The Alabama Murders - Part 5: Cruel and Unusual

with Linda Smith, Lee Hedgepeth, Joel Zivitt, Robert Grass

Published October 23, 2025
View Show Notes

About This Episode

Malcolm Gladwell examines the botched 2022 execution attempt of Kenny Smith in Alabama, situating it within the broader history and practice of lethal injection. Through interviews with Smith's mother, his longtime lawyer, a medical expert, and courtroom and press excerpts, the episode details Alabama's lethal injection protocol, previous failed executions, and the political response that extended the time window for executions. The story raises questions about what constitutes "cruel and unusual" punishment and how a method designed to appear humane can mask severe suffering and systemic failure.

Topics Covered

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Quick Takeaways

  • Alabama's lethal injection protocol, designed to appear humane and clinical, has led to multiple botched executions marked by prolonged attempts to place IV lines and extreme pain.
  • Kenny Smith, sentenced to death after a judge overrode a jury's recommendation of life without parole, endured hours of invasive needle sticks and a failed central line procedure during his aborted 2022 execution.
  • Medical experts highlight that finding veins in terrified, chronically imprisoned people is technically difficult, especially when the staff are not highly trained anesthesiologists.
  • Autopsy findings in a prior case, Joe Nathan James, revealed extensive IV attempts and a cut-down procedure that were inconsistent with Alabama's written execution protocol.
  • Following Smith's failed execution, Alabama's governor ordered a review that ultimately expanded the time window for executions rather than limiting or changing the method.
  • Attorney General Steve Marshall publicly framed complaints about the execution process as mere objections to "prodding and poking" with a small IV needle and criticized defense lawyers and inmates for delaying tactics.
  • Kenny Smith's lawyer, Robert Grass, describes Smith as a deeply changed, religious man who became a force for good in prison and with whom he developed a genuine friendship over nearly two decades.
  • The episode underscores a "moral failure cascade," in which a supposedly more humane method of execution, shielded from full public view, enables systemic cruelty and psychological harm.

Podcast Notes

Introduction: Pressure for a More "Humane" Execution Method

Perceived need to replace electrocution and lethal gas

Speaker describes pressure to find a method that looks more humane than electrocution and gas[2:57]
States were seeking an execution method that could be seen as less overtly brutal than older technologies like the electric chair and lethal gas chambers

Experience of officials tasked with executions

Official recounts having to tell the prisoner's family the execution was peaceful[3:19]
After the execution of John (John Parker from prior episode), the speaker returns to the hotel where family and supporters have been praying
They tell the family, "John's gone, it was peaceful, he didn't appear to suffer," highlighting the narrative presented to loved ones

Mechanism of lethal injection as described by an expert

Statement that lethal injection kills by burning the lungs while the prisoner is paralyzed[3:31]
The speaker says, "This is how lethal injection actually kills you. It kills you by burning your lungs up. And you're also paralyzed, so you can't complain that this is happening," emphasizing hidden internal suffering

Framing Kenny Smith's Case and the November 17, 2022 "Travesty"

Steve Marshall's press conference introduction

Attorney General Steve Marshall calls a press conference about capital punishment in Alabama[4:07]
He thanks the audience for coming and notes it is early December 2022 in Montgomery, Alabama
Marshall describes what happened on November 17 as a travesty, but disputes the reasons given by death penalty opponents[4:19]
He claims that many death penalty opponents and death row sympathizers would have the public believe it was a travesty for other reasons than those he endorses

Malcolm Gladwell situates the episode within the series

Gladwell introduces himself and the series "The Alabama Murders" on the Elizabeth Sennett case[4:35]
He states this is episode five, titled "Cruel and Unusual," focused on Kenny Smith and what was done to him in the name of justice

Kenny Smith's Background, Arrest, and Death Sentence

Personal background of Kenny Smith

Kenny Smith at the time of Elizabeth Sennett's murder[4:55]
He was 22 years old, had a girlfriend and two young children, and worked in a factory
Physically, he was described as slight, skinny, with dark hair and thick, moon-shaped eyebrows
He drank and used drugs a lot but was described as always smiling

