The Story

The prison chief linked to organised crime - the Sunday Story

4 snips
Aug 24, 2025
Gabriel Pogrund, the Whitehall editor at the Sunday Times, delves into the chaotic world of Wandsworth Prison, Britain’s infamous jail. He reveals the disturbing realities of overcrowding and rampant corruption, shedding light on the controversial figure Bobby Cunningham and his questionable ties to organized crime. The discussion highlights the dire need for systemic reform and raises serious concerns about the integrity of prison officials and the safety of inmates. Through Pogrund's insights, listeners gain a gripping perspective on a troubled prison system.
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INSIGHT

Wandsworth As Symbol Of Systemic Failure

  • HMP Wandsworth is a large, overcrowded, Victorian-era Category B prison with systemic safety and security failures.
  • Gabriel Pogrund describes its conditions as lawless, with pervasive drugs, violence, drones and severe overcrowding.
ANECDOTE

Rapid Rise Despite Early Scrapes

  • Bobby Cunningham rose rapidly from Isle of Sheppey roots to senior roles despite early disciplinary scrapes.
  • He had alleged incidents including a suspension for requesting an assault and customs intercepting martial-arts weaponry sent to his home.
INSIGHT

Promotion Without Formal Qualification

  • Cunningham became head of security and then interim deputy governor despite not passing governor exams.
  • His rapid promotion and interim status raised suspicion among colleagues about suitability and oversight.
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