TRIGGERnometry Podcast Summary

Episode: I Spent Years on Skid Row, Homeless & Addicted – Jared Klickstein
Date: July 13, 2025
Hosts: Konstantin Kisin, Francis Foster
Guest: Jared Klickstein, author of "Crooked Smile"

Overview

In this gripping episode, Jared Klickstein recounts his harrowing journey through homelessness and drug addiction on Los Angeles' Skid Row. He discusses the personal and policy-driven forces behind today’s homelessness and addiction epidemics, drawing from years of lived experience, and offers unvarnished insights into what works, what doesn’t, and how the system routinely fails those it purports to save. The conversation explores the realities of street life, family background, the impact of drug policy, and the search for hope and meaning when institutional supports fail.

Key Discussion Points & Insights

1. Jared’s Early Life and Descent into Addiction

• Family Background & Early Trauma
  • Jared grew up in Boston with both parents addicted to heroin, witnessing erratic behavior, paranoia, and trauma from an early age.
  • “Playing catch with my dad was like, doing a perimeter check around the house with a gun.” – Jared [04:55]
• Teen/College Years & First Contact with Hard Drugs
  • Adopted by extended family at age 12 after alerting relatives to his parents’ drug use.
  • In college at UC Santa Cruz, exposed to heroin and OxyContin, which spiraled quickly into full-blown addiction.
  • “Alcohol fixed that to some extent, but OxyContin didn’t have a hangover. And it just really got to the point and it fully enveloped my entire life within, you know, a month or two, probably.” – Jared [08:24]

2. Life on Skid Row

• Skid Row in Reality
  • Described as terrifying, violent, with visible blood, bodies, and rampant mental illness and addiction.
  • “...thousands of people just, you know, out and about really in a zombie stage...You’d walk by, you see pools of blood, sometimes dead bodies.” – Jared [17:07]
• Survival and Hustling
  • Earned money through panhandling and later shoplifting, particularly after decriminalization policies enabled large-scale retail theft.
  • “I was making, you know, three to $500 a day in cash shoplifting… I made six figures, probably untaxed.” – Jared [15:29, 15:43]

3. Addiction, Crime, and Policy

• Relationship Between Policy & Street Reality
  • Decriminalization measures (e.g., Prop 47 in California) made it easier for addicts to fund their habits through crime.
  • “The state currently in places like California are doing everything in their power to make it as easy as possible to keep getting high.” – Jared [45:37]
• Police, Jail, and the Cycle of Release
  • Jail served as the only place Jared could get sober, though it was not a real solution: “I had a wonderful time. It was one of the, probably the greatest times of my life... I finally got a bed and a pillow, and I just didn’t have any responsibilities.” – Jared [31:59, 32:02]
  • No meaningful re-entry programs post-release; typically dumped right back onto Skid Row at 2am. Without structure or sober housing, relapse was immediate.

4. The Role and Experience of Jail

• Social Structure: Gangs, Racial Alliances, and Survival
  • Explained the racialized gang structure in LA County Jail, his experience as a half-Jew joining the “Peckerwoods,” and the surprising dynamics between ethnic groups.
  • “When you go to LA County Jail, you have to join a gang... The gangs are racially based... if you’re white, you have to join the Peckerwoods...” – Jared [32:59]
• Violence & Rules
  • Most violence is in-group, and follows strict codes for ‘respect’ among factions. “The majority of the violence is actually inflicted by your own race to show respect to the other races if something disrespectful occurs.” – Jared [39:49]

5. Fentanyl and Today’s Crisis

• The Shift from Heroin to Fentanyl
  • Fentanyl is now the prevalent opiate, far more dangerous and incapacitating than heroin ever was.
  • “Heroin, you can... function partially. There’s no functioning on fentanyl... it’s like you snap your fingers and you are a zombie.” – Jared [21:19]
• Harm Reduction vs. Tough Love
  • Jared critiques California’s “housing first” policies, which delink sobriety from housing or benefits: “It’s essentially a, a fentanyl housing program now.” – Jared [31:07]
  • Expresses that meaningful consequences, such as legal jeopardy or mandated treatment, are often the only way to force a hard reset.