Linda Smith's recollections of Kenny before his arrest

Linda Smith describes Kenny as a "happy drunk"[5:30]
She recalls Kenny and his son Michael coming over often, with Kenny grinning while high and drinking, and Michael sitting in a car seat in the back
Reporter Lee Hedgepeth introduces Linda and frames his coverage[5:30]
Lee Hedgepeth notes he has covered the Kenny Smith case and knows the family well, setting up his questions to Linda

Events around the time of the murder and Kenny's distress

Kenny's behavior the night of the attack[6:04]
On the evening after the attack on Elizabeth Sennett, Kenny's best friend came over and they went out to buy beer
Kenny's hand was swollen and wrapped in a bandage; he repeatedly said, "I messed up, I messed up" but would not explain why
Kenny's visits to his mother before his arrest[6:24]
Linda says he came over during that time and seemed distant, as though he wanted to tell her something but never did

Linda Smith learns of Kenny's implication in the crime

Phone call from Kenny as police arrive[6:53]
Kenny called Linda, asked if she could come pick up Michael, and mentioned that the police were at his house
Linda initially assumed it was about pot or drugs; she told him she was washing her hair but would come shortly
Scene at Kenny's house when Linda arrives[7:28]
When she drove up, there were about ten police cars out front, indicating the seriousness of the situation

Kenny Smith's conviction and sentencing

Parallel to John Parker's case[7:37]
Kenny, like his friend John Parker, was charged with murder, convicted, and his jury recommended life without parole by a vote of 11 to 1
Judicial override to impose death[7:59]
Despite the jury's recommendation, the judge overrode the decision and sentenced Kenny to death
Decades on death row before the 2022 execution date[7:59]
Kenny was sent to Holman Prison and spent decades there, appealing his sentence and delaying the execution until November 17, 2022

Alabama's Lethal Injection Protocol and the Problem of IV Access

Attorney General Marshall's dismissal of complaints about IV insertion

Marshall criticizes sympathetic media coverage of Kenny Smith's execution attempt[8:24]
He notes coverage has been sympathetic and has even led some to advocate abolishing the death penalty
Marshall characterizes Smith's objections as complaints about "prodding and poking"[8:39]
He frames the basis for criticism as a "cold-blooded convicted killer" complaining about "the prodding and poking of a small IV line," rhetorically ending with "Really?"

Overview of Alabama's written execution protocol

Nature and disclosure of the protocol[9:07]
Alabama has a detailed, 41-page protocol specifying how executions are carried out, including timelines, last meals, allowed possessions, and witness arrangements
The protocol was originally not public but was forced into disclosure during a death penalty court case
Execution team composition and preparation[9:40]
The execution team consists of about a dozen people and has a captain
They are supposed to conduct a walkthrough in the week leading up to the execution as a kind of "batting practice" to perfect the procedure

Origins and appearance of lethal injection

Ronald Reagan's suggestion and the idea of "putting to sleep"[10:01]
Gladwell recalls Ronald Reagan asking why executions couldn't be done the same way horses are put down-"put to sleep"-to create a clean and professional appearance
Medical expert Joel Zivitt on the "bloodless" appearance of lethal injection[10:47]
Zivitt notes that lethal injection seems effective and sinister because, to observers, it is bloodless and looks like someone closing their eyes and dying peacefully
He contrasts this with earlier methods that were far more graphic, arguing that lethal injection solved the "witness experience" problem by being outwardly peaceful
He adds that the use of medical terminology and even physicians lent an impression of legitimacy

