From Chicago Prosecutor to FBI SWAT: A Conversation with Jon Dubin

Today’s guest is Jon Dubin—former prosecutor, FBI Special Agent, SWAT Operator, and now the managing partner of Pineapple Brothers Lānaʻi.

Jon began his career in the Cook County State’s Attorney’s Office prosecuting violent crimes before joining the FBI in 2003. Over his time with the Bureau, Jon specialized in counterintelligence, gangs, and counterterrorism. He served as a SWAT operator for 13 years, trained agents as a firearms instructor, and was assigned to the Oakland Police Department-FBI Homicide Task Force. He finished his time in service on the Joint Terrorism Task Force.

In this episode, Jon shares how he went from prosecuting domestic abuse cases, to chasing gang members and terrorists with the FBI, to building a luxury hunting business in Hawaii - with wild stories from the courtroom, the streets, and the islands.

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