Boston's First Black Police Commissioner - William Gross | Better Bad Ideas w/Sean O'Brien | Ep. 74

Boston's First Black Police Commissioner - William Gross | Better Bad Ideas w/Sean O'Brien | Ep. 74

From Better Bad Ideas with Sean O'Brien by 7EQUIS

June 24, 2026 · 1h 33m

About this episode

In this episode, Sean O'Brien interviews William Gross, Boston's first Black police commissioner, discussing his journey and the challenges of leadership in law enforcement.

Special thanks to our Launch Sponsor, Keches Law Group! Visit https://www.KechesLaw.com for your legal needs. This episode is also brought to you by LaborFirst, the leader in healthcare navigation and advocacy for plan sponsors, union members, and retirees. Visit https://laborfirst.com/ for more information. New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts! Chapters 03:10 Harry Wilson 10:26 Breaking social stereotypes 15:30 Charles Stuart 23:24 You want change, be the change 26:20 Whitey Bulger story 34:30 Leveraging Authority 37:27 Detective SGT. to first black Superintendent in Chief 47:29 Success has 1 million fathers, failure is an orphan 1:03:17 Stepping up, no Ego 1:08:10 Learn from each other 1:17:45 Toughest part about being Commissioner 1:20:45 Empathy, Sympathy, Care, Respect 1:27:00 What do you do in retirement? 1:28:45 Lunch with anybody still alive? Better Bad Ideas • https://www.instagram.com/betterbadideas • https://www.tiktok.com/@betterbadideas • https://x.com/betterbadideas Subscribe to Better Bad Ideas on Spotify & Apple! •…

People in this episode

Host: Sean O'Brien

Guest: William Gross

Sponsors

Keches Law Group, LaborFirst

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