Specific protocol language on IV and central line

Protocol clause about IV team entering the chamber[11:51]
Section B, Part 1, Clause A states the IV team will be escorted into the execution chamber to start the IV and apply heart monitor leads
Fallback to central line if veins are difficult[12:04]
If the condemned inmate's veins make venous access difficult or problematic, qualified medical personnel may perform a central line procedure as set forth in an appendix
Explanation of central line procedure[12:04]
A central line involves inserting a long, thin, flexible tube into a large vein such as the jugular, subclavian, or femoral vein
The plan in theory is to try the arm first and, if that fails, move to a big vein using a central line

Why IV insertion is hard in execution settings

Zivitt outlines conditions that make vein access difficult[13:17]
He explains that placing an IV requires technical skill and some cooperation from the person, as needle sticks hurt
In young, fit, relaxed, and well-hydrated individuals, success is high, but in dehydrated, terrified prisoners who have been in poor conditions for decades, it becomes more difficult
Lack of expert medical staff in executions[13:52]
Zivitt notes that anesthesiologists in good standing do not participate in executions, so the people inserting IVs are not the same as in hospitals
He suggests those doing the procedures may themselves be nervous and less skilled, further complicating IV placement
Alabama's secrecy about the execution team[14:22]
Alabama will not reveal exactly who is on the execution team, their training, or experience
Gladwell points out that because of the medical oath to do no harm, it is unlikely the team is staffed by physicians, reinforcing Zivitt's argument about non-expert personnel

Witness perspective and timing as clues to problems

Hidden IV procedures in Alabama compared to other states[15:10]
In some states, IV placement occurs in full view of witnesses, but in Alabama it is done before witnesses are brought in, making the process opaque
Delays as signs of difficulty in the chamber[15:20]
Executions are scheduled to begin at 6 p.m.; witnesses are sequestered elsewhere, and if they have not been brought in by 7, 7:30, or 9 p.m., people start to suspect problems inserting IVs

Prior Botched Executions in Alabama: Joe Nathan James and Alan Miller

Case of Joe Nathan James

Execution delays and state's assurances[16:11]
In summer 2022, Alabama executed Joe Nathan James; the process ran late, but the state later insisted everything went according to plan
Zivitt's second autopsy and findings[16:20]
Suspicious of the official account, Zivitt obtained James's body and worked with a pathologist in Alabama to perform a second autopsy
They found evidence of multiple IV attempts with bruising up and down both arms, indicating needles had repeatedly entered and left veins, causing bleeding under the skin
They also found evidence of a "cut down"-an incision made with a knife to open the skin and reveal a vein-which was not provided for in the execution protocol
Blood along the edges of the cut down indicated it was performed while James was alive and bleeding
Reconstructed experience of James's execution[17:44]
Zivitt imagines James strapped down, not cooperative, being repeatedly poked with needles and eventually having his forearm cut open to reach a vein

Case of Alan Miller

Death warrant timing constraints and failure[18:15]
Under Alabama law at the time, once a date was set, the execution had to occur by midnight at the Holman Prison facility in Atmore
For Alan Miller, officials started at 6 p.m. with a six-hour window but ran out of time and abandoned the attempt, requiring a new death date to be set
"Then came Kenny Smith" as next in the sequence[18:51]
Gladwell notes that after James and Miller, the next condemned person in line was Kenny Smith, linking his case to this cluster of failed executions

Portrait of Kenny Smith Through His Lawyer's Eyes

Introduction of lawyer Robert Grass

Grass's professional background and role[22:23]
Grass is a litigator at a prestigious corporate law firm in New York City who represents pharmaceutical companies and does pro bono death penalty work
He began representing Kenny Smith in 2005 and had been with him the longest among his lawyers

Grass's impressions of Kenny's character in prison

Kenny's transformation and religious turn[21:49]
Grass says Kenny "got religion" both figuratively and literally in prison and became a "force for good" there
He emphasizes that his description may sound trite or clichéd, but that Kenny truly embodied this change by the time Grass knew him
Friendship between lawyer and client[23:07]
Grass says he and Kenny developed a friendship and that he would have liked to know Kenny under different circumstances
He notes they grew up in very different circumstances, yet he still felt a bond, unlike with some other death row clients he had represented
Grass describes Kenny as a decent man, incredibly gracious, and leading as productive a life as possible in the prison environment

