True Crime Obsessed – Episode 448: "The Murder of Hadass Winnick" (from "I'm Related to a Killer")

Air date: August 21, 2025
Hosts: Patrick Hines & Jillian Pensavalle

Overview

This gripping, non-comedic bonus episode of True Crime Obsessed launches the new series "I'm Related to a Killer," exploring true crime stories through the voices of murderers’ family members. This opening episode centers around the horrifying case of Jesse Winnick, who murdered his mother, Hadass Winnick, as recounted by his sister, Amy. The hosts approach the brutal case with gravity, empathy, and piercing perspective, emphasizing the systematic failures that left Amy and her mother helpless for years.

Main Discussion & Key Insights

1. Series Introduction and Case Overview

• The new series uniquely centers on stories told by relatives of murderers, providing a rarely heard perspective (01:13).
• The episode covers Jesse Winnick's vicious murder of his mother, Hadass, and the subsequent trauma faced by Amy, his sister (01:36).

2. The Immediate Aftermath and Amy’s Perspective

• Amy describes the night of the murder: working a shift, receiving frantic calls from her mother and brother, and then Jesse telling her flatly on the phone:

  "I just killed mom. Don’t come home." (05:09)

• Amy’s disbelief and shock, given Jesse’s long history of threats, triggers the frantic and apologetic 911 call (05:12-05:27).
• 22-year-old Amy arrives to find her mother murdered, marking the obliteration of her family as she knew it.

3. Family History and Cycles of Abuse

• Explores Hadass and Sherman Winnick’s marriage, Sherman's alcoholism and abuse, and their eventual separation (10:55, 11:09).
• Amy reveals, "By the time I was conceived, they were separated. So I never lived with my father. I never saw their marriage in person." (09:03)
• Family therapist Angela Mutonda describes every family as a "mini subculture," influencing how trauma and abuse are internalized (09:44).

4. Jesse’s Escalating Violence & Abuse

• Jesse’s abusive, controlling, and violent behavior began at an early age, escalating at home and at school, leading to his expulsion (15:53).
• Amy describes her brother:

  "The only times I ever can remember my brother being kind or loving or warm or caring were times when he wanted something from me." (15:10)

• He physically abused both Amy and Hadass, severely worsening after their mother’s injury left her wheelchair-bound (19:52-20:05).
• At 15, Jesse begins sexually abusing Amy, coercing her in deeply traumatizing ways (21:16):

  "He blackmailed me into inserting objects inside of myself in front of him. ... That had lasting effect on me." (21:16)

5. Lack of Institutional Help and Systemic Failure

• The hosts emphasize how almost no support was available for Amy’s family, highlighting overwhelming systemic failures (16:12-16:45).
• Police responses were limited to arresting Jesse for a night and then returning him home; mental healthcare failed to engage with him productively (25:04).

  "My mom called the police many times... They would arrest, they would detain him for a few hours, maybe a night, and then they would return him back home. That would happen for years." (25:04)

• Family bonds and cycles of violence kept Hadass attempting to fix and protect her son, even as his threats grew more explicit (29:04).

6. The Murder: Events and Aftermath

• On September 25, 2007, after escalating tension and trivial argument, Jesse stabbed Hadass to death in the kitchen (35:16, 37:54).
• Amy’s devastating discovery:

  "I initially saw at first was her hand outstretched and the phone just outside of her reach. And then I saw that the knife that Jesse had used to kill her was still in her neck." (35:43)

• Jesse calmly showered, changed clothes, stole his mother's car, met a friend, and attempted to flee – caught just miles away hours later (36:42).

7. Legal Proceedings and Continued Violence

• Jesse’s trial and sentencing were delayed for years as he manipulated the legal process by going off his medication, firing lawyers, and rendering himself unfit to stand trial (39:43).

  "He would start taking medication for one of his mental illnesses and then abruptly go off the medication right before the trial was supposed to start. Then he could be deemed mentally unfit to stand trial and the whole thing would be delayed again." (39:43)

• Eventually pleads no contest and is sentenced to 15 years to life, but his violence continues in prison, attacking both inmates and officers (44:56).

8. Amy’s Ongoing Trauma and Systemic Brokenness

• Jesse earns a parole hearing after only nine years. Amy attends and is threatened by her brother in front of the parole board, including him reciting her address and making throat-slitting gestures (47:07, 49:02):

  "He then recited a recent address of mine and said he could have friends visit me and take care of me and my children." (49:02)

• Prison officials, however, refuse to charge Jesse for these threats, citing "it's not a big enough threat" (50:07).
• Another plot is uncovered through a letter Jesse sends to another inmate, attempting to frame Amy and threaten her further, but DA Matt Allen prosecutes and Jesse receives an additional 36 years (51:04–52:16).

9. Amy’s Resilience and Advocacy

• Amy publicly testifies about her abuse, loss, and ongoing fear for the first time, while Jesse attempts to talk over her in court (52:38, 53:09):

  "She's not even safe from him when he's in prison. ... If he wants her dead, he can probably make that happen." (53:02–53:04)

• Amy chooses not to be consumed by hate, instead vowing to fight for better victim advocacy and systemic change (54:32–54:39):

  "I just want to change the way systems receive victims." (54:39)

• The episode ends with Amy reflecting on her love for her mother and the enduring impact of her loss (54:56):

  "I haven't heard her voice for 17 years. What a joyous person she was." (55:10)

Notable Quotes & Moments

• On Amy's Loss:

  "Her whole family is gone." — Patrick (36:11)

• Cycle of Abuse:

  "That is a cycle that I would see eventually carry over into my brother and my mom's relationship." — Amy (11:15)

• Systemic Failure:

  "There is such little help for families dealing with this." — Patrick (16:12)

• Jesse’s Violence in Prison:

  "I've stabbed over 90 people since getting here." — Jesse (47:07)

• Amy’s Determination:

  "I don't hate him. I'm angry. Like, I'll never forgive him. She's angry at her brother. She's angry at the system." — Jillian (54:10)

Important Timestamps

• 01:13 – Series introduction; premise of "I'm Related to a Killer"
• 04:28–05:09 – Amy receives call from Jesse admitting to murder
• 11:09–11:26 – Details on the abuse from their father carrying over into Jesse and Hadass’s relationship
• 15:10 – Amy describes her brother’s manipulative "kindness"
• 19:52 – Hadass's injury and heightening of Jesse's abuse
• 21:16 – Amy describes being sexually abused by her brother
• 25:04–25:23 – Police repeatedly return Jesse home, highlighting systemic helplessness
• 35:43–36:01 – Amy’s account of discovering her mother’s body
• 39:43 – Jesse’s courtroom manipulation and delay tactics
• 49:02 – Jesse threatens Amy during parole hearing, listing her address
• 51:04–52:16 – DA Matt Allen charges Jesse with further crimes after his death threats
• 54:39 – Amy’s mission to change how the system treats victims
• 55:10 – Amy remembers her mother’s joy and laments her absence

Themes and Tone

The episode maintains a somber, respectful, and empathetic tone while occasionally using the hosts’ signature informality for relief. By centering Amy’s firsthand perspective, the show avoids sensationalism and highlights the long-term consequences of family violence, the inadequacy of mental health and justice systems, and the resilience of survivors seeking change.

Summary prepared for listeners seeking a comprehensive, structured understanding of this episode’s content and emotional impact.