True Crime Garage: Kierra Coles /// Part 1

Release Date: December 2, 2025
Hosts: Nic & The Captain
Main Theme:
The disappearance of Kierra Coles, a 26-year-old pregnant USPS worker from Chicago, missing since October 2018. Nic and the Captain break down the timeline, family dynamics, questionable behavior from close associates, challenges with public information, and the unsolved nature of the case.

Episode Overview

The first part of this two-part series delves deep into Kierra Coles' life, the circumstances of her disappearance, her strong family ties, suspicious clues uncovered by her relatives, challenges the investigation faced (including misleading surveillance and complicated relationships), and growing suspicions around her boyfriend. The hosts analyze the case through both investigative details and the emotions of those left behind.

1. Kierra Coles: Background and Family

• Kierra Coles

  • USPS letter carrier, recently promoted to full-time, living independently in the Chatham neighborhood of Chicago.
  • Described as ambitious, outgoing, stylish (“hair done, nails done, dressed very nicely”), and family-oriented.
  • Known as “Boss Lady Coles.”
  • Only notable health issue: asthma, managed with an inhaler.

• Family

  • Close-knit, loving, protective—mother (Karen Phillips) and father (Joseph Coles) heavily involved after her disappearance.
  • Family nickname reveals Kierra’s strong personality and presence.

"She was already excited about becoming a mother. That's all my child ever wanted to be, a mom."
— Karen Phillips (09:10)

2. Timeline & Initial Disappearance

Key Dates:

• October 1–2, 2018

  • Kierra takes 2 days off work, believed related to a prenatal appointment.
  • Last spoken to by her mom (7:00 PM, Oct 2) while at a WIC grocery store (talked about eating healthy and buying baby items).
  • "Last known in-person sighting" by family occurs Oct 2.

• October 3, 2018

  • Kierra's mother (Karen) can’t reach her; calls go straight to voicemail.
  • No Snapchat or social updates—a red flag.
  • Noted Kierra had called in sick again that morning; calling in sick at USPS requires a detailed, unique process.

• October 4, 2018

  • Karen visits Kierra’s apartment and finds the TV on, no response, and car parked down the block (not in her usual spot).
  • Kierra’s boyfriend, Josh Simmons, claims he doesn’t have a key—though Kierra told her mom he did.
  • Police arrive, force entry: apartment in perfect order, no sign of struggle, groceries from last shopping trip put away.

Notable Segment:

"She always answers the phone and she's always Snapchatting, and none of this is happening."
— Nic (12:27)

Vehicle Clues:

• Car found down the street, not in usual spot; groceries brought in previously.
• In car: Kierra’s packed lunch, purse, coat, phone (under jacket), mail cart in trunk.
• Family unable to access phone due to password protection.

"Her keys and her wallet are in the house… So, where is she at? Did she take off on foot somewhere?"
— The Captain (17:58)

3. Immediate Search and Law Enforcement Response

• Actions Taken:

  • Karen and Joseph distribute flyers, go door to door, call hospitals, check with friends—no news.
  • Missing person report filed; both CPD and USPS inspectors investigate.
  • Family starts to suspect foul play early, given Kierra’s lifestyle and excitement about the baby.

• Boyfriend's Behavior:

  • Josh Simmons (also USPS) is reportedly detached:
    • Claims no key to the apartment (despite what Kierra told her mom).
    • Not actively participating in searches or distributing flyers.
    • Stories about last contact with Kierra are inconsistent.

"He hadn’t seen or talked to Kierra all day... He doesn’t seem too worried."
— Nic (15:59)

4. Surveillance Video & Timeline Complications

• Discovery:

  • Surveillance video provided by a neighbor, timestamped October 3, 11:54 AM, appears to show Kierra (in USPS uniform) walking past her own car, crosses the street, exits frame; widely circulated in media.

• New Revelation:

  • Karen reviews the video repeatedly and insists “that’s not my daughter,” citing subtle physical differences and her maternal instincts.
  • Police later confirm the woman in the video is a different female postal worker from the block, not Kierra.
  • But, police ask Karen to keep this information quiet for over two years, using the video as a tool to generate leads and bring people in for questioning—even though it misled the public timeline.