Logistics of representing Kenny over many years

Travel demands on Grass[23:22]
Holman Prison is in southern Alabama; Grass would travel from New York to Atlanta, then to Mobile, rent a car, and drive about an hour to Atmore, repeating this for nearly two decades

Legal Maneuvers and the November 2022 Death Warrant

Death warrant and new challenge based on prior botched executions

Smith receives a death warrant setting November 17, 2022 as execution date[25:03]
In fall 2022, Smith is given a death warrant with a set execution date, following many years of appeals
Use of Joe Nathan James and Alan Miller cases to argue cruelty[25:12]
Grass and his team argue that Alabama's practice of lethal injection, as demonstrated in the cases of James and Miller, constitutes cruel and unusual punishment
They file a lawsuit making this claim, but the case is dismissed in the lower court
Appeal to the 11th Circuit Court of Appeals[25:42]
Grass appeals to the 11th Circuit in Atlanta; arguments are heard on November 16, the day before the scheduled execution
After the hearing, Grass travels directly to Atmore to visit Kenny at Holman Prison as they await the appellate decision

Evening of November 17: Conflicting rulings and running out the clock

Initial reports of preparation for execution[26:20]
Around 8 p.m., Grass, in a nearby hotel, hears that guards have taken Kenny from his cell and are preparing him for execution even though the appeal is unresolved
Temporary reprieve from the 11th Circuit[26:28]
Shortly afterwards, Grass learns that the 11th Circuit has ruled in Kenny's favor, halting the execution
Alabama's appeal to the U.S. Supreme Court[26:34]
The state of Alabama immediately appeals to the U.S. Supreme Court, while the death warrant still specifies an execution must occur before midnight
Grass watches the clock, hoping to reach midnight without a decision so the warrant will expire
Supreme Court ruling against Kenny and movement of witnesses[27:05]
At about 10:15 p.m., Grass receives a call from the Supreme Court's emergency clerk, sometimes called the "death clerk," who tells him the Court has ruled for Alabama
A reporter at Holman emails Grass that witnesses are being moved to the death chamber, indicating the execution is proceeding

Inside the Failed Execution of Kenny Smith

Kenny's account of being strapped down and left waiting

Initial period on the gurney with no clear information[28:00]
Kenny is taken from his cell, strapped to a gurney, and believes his execution is imminent, but for a time nothing happens
He asks corrections officers what is going on; they tell him they don't know

Attempts to place IVs and central line without explanation

Unidentified IV team and repeated needle sticks[28:17]
Kenny describes three members of an IV team, none identified to him, and other unidentified people in the chamber
They jab him with needles trying to find a vein but cannot successfully place an IV
Attempted central line under the collarbone[28:47]
They attempt a central line procedure by trying to stick a needle under his collarbone to reach a central vein, again without explaining what they are doing
Kenny notes that one IV team member returns in surgical garb, and they put a surgical gown over him

Detailed report of the invasive procedures on Kenny

Description of chest injection and Kenny's terror[29:17]
In a report commissioned by his legal team, Kenny recalls a clear plastic sheet over his chest with an open center, and a man injecting a yellow liquid into his chest after unbuttoning his shirt
The man says, "you will feel something cool" as he slides a long needle into Kenny's chest and moves it around while inserted
Kenny says he "lost all composure," describing the situation as surreal and feeling terrified he was being injected with something that would render him unable to communicate, which he believed would violate a court order
Fear of being silenced before final words[30:17]
Kenny was panicked that he would be unable to deliver his final words to his family and the victim's family, especially after hearing about what had happened in a previous execution
Large-gauge needle attempts under the collarbone and physical struggle[30:35]
After stepping back, members of the team return; one behind his shoulder holds a large-gauge needle with a large cylinder, prompting Kenny to "freak out" and demand that someone call his lawyer
Deputy Warden Woods puts his hands on both sides of Kenny's head, telling him "this is for your own good" and pulls his head to the side
Kenny recalls searing pain as he is injected under his collarbone, saying "it took my breath away" and that he gasped and bucked up off the table trying to escape
He believes the man tried approximately five times to get the large needle into a vein under his collarbone

