notable Quote:

“If you crossed Ronald or if things didn't go his way, Ronnie Jean would throw fits, bellowing and stomping until everyone else just gave up and agreed with him.” – Henry (23:42)

6. Move to Adolescence & Early Adult Years

• Adolescence marked by more rebellion, control issues, and refusal to follow rules.
• Developed aversion to smoking—became “militant nonsmoker,” performatively gagging and coughing when others smoked (28:09).
  • “His attitude towards cigarettes was so ridiculous that it was described by his future brother in law as, quote, comically prudish.” – Henry (29:00)
• No religious conviction, but obsessive patriotism; identified more with America and military order than any faith (29:25–29:59).

7. Life in the Military

• Joined the Navy at 17; found a personal “religion” in strict hierarchy and bureaucracy.
• Proved adept at administrative work, but failed to make friends – drank alone, developed odd habits, continued controlling behavior.
• Married Becky, a “normal person who just got mixed up with a psychopath,” and began a largely abusive marriage soon after (34:55–35:03).
• Pattern: Each new posting (Guam, San Francisco, England, New Mexico) brought more control, more withdrawal, more abuse.

8. Early Family Life and Abuse

• Refused Becky a phone, controlled her mail, prohibited her from driving—carried out all measures to isolate and dominate his family (38:45–39:53).
• Obsessively cataloged family finances and goods, tracked every penny.
• Simmons’s obsession with his idyllic Arkansas childhood grew, all plans orbiting around returning and establishing a labor-force family on a self-sustaining farm (44:32–44:55).

9. Vietnam Era & Heightened Narcissism

• Volunteered for Air Force Office of Special Investigations (OSI) in Vietnam—not for combat, but to enforce rules as a “narc” on black market rings (45:35–46:51).
• Marcus: “His job was to make the lives of others harder. People who are in an already impossible situation.” (47:29)

10. Mortifying Family Situation

• While Simmons was on assignment, his family endured bleak isolation and near-poverty in trailers with little money or opportunity to escape (51:04–51:44).
• On returning to America: continued as an enforcer, collecting infractions and ruining lives, never liked nor feared—"just an annoyance you had to deal with" (52:47–53:14).
• Tightly controlling, increasingly obsessed with guns and the purity of his household and lineage; racist, paranoid, and apocalyptic in outlook (63:39–65:44).

11. Incest & Escalating Abuse

• By the late ‘70s, Simmons’s abuse extends to his daughter Sheila. Began taking naked photos of her, sexualizing, and eventually raping her, defending this as “the natural instincts of a father” (59:08, 70:00).
• Pattern of enforced pregnancy on Becky, even at risk of her life.

Notable Quotes:

“Ron became so obsessed with his daughter that when the family would take drives, Sheila would sit up front alone with him while his wife Becky and the other four children were forced to cram themselves in the back seat.” – Henry (60:19)
“He was signaling to his whole family that Sheila gets treated differently. And I have a sexual attraction towards Sheila. And you're all going to have to deal with it.” – Henry (60:05)

Memorable Moments and Quotes

• American Masculinity & Revenge:
  • “I'm going to destroy my own world because I can.” – Ben Kissel, riffing on the American fantasy of ultimate control (08:25)
• Incisive Characterization:
  • “He makes John List charming.” – Marcus, referencing another infamous family killer (09:00)
  • “He was obsessed with keeping lists, notes and records... so exacting that his wife and kids would hide their…” – Henry (62:22–44:55)
• On Military Bureaucracy:
  • “The army likes having those guys... The military always needs guys that nobody likes.” – Marcus (43:13)
• On Family Labor:
  • “Ronnie Jean had his kids perform concentration camp style labor. Although that's a bit of an overstatement.” – Henry (67:44)

Humor & Tone

• The hosts maintain irreverent, often dark humor about Simmons’s priggishness, the banality of evil, and their own personal experiences (e.g., comparing parental spankings, discussing gun nuts, and critiquing pop culture archetypes).
• Running jokes about “difficult men” and their affinity for rules, petty authority, and lording over others.

Important Timestamps

• Main Topic Begins: 03:33
• True Crime Sourcebooks Discussed: 13:03
• Simmons’s Childhood Details: 18:35–24:05
• Early Marriage & Militancy: 32:09–38:45
• Control of Family & Finances: 43:33–44:55
• Military Narcissism & OSI: 45:35–47:29
• Family Isolation & Poverty: 51:04–51:44
• Incestuous Abuse of Daughter: 59:08, escalates at 70:00
• Family Rebellion and the Coming Massacre: 68:55–72:08
• Episode Wrap-up & Next Week Preview: 72:08

Preview for Next Episode

The episode concludes with a preview that part two will bring the break between Simmons and his family to its horrific climax with the details of the Christmas Massacre.

TL;DR / Key Takeaways

• Ronald Gene Simmons embodied the most toxic traits of the “difficult man”—controlling, authoritarian, emotionally and sexually abusive, friendless, and determined to impose his warped order on the world.
• The seeds for his crimes were sown through decades of increasing isolation, misogyny, entitlement, and loathing—culminating in mass murder.
• The LPOTL team layers their deep research with gallows humor, offering pointed insights into the anatomy of family annihilators and the social structures that produce and protect them.
• The episode closes with a promise to continue the unraveling tragedy in part two.

Recommended Segment to Hear Simmons's Personality Deconstructed:

• 09:28–12:36 — The hosts break down the personality type, draw modern parallels, and lampoon the online “difficult men” archetype.

Notable Quote to Sum Up the Episode

“He is the archetype of the difficult Man... There is no redeemable quality.” – Henry & Ed (72:15–72:23)