The Gamble | Episode 2

Summary

Deep Cover: The Family Man – Episode 2: "The Gamble"

Release Date: May 18, 2026
Host: Jake Halpern (Pushkin Industries)

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Episode Overview

In this riveting installment of Deep Cover: The Family Man, investigative journalist Jake Halpern delves into the complex double life of Keith Giamanco—a seemingly average suburban father who became the serial bank robber infamously known as "The Boonie Hat Bandit." Halpern travels deep into the Ozarks to meet Keith, unraveling his journey from devoted dad to criminal, and the difficult personal choices that led him there. Through candid interviews with Keith and Detective John Bradley, the episode explores themes of family secrets, desperation, calculated risk, and self-deception.

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Key Discussion Points & Insights

1. Setting the Scene: A Visit to Keith in Exile

• [04:24–07:50]
  Jake narrates his tense drive down a remote, wintry Ozarks road to Keith Giamanco’s isolated cabin, underscoring Keith’s new life away from civilization.
  • Keith, now tending goats and dogs by a stove, describes his contentment with this simple, reclusive lifestyle.
  • Keith: "My day is pretty much spent here. I tend to, you know, the animals and cleaning up the house... it's not anything that I begrudge doing." ([08:20])

2. Keith’s Family History & Upbringing

• [10:23–13:13]
  • Raised by a single mother, Keith never knew his father, shaping his vow to provide a stable, loving home for his own children.
  • Keith: “He was non-existent in my childhood. He left when I was six months old, so I only knew a household with my mother.” ([11:41])
  • He recounts his efforts to grant his daughters, Elise and Marissa, a “storybook” suburban childhood, centered on family traditions and stability.

3. Marital Breakdown & Financial Strain

• [13:13–15:31]
  • Keith recalls the moment he discovers his wife Becky’s addiction-fueled debts, which wiped out their credit and forced her abrupt departure.
  • He processes the aftermath by throwing himself into single parenthood, therapy, and enrolling his daughters in a supportive all-girls Catholic school.
  • Keith: “It was rewarding... but also very stressful and a lot of anxiety, especially when there’s not the resources there to provide the way you want to for your children.” ([15:13])

4. The Lure of Risk: From Trading to Robbery

• [15:31–17:09]
  • To make ends meet, Keith pivots from blue-collar work to day trading, cashing out his retirement to chase stock market gains.
  • He likens day trading to calculated risk, in contrast to gambling:
    • Keith: “Gambling is a non-calculated risk. Trading the market… is a calculated risk.” ([16:33])
  • Details how desperation and “wishful thinking”—what he calls “smoking hopium”—led him down a perilous path when the 2007 recession hit.

5. Crossing the Line: Deciding to Rob Banks

• [20:37–23:07]
  • Keith confides his mounting debts to his mother; her joke about robbing a bank plants a seed. He methodically researches FBI data on avoided mistakes.
  • He rationalizes robbery as "chunk yardage" (a football metaphor for making big, risky plays under pressure).
    • Keith: “It made more sense… to get chunk yardage instead of two yards in a cloud of dust.” ([22:43])
  • With carefully chosen disguises and avoidance tactics, Keith targets local banks, using notes to avoid violence.

6. The Mechanics of the Heist

• [24:28–25:56]
  • Keith’s first robbery: walks in nonchalantly, presents a note, walks out with over $6,000.
    • Keith: “I went up and I handed her the note... filled it with money, and I turned around and casually walked out….” ([24:28])
  • He describes feeling relief rather than stress, noting authorities didn’t have a clear image or vehicle identification.
  • Becomes emboldened, rotating disguises — different hats, hair dye, shaving — to avoid recognition.
    • Keith: "I would dye my hair jet black sometimes. ... There was even a couple of times where I would grow a beard and then shave in the car." ([26:30])

7. Detective John Bradley Enters the Chase

• [27:07–30:49]
  • Detective Bradley notices a pattern of meticulously executed, yet unkempt and nervy, robberies by a man with a boonie hat.
    • On potential violence:
      • Bradley: “When you have a suspect that is nervous, he's unsettled. That can lead to violence quickly.” ([29:03])
    • On the use of hidden hands to imply a weapon:
      • Bradley: “By doing that, you’re implying... that you have a weapon... If he wants you to believe he has one, he probably has one.” ([29:59])
  • As the “Boonie Hat Bandit” label spreads, Bradley intensifies his efforts to prevent tragedy and catch the culprit.