Physical aftermath for Kenny after hours on the gurney

Loss of basic physical functioning[31:28]
After three and a half to four hours strapped to the gurney, Kenny was unable to stand, walk, unbutton his shirt, change clothes, or perform basic movements without assistance
End of the attempt and return to infirmary[31:55]
Near midnight, Kenny could not stand and requested a wheelchair, which was refused
He sat outside the chamber until guards picked him up by the arms and carried him to the infirmary

Reflections on the Execution Team and Moral Conflict

Imagining the perspective of the execution team

Gladwell's speculation about the team's emotional state[31:57]
Gladwell imagines the team assuming the procedure would be clean and professional, only to realize they were over their heads and could not complete it
He suggests they were trapped in the execution chamber until midnight, facing their own sense of shame and self-loathing
Use of Graham Parker lyrics to capture the mood[32:27]
Gladwell quotes lyrics about a doctor fumbling during a procedure, being "all rubber gloves and no head," and wishing he were dead, drawing a parallel to the execution team's possible feelings after the failed execution

Political and Policy Response: Governor Ivey and Attorney General Marshall

Governor Kay Ivey's pause and review

Immediate aftermath decision[35:36]
Kenny Smith's failed execution occurred on a Thursday; by the following Monday, Governor Kay Ivey paused all pending executions and ordered a top-to-bottom review of Alabama's capital punishment protocol

Steve Marshall's December press conference and blame on timing

Marshall's claim that defense lawyers game the six-hour window[36:05]
Marshall argues that, given a six-hour window from 6 p.m. to midnight, defense lawyers simply try to "push the clock back as far as possible" to delay executions
Marshall blames inmates for resisting IVs[36:41]
He says inmates themselves share responsibility by resisting efforts to insert IV lines, which he argues makes the process more difficult

Discussion of legislative options and extended execution window

Reporter question about alternative methods or longer windows[36:53]
A reporter asks whether the legislature could add another method of execution or extend the time window to 48 or 72 hours
Marshall indicates review will consider window length[37:03]
Marshall notes Alabama technically has a 24-hour period, but in practice only six hours, and states this is one of the things the review would examine
Outcome of the "top-to-bottom" review[37:35]
Gladwell reports that the review resulted in a new rule allowing guards at Holman Prison until the following morning to complete the execution, effectively adding about six hours
He interprets this as providing more time for invasive attempts at IV access and central lines, while staff cope with rising shame and revulsion at the task

Return to Marshall's "prodding and poking" remark

Gladwell contrasts Marshall's framing with Kenny's experience[38:05]
Gladwell repeats Marshall's line about complaints over "prodding and poking of a small IV line" and juxtaposes it with the hours-long ordeal Kenny endured
Concept of a "moral failure cascade"[38:39]
Gladwell says that as the "moral failure cascade" gains momentum, indifference turns to cruelty, describing the trajectory of the system's response

Unresolved Questions and Next Steps: Psychological Impact and Future Episodes

Kenny's situation after the failed execution

Alive but traumatized back in his cell[38:49]
Gladwell notes that after the failed attempt, Kenny was back in his cell, still alive, raising the question of what happens next
Legal and ethical question of retrying execution[39:08]
Gladwell poses the question of whether, if the state botches an attempt, that should disqualify them from trying again

Need for psychological assessment and involvement of Kate Porterfield

Lawyers seek expert assessment of Kenny's condition[39:12]
Robert Grass and the legal team decide they need an assessment of Kenny's condition after the failed execution before proceeding further
They look for someone who understands what it might be like to be strapped to a gurney for hours while being stabbed with needles
Introduction of psychologist Kate Porterfield[39:29]
They contact Kate Porterfield, who will assess Kenny; she will be a focus of the coming episode

