Last Podcast on the Left: Side Stories - Dig Me A Grave w/ Dick Harpootlian
Episode Date: November 26, 2025
Host: Ed Larson (with Henry Zebrowski in side stories, then Ed interviews Dick Harpootlian)
Guest: Dick Harpootlian, former South Carolina Senator, prosecutor, and defense attorney
Overview
This episode of Side Stories features Ed Larson interviewing South Carolina legal legend Dick Harpootlian about his new true crime book, Dig Me A Grave, centered on the prosecution of notorious serial killer Donald "Pee Wee" Gaskins. The episode weaves classic Last Podcast banter with a deep dive into Gaskins’s crimes, the ethics and mechanics of the death penalty, and Harpootlian’s unique career crossing both prosecution and defense in some of the South’s most infamous cases—including the recent Alex Murdoch trial.
Main Themes and Discussion Points
1. Casual Side Stories Banter and True Crime Roundup
Notable Moments:
- Henry and Ed riff on Zoomer culture, Thanksgiving laziness, and TV fridges (03:00–05:00).
- Discussion of current crime stories—Morgan Geyser (Slenderman stabber) escaping a halfway house with aid from a “victim advocate,” and skepticism about her release (06:53–09:10).
- Overlap with the side stories’ “curse”—news stories wrap up too soon for full coverage (10:15).
- Brief speculation and sardonic jokes about the incoming “Epstein files” and potential political fallout (10:26–12:08).
Quote:
- “The side stories curse. It was wrapped up already, at least.” — Henry (10:15)
2. Introduction to Dick Harpootlian and "Dig Me A Grave"
Transition: Ed takes over, setting up his nerves over interviewing a “prestigious” former Senator and defense attorney (15:00).
Background
- Harpootlian was the prosecutor on the Gaskins case, oversaw 15 death penalty prosecutions, and later became a noted defense attorney and South Carolina Senator.
- His book Dig Me A Grave chronicles the Gaskins case, Pee Wee's crimes, and reflections on justice, ethics, and capital punishment.
3. The Life and Crimes of Donald "Pee Wee" Gaskins
Key Discussion (15:39–51:00)
Gaskins's Kill Count and Modus Operandi
- Largest serial killer in South Carolina history, “convicted of murder number 14” (15:47).
- Chilling description of Pee Wee smuggling C4 into prison to kill another inmate on death row (16:32).
- “He arranged…to kill the perpetrator of that armed robbery…smuggled in a quarter of a pound of C4 explosive…blew the guy's head off.” — Harpootlian (15:47)
Tape-Recorded Confessions and Evidence
- Harpootlian shares that Gaskins recorded conversations arranging the prison murder, some of which he still possesses (16:58).
Escapes and Influence in Prison
- Gaskins was “the model inmate,” gained status in prison as "building man" with practical skills, enabling privileges and control (18:32).
- Multiple escapes as a youth and criminal, including bending courthouse window bars and writing "I was here, haha Peewee" in dew on a cop car (38:59–42:10).
Racially Motivated and Familial Victims
- Pee Wee was described as a "virulent racist," and some of the most heinous murders involved a pregnant woman and her mixed-race child (19:00).
- First known murders: his niece Janice Kirby and her friend, beaten to death and hidden in a septic tank (55:01–58:45).
Danger to Prosecutor’s Own Family
- Gaskins, before his execution, plotted from prison to have Harpootlian’s 4-year-old daughter kidnapped for leverage to escape (22:00).
- “He attempted to have my four year old daughter kidnapped and held hostage two weeks out to try to get me to get him brought up to the courthouse…” — Harpootlian (21:58)
Body Count Exaggerations
- Gaskins claimed over 100 murders in his autobiography, The Final Truth, but Harpootlian is skeptical: “He always wanted people to think that he was a big guy at 5 foot 2 and 110 pounds. He obviously had some issues about being the biggest, the best or whatever.” (44:33)
- Harpootlian's documentation pegs the number at 14 confirmed, with detailed confessions backed by forensic corroboration.
Associates and Manipulation
- Gaskins surrounded himself with social outcasts and was described as "charismatic"—able to persuade others to kill or aid escapes (55:10).
- Orchestrated "love stories" from prison, like with Suzanne "Long Legs" Owens, who escaped custody and remained on the run for years at his command (59:00–61:12).
