This Past Weekend w/ Theo Von #616 - Retired Boston Detective
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Oct 9, 2025 Kara Connolly, a retired Boston detective with over 31 years in law enforcement, shares her gripping experiences from undercover work in the Human Trafficking Unit. She discusses the stark contrasts between traditional policing and today's modern methods, alongside her notorious john stings targeting buyers. Listeners will hear tales of a shocking infant rescue and a major multi-state trafficking investigation that earned her Detective of the Year. Kara offers insights into the pressures of policing, societal perceptions, and the emotional toll on officers and their families.
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Early 1990s Patrol Reality
- Kara describes early patrol work in Dorchester and South Boston during the violent 1990s.
- She contrasts high homicide rates then with much lower modern totals and a quieter South Boston beat.
How To Become A Detective
- To become a detective in Boston, prepare for lengthy exams and interviews and study multiple textbooks.
- Expect different duties, civilian clothes, and responsibility for owning cases and court follow-up.
Fast Teamwork Solved A Robbery
- Kara recounts an armed robbery at a cellphone store where quick patrol response and forensic finds led to arrests.
- The suspects received long federal sentences after evidence and interstate gun links emerged.