Teasers of emotional and family perspectives

Porterfield on Kenny's unmanageable human moments after the attempt[39:52]
Porterfield says one of the people on the execution team told Kenny, "it's over, and I'll be praying for you," and that such moments became unmanageable for him afterwards
Linda Smith's reflection on Kenny's jealousy and responsibilities[40:22]
Linda says that after Kenny was born she thinks he was jealous and suspected she was doing things, while she emphasizes she had a child to raise
Gladwell's observation of Kenny starting from a place of love[40:26]
Porterfield remarks that watching Kenny, after something so horrible, "only start from a place of love" made her pause and think, as she had never seen that before

Credits and Production Details

Production team and roles

List of producers and contributors[40:38]
Gladwell names producers Lucy Sullivan, Ben-Nadav Haffrey, and Nina Byrd Lawrence, with additional reporting by Ben-Nadav Haffrey and Lee Hedgesbeth
He credits editor Karen Shikurji, fact-checker Kate Furby, executive producer Jacob Smith, and notes engineering by Nina Byrd Lawrence
He mentions production support from Luke Lamond, original scoring by Luis Guerra with Paul Brainerd and Jimmy Bott, and sound design and additional music by Jake Gorski
Host sign-off[41:02]
Malcolm Gladwell signs off by name at the end of the credits

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Systems designed to appear humane can conceal severe harm when implementation details are opaque and poorly executed, especially when the stakes involve life and death.

Reflection Questions:

  • Where in my own organization or community do reassuring appearances potentially mask painful or harmful realities for the people most affected?
  • How might I build in mechanisms for transparency and independent scrutiny when the processes I oversee have serious consequences for others?
  • What is one concrete step I can take this month to make a high-stakes process I'm involved in more visible and accountable to outsiders?
2

Technical procedures become ethically fraught when those performing them are undertrained, anonymous, and shielded from normal professional standards and accountability.

Reflection Questions:

  • In what situations do I rely on people to carry out complex tasks without giving them the training, support, or ethical framework they really need?
  • How could clarifying roles, qualifications, and lines of responsibility improve both outcomes and moral clarity in my current work?
  • What is one process I'm part of where I could insist on minimum standards of competence and oversight before allowing it to continue as usual?
3

Legal and bureaucratic actors often frame systemic failures as problems of timing or cooperation, deflecting attention from deeper structural flaws and human suffering.

Reflection Questions:

  • When I hear leaders explain failures primarily in terms of scheduling or non-cooperation, how can I probe for deeper structural issues that might be the real cause?
  • How might I change my own language so that I acknowledge human impacts rather than reducing problems to technical or procedural glitches?
  • What current challenge in my life or organization would look different if I focused less on blaming individuals and more on examining the design of the system itself?
4

Long-term, committed advocacy-like a lawyer visiting a client for years-can humanize people that systems have written off and can surface injustices that would otherwise remain hidden.

Reflection Questions:

  • Who in my orbit is being treated as a case number or problem to manage, and how could I invest time to understand their story more fully?
  • How might committing to show up consistently for one difficult person or cause over the next year change my perspective on justice and responsibility?
  • What is one relationship or issue I can choose to stay with over the long term, even when there is no quick or obvious payoff?
5

When institutions are allowed to hide the most difficult parts of their work from public view, moral desensitization can escalate into what feels normal, even as cruelty increases.

Reflection Questions:

  • What practices in my field or community are routinely kept out of sight, and what might I discover if I insisted on seeing them up close?
  • How would my decisions change if I or the public had to witness the full consequences of policies I support or processes I manage?
  • What is one hidden or uncomfortable area I can deliberately bring into the open so that I, and others, have to confront its moral implications?

Episode Summary - Notes by Alex

The Alabama Murders - Part 5: Cruel and Unusual
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