The Thief Who Shoplifted His Way To Millions

Michael Pollara claimed to police he stole a store full of goods during his time as a shoplifter.
7:30 | 11/29/14

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Transcript for The Thief Who Shoplifted His Way To Millions
Well, file this under how not to do your holiday shopping. Shoplifting. Matt Gutman got the truth about the five-finger discount. The toy story that the stores don't want you to know. Reporter: 'Tis the season for shopping. And as long as there have been shops, there have been shoplifters. But they're often lacking in style. This guy clumsily stuffs a chainsaw down his pants. Risky. While these two openly pick up a table and are anything but stealthy and they walk it right out the door. These fools are the foot soldiers of the five fingered discount. And then there are the princelings. Michael Pollara for one. There's Pollara now. Police say this unassuming 46-year-old has strolled out of hundreds of retailers over his career, carrying merchandise worth millions. You're the -- the mozart, the Lebron James of the business. You can say that. Reporter: Pollara sat down with us for an interview. Well, when he wasn't jumping out of his seat -- at first, he's coy. After all, you don't perfect the gift of the grab by giving up the goods. So, what did you do with the money from boosting? No, I am not telling. Reporter: Let me ask you this. Is it a living? Hell, yeah. Reporter: How much have you managed to take out of stores in your career? You've got the wrong guy. Reporter: The wrong guy? Really? Then, how did a man who runs a small water filter business manage to travel the world from Easter island to China to Africa, always in style? He says he's just got a whole lot of frequent traveler miles to burn. I don't know why you guys are mixing this travel with this boosting. It's -- it's, like, wrong. Reporter: But the denials started to break down and one of "20/20"'s most honest confessors emerged once we got out some props and asked him, hypothetically anyway, to demonstrate how he hid merchandise in large boxes to get it out of a store. Look, the box is open. You could put some DVDs in that box. How's that? You're doin' it kinda wrong there. You could probably -- two, four, six. You could probably put -- you could probably get six leapsters in there. Reporter: Watch the maestro at work. There he is on store security camera footage in a Florida kmart. He chooses a large box. This $35 baby car set. Finding a quiet spot, he ditches the toy inside. Then, this is where the money is made. Pollara is now stuffing electronic gaming pads into that empty box, three or four of them worth $100 each. His accomplices keep a watch out. Paid sidekick, Travis Simpson. And, believe it or not, Pollara's own mother Margaret. Next, he re-seals the box with tape to make it look untouched. Finally, mom and Travis Simpson check out. Up to $400 in toys hidden in this box. They pay just $35 and head out home free. Pollara had shoplifting down to a science. There's only five methods. Either it's on you, either -- if you're a female, it's in the purse. Either it's in a bag or it's in a shopping cart or it's in a box. Reporter: And that stuffed box was his forte, but making thousands of dollars of merchandize disappear right in front of the cashier takes some sleight of hand. And two key props. A teddy bear to help him seem to be warm and fuzzy. You buy a teddy bear. Oh, it's so cute. She'll never dream. Reporter: Prop number two. A sweaty bottle of cold water that he grabs to hand to the cashier. Hand them the water so their hand is wet. Reporter: Why would the hand need to be wet? She's gonna wipe it down. Reporter: That's important because he doesn't want her to touch the stuffed box, otherwise she might realize it's way too heavy. You lean over and let her scan the box. She's not gonna touch anything, still wiping her hand. Reporter: It doesn't work at this toys'r'us and the cashier does lift the box herself. Knowing the jig is up, he heads out the door. She then opens it up to find one, two, three, four boxes of legos hidden inside. How much do you think he netted that day that you followed him? Tens of thousands. rich Rossman of the Broward county sheriff's office caught on to one of Pollara's shoplifting sprees. maker off the shelf and stuffed it with electronic toothbrush heads, which are about $20 apiece and walked out with $300 or $400 when the -- it actually rang up for $20 or $30. So net profit of about $300. That was store one -- Reporter: Not bad. -- Of nearly two dozen that day. Reporter: Rossman and his investigators tracked Pollara all around the country for months. He tells me for a crook, Pollara had quite the work ethic. He was up bright and early and stole from dawn to the evening hours. I had to tell the -- call the wife and say, "I don't know when I'm coming' home." Reporter: Till they finally hauled him in, then spent hours alternately interrogating him. Who's the easiest to steal from? They all are. I can walk out of any place. Reporter: And flattering him. You're good at what you were doing. I know. Reporter: -- And exposing his Achilles' heel, his ego. Pollara can't help bragging about his extravagant exploits. Hey, how many states you think you've been in, working? One year I hit the whole 50. Oh, you did? Yeah, the whole 50. Reporter: Rossman admits he only caught this veteran shoplifter after Pollara made one rookie mistake. He used a frequent customer card at the many toys'r'us stores he hit, allowing the authorities to track his movements. In your 11 years, how much do you think you've taken from toys'r'us? Probably a whole store full. Reporter: It is only now that cops start getting the full scope of his enterprise. Much of his retail booty was sold through fences, but some he sold himself online. How much have you sold on Ebay? I have no idea. We know. We know it. Well, tell me so then I can -- A million dollars. Oh, wow. Is that good or bad? It's a lot of money! Reporter: In fact when they caught him, he was planning another trip. I'm going on a cruise. I'm flying to Anchorage and picking up the cruise from there. Reporter: He's got the nerve to ask his interrogators to cancel the ticket for him, but instead of Alaska, he went to jail. Ultimately, Pollara served just two years. My nickname in jail -- everyone has a jail name. I was toys'r'us. Reporter: What about his mother? She was sentenced to probation for acting as his lookout and now is sitting off-camera during the interview. I hate him and I love him. It's Italian love. Reporter: After two years in the clink, Pollara relishes his freedom. He wouldn't say where he's spending his time these days, but when I asked him what the easiest stores had been to hit, he gave us perhaps a hint. I can't tell those because you don't know. I might be in those. Next --

This transcript has been automatically generated and may not be 100% accurate.

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