6. Personal Recovery: Hope, Work, and Self-Sufficiency

• Finding Meaning Through Work
  • Building carpentry skills, getting a construction job, and finding a rehabilitative nonprofit program put Jared back on a path to recovery and meaning.
  • “The reason why I was able to get off the streets and stay sober was because I saw some kind of path to self sufficiency and self esteem... with the carpentry stuff.” – Jared [60:45]

7. Policy Solutions and Critique

• Current Policy Failures
  • Argues that California’s huge spending on homelessness and addiction has only fueled the problem, with little accountability and rampant grift.
  • “California spent $24 billion on homelessness and addiction in the last five years. And until last year, the number just steadily climbed.” – Jared [48:39]
• Recriminalization and Mandated Treatment
  • Advocates a moderate return to criminalization for property crime, with options for mandated, long-term treatment instead of incarceration.

8. The Broader Social Context: Loss of Hope and UBI

• On the ‘Sickness’ of Society
  • Links the rising despair and addiction to downward mobility, lost opportunity, and the anxiety-producing labor market.
  • “There is just a loss of hope… If you’ve got hope, you’re probably gonna be okay. The moment the real darkness sets in is when you see no hope.” – Francis [60:13]
• Universal Basic Income Skepticism
  • Questions whether UBI would offer relief or simply entrench harm: “If someone came in and gave you a thousand dollars a month, wouldn’t you just stay on skid row forever taking those drugs?” – Konstantin [65:38]
  • Jared reflects that without purpose or structure, money only enables more self-destructive behavior.

Notable Quotes & Memorable Moments

• On addiction and family trauma:
  “Playing catch with my dad was like, doing a perimeter check around the house with a gun.” – Jared [04:55]

• On policy failure:
  “The state currently in places like California are doing everything in their power to make it as easy as possible to keep getting high.” – Jared [45:37]

• On the lived “economy” of homelessness:
  “I made six figures, probably untaxed, and usually went to sleep with $0.” – Jared [15:43]

• On jail as a ‘respite’:
  “I finally got a bed and a pillow, and I just didn’t have any responsibilities. And I just knew that, like, my one task was, like, to not just to get off heroin…” – Jared [32:02]

• On joining a jail gang:
  “I wasn’t excited to join a race gang, but, you know, when you went in Rome, you know, you join a race gang, and if you’re white, you have to join the Peckerwoods…” – Jared [32:59]

• On meaning and work:
  “We need to create opportunity. I mean, the reason why I was able to... get off the streets and stay sober was because I saw some kind of path to self sufficiency and self esteem...” – Jared [60:45]

• On giving out money or housing to addicts:
  “You will take anything given to you and try to convert it into a way to get drugs if you are terminally addicted to drugs.” – Jared [65:52]

Important Segment Timestamps

• Skid Row Reality: [17:07]
• Addiction Begins – College & OxyContin: [08:24]
• Policy of Decriminalization and Crime: [15:09]; [45:37]; [48:39]
• Experience in Jail – Gangs & Detox: [32:02]; [32:59]; [39:49]
• The Fentanyl Crisis: [21:19]
• Recovery and Finding Meaning: [60:45]; [43:57]
• Critique of Universal Basic Income for Addicts: [65:38]; [65:52]

Conclusion & Final Thoughts

The episode offers a stark, personal portrait of the intersection between addiction, policy, hope, and recovery. Jared’s story is deeply humanizing and disturbing, laying bare the failures of both punitive and permissive policies while highlighting the absolute need for purpose, opportunity, and real accountability.

Final question:
When asked what’s not talked about enough, Jared warns of looming economic shifts from AI/automation and the urgent need to create new forms of meaning and stability for those left behind.
“I just really think we need to actually formulate a real plan... What does society look like if 50% of people are out of work and 50% aren’t? Where does this go?” – Jared [64:11]

The hosts and Jared agree: hope, work, and dignity are essential – and can’t be replaced by handouts alone. The system, as currently constructed, is failing, and meaningful solutions require difficult, mature political choices and genuine compassion rooted in wisdom, not wishful thinking.