Quotes:
- “He was a killing machine… cunning.” — Harpootlian (43:49)
- “This book is virtually 100% accurate.” — Harpootlian, holding up the original 500+ page confession transcript (61:53)
4. Capital Punishment—Ethics and Mechanisms
Switching Death Penalties: Electric Chair, Firing Squad, and Lethal Injection
(30:49–35:02)
- Harpootlian championed bringing back the firing squad as more humane than the electric chair:
- “When Gaskins was executed, his hair caught on fire, his eyes exploded…We're better than him.” (30:57)
- Describes current options in SC: “You can choose firing squad, lethal injection, or the electric chair.” (31:20)
- Firing squad mechanics: three shooters, all with live rounds, using .30-06 rifles with laser sights, and a target over the condemned's heart (32:28).
Never Watching an Execution
- Harpootlian refused to attend Gaskins's execution:
- “I’m better than Gaskins. I wasn't gonna go watch him die. He enjoyed watching people die. That's not what I … enjoy.” (36:35)
Personal Toll of Capital Cases
- Six weeks after Gaskins’s execution, Harpootlian quit as prosecutor from the trauma—acknowledging the emotional cost (37:51).
5. Murdoch Case and Legal Philosophy
(62:00–79:51)
The Murdoch Family and Alec Murdoch Trial
- Harpootlian’s history with the Murdochs: knew the family through multiple generations of South Carolina solicitors (64:03–66:29).
- Defended Paul Murdoch (Mallory Beach boat homicide), then, after Paul's death, Alec Murdoch in the murder of his wife and son.
- Argues Alec Murdoch may have been wrongfully convicted, presenting evidence gaps (no blood on Alec, odd timeline, conflicting forensics) and problematic conduct by the court clerk (70:07–75:57).
- “I don't think he killed Maggie and Paul… The download shows that, that Alec drove that vehicle to the house at Moselle, parked it…Maggie's phone is being thrown out on the side of the road while he's a half mile away cranking his car…” (70:11–75:52)
Defense Ethics and Public Judgment
- On defending guilty clients: “When you're a defense attorney, your duty is to represent your client…You don't fabricate evidence, you don't help…you make the system work.” (76:43–79:17)
- Relates the tradition back to John Adams defending British soldiers (Boston Massacre).
- On public criticism: “How can you represent that guilty son of a bitch? I hope you die of ass cancer.” (80:33, quoting hate mail)
Notable Quotes and Memorable Moments
On Gaskins’s charisma:
“He was sort of charismatic. And of course, the flotsam and jetsam of society gravitated around him.” — Harpootlian (55:10)
On the personal cost of prosecution:
“It was traumatic…six weeks later I quit.” — Harpootlian (37:51)
On the American justice system:
“It’s not about winning or losing. This isn’t the football game…The rule of law keeps all of us free.” — Harpootlian (78:19)
Key Timestamps
- 00:01–01:16: Ads/banter, skip content
- 03:00–05:03: Henry and Ed riff on holiday laziness/fridges
- 06:53–09:19: Morgan Geyser escape story/Splenderman context
- 10:26–12:08: Epstein files jokes/political jabs
- 15:00–15:39: Ed’s nerves introducing Dick Harpootlian
- 15:47–18:32: Pee Wee Gaskins C4 prison murder operation
- 21:58–23:26: Plot to kidnap Harpootlian’s daughter
- 30:49–35:02: Detailed description of firing squad, capital punishment ethics
- 36:35: Harpootlian refusing to watch Gaskins execution
- 44:33: Debunking Gaskins’s claims of 100 victims
- 55:01–58:45: Pee Wee’s first convicted murders (niece and friend)
- 61:53: The confessions transcript—foundation for the book
- 64:03–66:29: Harpootlian’s connection to the Murdoch family
- 70:07–75:52: Alec Murdoch’s case, evidence breakdown
- 76:43–79:17: Ethics of criminal defense
- 80:33: Harpootlian on hate mail and public backlash
- 81:29: Interview conclusion
Final Thoughts
This episode blends the dark humor and macabre levity of Last Podcast on the Left with a rare, in-depth look into the realities of prosecuting and defending the vilest criminals. Harpootlian is candid, measured, and surprisingly philosophical, sharing both astonishing true crime stories and nuanced takes on justice, ethics, and the flaws of the system. Dig Me A Grave is pitched throughout as an extremely thorough primary documentation of Pee Wee Gaskins—rife for anyone who loves true crime with firsthand access.
Ed’s closing summary:
“I really appreciate you coming in. Pick up the book Dig Me a Grave… You were amazing. I'd love to talk to you more again sometime about the Alex Murdoch case…” (81:26)