Podcast Summary: The Wayback with Ryan Sickler

Episode 113: Tim Dimemmo | Baltimore Junkyard Series #113

Date: February 26, 2026
Host: Ryan Sickler
Guest: Tim "Timmy" Dimemmo

Episode Overview

In this nostalgic and riotous episode of "The Wayback," Ryan Sickler returns to his Baltimore roots, recording with family and old friends at Shannon Patterson's Junkyard Auto Recycling. His guest is cousin/brother-in-arms, Tim Dimemmo, as they dive deep into the wild, rough-and-tumble tales of growing up in blue-collar Baltimore. Packed with stories of family dysfunction, resilience, misadventure, and laugh-out-loud memories, this conversation paints a vivid portrait of a tight-knit but chaotic Italian-American family navigating mental illness, poverty, and the unique cultural quirks of Baltimore’s east side.

Key Discussion Points and Insights

1. Family Origins and Early Chaos

• Background

  • Tim shares the history of his parents meeting and the early days in O’Donnell Heights, a mostly Black housing project where they were the only white family ([03:53]).
  • He describes a tumultuous home life—his mother left, taking one sister to Virginia and leaving Tim and siblings with their mentally ill father ([04:41]).

• Insanity and Survival

  • Tim and his brother were shaped by their father’s paranoia and mania—he was always training them to fight, convinced someone was out to get them:

    “We were raised in an environment that we thought somebody was always trying to get us. We were always training to fight. I mean, we were fighters.” —Tim ([08:03])

2. “Growing Up Assassins”

• Roughhousing as Way of Life

  • Regular visits meant hours of physical combat, wrestling, and kung fu practice, all orchestrated (and encouraged) by their father ([09:04]).
  • Ryan recalls how these visits left them exhausted (“You guys left our house... you guys were in the car napping hard.” —Ryan, [10:00]).

• Legendary Strength and Eccentricity

  • Tim’s dad’s Bruce Lee obsession led to him punching cinder blocks barefoot and performing one-finger push-ups in public ([10:06]).

  • “He can put his foot through a watermelon.” —Ryan ([10:41])

  • Memorable story of dad knocking a neighbor out cold with an unopened beer can, and the family camaraderie that followed ([10:46]).

3. Mental Illness, Courtroom Drama & Family Support

• Father’s Legal Troubles
  • A courtroom story where the judge addresses “Aunt Marguerite” for using “hun” in legal proceedings, and the chaos around their dad’s love songs to a hairdresser ([13:04]).

  • “First of all, you will not address me as ‘hun’ in a court of law. You will address me as ‘Your Honor’.” —Judge (paraphrased, [13:45])

4. The Baltimore Kid Experience

• City to County Culture Shock

  • Stories of Tim and Gary’s awe as city kids experiencing cows and horses for the first time when visiting Ryan in the county ([16:01]).

• Train Tracks Adventures

  • Tales of breaking into parked trains (“Olympic suits and socks for Christmas”), rolling under moving trains, and pelting cars and buses with snowballs from the overpass, gamifying the chaos ([17:06], [18:24]).

  • “We were doing it for fun all the time.” —Tim ([17:55])

5. Teenage Misadventure: Sister’s Party Debacle

• Epic Party Goof
  • Ryan recounts getting Tim dangerously high at his sister Jennifer’s birthday, causing him to collapse and nearly needing CPR ([22:15]).

  • “You got knocked the f*** out!” —Jennifer, channeling the movie "Friday" ([25:42])

  • 17 out of 19 girls at the party were tripping on acid, leading to chaos when Tim appeared with blood on his lip, ruining any chance of romantic success that night ([26:39]).

6. The Family’s “Come Up” — Rite Aid Lawsuit

• Class Action Hero

  • Aunt Marguerite and other Rite Aid employees are falsely accused of embezzlement, agree to take lie detectors, pass, and ultimately win a substantial class action lawsuit ([32:54]).

  • “She was the ringleader... said ‘you’re not going to call me a liar or a thief.’” —Tim ([33:56])

  • Family’s lifestyle improves: “It was party time for the whole family… she was buying for everybody, bro.” —Tim ([34:20])

• Moving Up (Sort of)

  • Despite the payout, the family only moves just across the city line:

    “‘We’re fucking millionaires, we’re out of the city!’ Y’all went right here, Rosedale.” —Ryan ([35:04])

7. More Family Hijinks & Generational Dynamics

• Carrying Caskets and Tables

  • The family, repeatedly forced into funeral pallbearer roles, naturally slips into “pallbearer formation” when clearing a picnic table, providing comic relief in darker times ([39:24]).

  • “We were always pallbearers…If you could get the leg-end, that was the light end.” —Ryan ([39:24])

• The Old Head Women Running Things

  • Discussion on the dominant matriarchs of the family holding things together, protecting reputations, and doling out support ([42:52]).
  • Stories of family secrets, inheritance, and uncovering treasures:

    “When I saw this, I thought about you right away…that was your dad’s, man.” —Tim (on finding Ryan’s dad’s Navy tool, [42:23])

Notable Quotes & Memorable Moments

• On the Family’s City Survival Instinct:

  “We were assassins. If Aunt Marguerite doesn’t get a hold of you guys — we were in prison.” —Tim ([12:22])

• On Aunt Marguerite’s Defiance:

  “You will not address me as ‘hun’ in a court of law.” —Judge ([13:45])

• On the Rite Aid Lawsuit Victory:

  “She got 1.2 [million]…and for the family, it was party time.” —Ryan ([34:07], [34:20])

• On the Newfound Wealth:

  “‘We’re millionaires, we’re out of the city!’ Y’all went right here—Rosedale.” —Ryan ([35:04])

• On Being Saved by Luck and Family:

  “The dynamics of our family…it saved me and Gary from going to prison because it got us out of a neighborhood.” —Tim ([37:33])

Important Segments & Timestamps

• Family History & O’Donnell Heights: [03:53 – 05:04]
• Fight Club Childhood: [08:03 – 10:06]
• Dad’s Craziness & Beer Can Incident: [10:46 – 11:43]
• Dad’s Courtroom Drama & Love Song: [12:28 – 14:54]
• Train Track Stories & Overpass Snow Battles: [16:26 – 19:38]
• Teenage Misadventure at Jennifer’s Party: [22:15 – 27:36]
• Rite Aid Lawsuit and Moving Up: [32:54 – 35:41]
• Family Table/Paulbearer Comedy: [39:24 – 40:17]
• Matriarch Power, Family Heirlooms: [42:00 – 43:22]

Final Reflection

This episode is a tour through wild Baltimore nostalgia, with both Ryan and Tim blending raw honesty with warm-hearted humor. Through stories of adversity—mental illness, poverty, brushes with the law—their love for family and the strength of old-school kinfolk shine through. It’s their matriarchs who provide lifelines, and absurd family antics that ground them both. The tone is unvarnished, often laugh-out-loud, frequently sentimental, and always colored by their uniquely Baltimore flavor.

Top Takeaway:
Legacy is messy, family is everything—and sometimes survival is just learning to laugh at the chaos.