Howard Robertson had every reason to go down the wrong path. His parents died. His siblings were in the streets. But instead of following them he chose corrections — and over a 22 year career from the late 1970s to the early 2000s he rose from correctional officer to captain to deputy warden to warden of Rikers Island — the largest and most violent jail in America. In this episode of Locked In with Ian Bick, Howard pulls back the curtain on everything — from his brutal upbringing to what made him choose corrections to what Rikers Island looked like from the inside during its most violent era to the notorious inmates he encountered to how programs reduced violence to how politicians destroyed what it could have been to the problems with closing it and what the future of Rikers Island really looks like.
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#rikersisland #jail #truecrimestories
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Thank you to FACTOR & GLD for sponsoring this episode:
Factor: Head to http://factormeals.com/lockedin50off and use code lockedin50off to get 50 percent off and free daily greens per box, with new subscription only, while supplies last until 09/27/2026. (See website for more details).
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GLD: New customers get 40% Off with code LOCKEDIN at https://www.gld.com/
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Connect with Howard Robertson:
https://www.amazon.com/Student-Game-Become-Unstoppable-Smarts/dp/1977283896
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Hosted, Executive Produced & Edited By Ian Bick:
https://www.instagram.com/ian_bick/?hl=en
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Timestamps:
00:00 Howard Robertson's Unlikely Journey
01:12 Overcoming Tragedy and Choices
02:29 Early Mindset: Learning from Role Models
03:53 Shooting for the Moon: Mentorship & Goals
05:02 Rising Above Average Through Hard Work
07:01 Is Drive Innate or Learned?
07:42 Family, Bad Paths, and Purpose
08:03 Helping Inmates and Preventing Recidivism
09:36 From Speaking to Writing: Reaching Youth
10:16 Authenticity in Storytelling: Why the Book Matters
11:01 Personal Stories: Bullying, Friendship, and Impact
13:02 How the Past Shapes Leadership Style
14:47 Navigating Street Ties Inside Rikers
18:00 Inmate Politics and Safe Resolutions
21:22 Respect, Boundaries & Saying No
23:40 Life Lessons and Staying Clean
24:43 Sponsor Segment: Factor Meals
27:40 Entering Corrections: Career Choice
29:34 Knowing the Community: Double-Edged Sword
30:14 Respect, Fairness, and Avoiding Violence
32:00 Overcrowding, Programs, and Jail Services
34:49 Correctional Culture: Then and Now
36:32 Political Changes & Rikers' Decline
41:13 Burough Jails, Funding, and Flawed Solutions
44:43 Sponsor Segment: GLD Chains
45:56 Corrections Leadership & Barriers to Progression
47:13 Mass Incarceration, Bad Policy, and Population Issues
51:01 Physical Conditions & Racial Makeup
54:35 Bail, Releases, and Systemic Injustice
56:39 Promotions, Process & Rules of the System
01:00:31 Programs: Entertainment and Violence Reduction
01:03:35 The Winner's Dorm: Transforming Inmates
01:04:41 Solitary Confinement: Problems & Alternatives
01:08:06 Expanding Special Housing and Culture Change
01:10:44 Medical, Mental Health, and Malingering
01:13:36 Mental Health, Career Impact and Life After
01:14:50 Defining Real Success for Youth
01:15:55 Numbers that Shock: Mass Incarceration
01:17:00 Notorious and Celebrity Inmates
01:18:36 Retirement, New Mission, and Legacy
01:18:56 Biggest Takeaways: Excuse-Free Success
01:19:56 Book Recommendation & Final Thoughts
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