Episode Details

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.

_____________________________________________ #rikersisland #jail #truecrimestories

_____________________________________________ 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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_____________________________________________ Connect with Howard Robertson: https://www.amazon.com/Student-Game-Become-Unstoppable-Smarts/dp/1977283896

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ 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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