Notable Quotes:

“It’s a mother thing. You just know your child. That’s not her walk.”
— Karen Phillips (37:03)

"You have this tool that you've put out to the people that is snaring individuals coming into you and saying, 'Oh, I knew this young woman.'"
— Nic (39:16)

5. Complicating Factors & Theories

• Suspicion on the Boyfriend (Josh):

  • Dated for six years, but after Kierra goes missing, it’s uncovered he had another long-term partner (also at USPS) named Kiara—with whom he has children.
  • Both Kierra and the other Kiara apparently knew about each other; unclear if the situation was fully amicable or tolerated.

• Police Perspective:

  • Josh gives “varying accounts” and later refuses further questioning (“lawyers up,” ceases cooperation).
  • Moves out of state after the disappearance.
  • Never publicly named a suspect but widely viewed as acting suspiciously.

"Old Red Flag Josh works for the postal service. He would know the ins and outs.”
— The Captain (48:57)

“After his initial interview, Josh at some point lawyers up and reportedly has never talked to police since he gained counsel.”
— Nic (58:15)

• Call-In Procedure:

  • USPS call-in process is complex and only known by employees; whoever called in sick for Kierra could’ve been someone close, with knowledge of her employee information.

• Other Rumors:

  • Baseless speculation about family members (e.g., stepdad Dan Perkins) circulates with no supporting evidence.

6. Law Enforcement Investigation — Communication Challenges

• Information Release:

  • Chicago PD is characteristically tight-lipped, citing the need to preserve investigation integrity.
  • Limited information creates tension between generating public tips and sharing (potentially misleading) material.

• Family Action:

  • Joseph (father) leaves Wisconsin to stay and search in Chicago.
  • Karen (mother) continuously pushes for the case, never wavering in public.
  • Josh’s inaction and contradictory statements widen the rift with Kierra’s family.

Notable Quote:

"You dated my daughter for six years… now my daughter is pregnant and missing and you do nothing."
— Karen Phillips (61:06)

7. Notable Theories & Emotional Reflections

• Potential Foul Play:

  • Hosts discuss that violence against pregnant women is, disturbingly, a leading cause of death.
  • The timeline of her disappearance is murky due to the misleading surveillance video and the unclear call-in process.

• Hosts’ Perspectives:

  • Strong emotional statements admiring Karen’s relentless efforts (“I love Karen in this case. Every interview… she’s not going to give up. And I’m glad this case is getting a little more attention.” — The Captain [44:18]).
  • Frustration at law enforcement’s information strategy, but understanding the complexity (“What do you release to the public and what do you hold back...” — The Captain [54:08]).
  • Dark humor and banter are woven in, lightening the otherwise heavy investigation.

8. Timestamps for Key Segments

• [03:17] – Listener letter prompts the case, Kierra’s background introduced
• [09:42] – Pregnancy and family reactions
• [13:26] – Timeline: last conversations, failed call attempts, initial worry builds
• [16:32] – Mom, boyfriend, and police search apartment
• [17:58] – Discovery in Kierra’s car and clues about her disappearance
• [22:48] – USPS call-in system complexity and its investigative significance
• [32:49] – Surveillance video’s emergence; public is misled
• [36:20] – Karen disputes video is of Kierra and police confirm, but ask her to remain silent
• [47:57] – Only someone with USPS experience could convincingly call in sick for Kierra
• [55:25] – Kierra’s boyfriend’s secret relationship and his unreliable statements
• [58:49] – Josh ceases cooperating and moves away
• [61:06] – Karen’s anguish and confrontation with Josh’s lack of involvement

9. Memorable Quotes

"It's a mother thing. You just know your child. That's not her walk." — Karen Phillips [37:03]

"No sign of a struggle, no sign of robbery. Kiera's car is there, but it's not in her normal parking spot." — The Captain [17:58]

"If you have a suspect pool... you can limit that pool of suspects to somebody that would have knowledge of that system. Meaning either they're a postal worker themselves or they had witnessed a postal worker do this multiple times." — Nic [48:57]

"This lady is brilliant... I'm glad this case is getting a little more attention." — The Captain [44:18]

10. Conclusion & Preview

Nic and the Captain conclude Part 1 emphasizing the unexplained clues, the suspicious actions of Kierra’s boyfriend, and the family’s ongoing fight for answers. They tease further discussion, including what more recent revelations and theories have arisen in the years since her disappearance, for Part 2.

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Next Episode:
Kierra Coles /// Part 2 — A deeper investigation into new evidence, further reflections from Kierra’s family, and examining what’s needed for justice and closure.

“Be good, be kind and don’t litter.”
— The Captain [62:31]