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

The Jack Carr Channel

Jack Carr

Society & Culture

4.9 • 2.8K Ratings

🗓️ 16 July 2025

⏱️ 81 minutes

🔗️ Recording | iTunes | RSS

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Summary

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. FOLLOW JON Instagram: @pineapplebrotherslanai Website: https://pineapplebrothers.com/about-us/ Website: https://www.highadventurecompany.com/ FOLLOW JACK Instagram: @JackCarrUSA X: @JackCarrUSA Facebook: @JackCarr YouTube: @JackCarrUSA SPONSORS CRY HAVOC – A Tom Reece Thriller https://www.officialjackcarr.com/books/cry-havoc/ Bravo Company Manufacturing - https://bravocompanyusa.com/ and on Instagram @BravoCompanyUSA THE SIGs of Jack Carr: Visit https://www.sigsauer.com/ and on Instagram @sigsauerinc Jack Carr Gear: Explore the gear here https://jackcarr.co/gear

Transcript

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0:00.0	This episode of the Danger Close podcast is brought to you by Cry Havoc.
0:04.5	From New York Times number one bestselling author, Jack Carr.
0:08.6	Cry Havoc, a Tom Rees thriller.
0:11.3	Order Now.
0:13.2	I remember one of the first ops, it was wintertime.
0:16.0	Right by the front door, these people had this chimney where out popped freaking Santa Claus.
0:22.1	What?
0:23.1	Every 30 seconds.
0:24.1	Oh, geez.
0:25.1	Ooh, who, who, who, who, who, dude, I snapped up on Santa Claus.
0:28.6	Oh.
0:29.6	It would be my first off.
0:30.6	I'm like, if I'd shot Santa Claus, it would be my last off, first of all.
0:34.6	Well, you would have a new nickname.
0:36.1	Exactly.
0:36.6	Scrooge.
0:40.0	Exactly. Exactly.
0:52.2	Man, thank you so much for taking the time to do this.
0:55.2	I want to ask you all about being a prosecutor, FBI agent, but I want to start with what you're
1:00.2	doing now, what we're doing now, out in Lanai.
1:04.5	And yeah, yeah, I mean, access to your muflon sheep, hunt out of the four seasons.
1:09.2	Give us a little rundown, but before that, look, I have behind me. I'm not sure if you can see it in your angle or not, but a buddy just stopped by and dropped off a tradbo that he made. So Trevor Thompson dropped off this thing. He's been studying how to make in the last couple of years and made me a knife of an obsidian blade right there that he made himself, the arrows,
	...

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