8. The Double Life & Rationalization

• [35:50–39:10]
  • Keith struggles to reconcile loving fatherhood with criminal secrecy:
    • Jake: “Did you find it difficult at all to look your daughters in the eye while this was happening?”
    • Keith: “I wasn't very good at looking anyone in the eye at that point… you can't share anything like that with someone else. If you do, you're had.” ([35:50])
  • He succumbs to “manifesting” culture, believing positive thinking will keep his life intact, a philosophy drawn from the self-help book The Secret.
    • Keith juggles criminality and domestic chores as if living parallel lives:
      • Jake: “Rob bank, pick up girls at school, mow grass.”
      • Keith: “Yeah, that's pretty much what it was.” ([39:08])

9. Escalation: Two Heists in One Day

• [39:28–43:25]
  • When a single robbery comes up short, Keith brazenly robs a second bank the same day—even returning to a branch he’d already hit.
  • He rationalizes this as unforeseen and thus, less risky:
    • Keith: "If you had never robbed two banks and went on a one day spree… it would be least expected to happen.” ([40:38])
  • Deposits $14,000 in stolen cash to rescue his house from foreclosure, weaving truthful elements into his alibi at his own bank:
    • Keith: “I was gathering money to save our home from foreclosure. Which was an honest answer now by omission. There's a lot of dishonesty there. Correct?” ([42:42])

10. The Limits of Self-Deception

• [43:25–45:16]
  • Keith sets a goal of $140,000 as his “quit number,” echoing classic gambler’s delusions of control.
  • Jake notes that while Keith lied to others, the most destructive lies were the ones he told himself about control and justification.
  • Jake: “His story kept on reminding me that the most dangerous lies are always the ones we tell ourselves.” ([44:42])

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Notable Quotes & Memorable Moments

• On personal responsibility:
  Keith Giamanco: “People say, 'Oh, you made a mistake.' No, I didn't make a mistake... I made bad choices. Those things were a choice. They weren't a mistake. I purposely did what I did.” ([09:43])

• On desperation and risk:
  Keith Giamanco: “It seemed very crazy, but also I felt a sense of being so desperate that I felt it was the quickest, easiest way out.” ([36:59])

• On manifesting optimism:
  Jake Halpern: “It may sound simplistic, but this whole idea of manifesting—it was very much in vogue at the time. There was a wildly popular self help book... Keith had read it and embraced its philosophy.” ([37:32])

• On the logic of escalation:
  Jake Halpern: “He decides to rob a branch... that he’d already robbed five months prior. It almost seemed like he was daring them to recognize him. But the crazy part is, it works.” ([40:50])

• On lying and self-deception:
  Jake Halpern: “Lies and the truth have a strange relationship with one another... you need to back the lies into the corners or the gaps.” ([43:25])

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Key Timestamps

| Timestamp | Topic/Highlight | |-----------|-------------------------------------------------------------| | 04:24–07:50 | Jake arrives at Keith’s remote cabin; meeting Keith | | 10:23–13:13 | Keith’s childhood, vows made after father’s abandonment | | 13:13–15:13 | Marital breakdown and family financial crisis | | 16:33 | Keith’s philosophy on risk: trading vs. gambling | | 22:43 | Keith’s football metaphor: “chunk yardage” | | 24:28–25:56 | First robbery: method and aftermath | | 26:30 | Disguises and the mechanics of not getting caught | | 27:41–30:49 | Detective Bradley’s perspective and worries | | 35:50–36:59 | The emotional toll and compartmentalization as a parent | | 37:32 | The influence of “manifesting” on Keith’s decisions | | 39:28–43:25 | The two-robbing day and post-heist rationalization | | 44:42 | Reflections on deception—oneself and others |

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Closing Thoughts

This episode masterfully dissects the gradual slide from desperation to criminal enterprise, exploring the intersections of love, shame, self-rationalization, and risk. Both Keith and those pursuing him—especially Detective Bradley—offer nuanced, human portraits of the costs and consequences of living a double life. The narrative highlights not only the mechanics of deception, but the emotional fallout for both the deceiver and his unsuspecting family.

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Next Episode Preview

Cliffhanger: The police close in as Keith’s desperation grows; the double life threatens to unravel.

• Detective Bradley: “My partner and I... would go out during different times and just kind of ride the area. That day... we were out already when the call came out.” ([45:16])
• Sophia Donner: “I just was angry at the living of a double life... There's the boony hat bandit and there's Keith Giamanco.” ([45:39])

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Transcript

[Sophia Donner]

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[Keith Giamanco]

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[Jake Halpern]

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[Jake Halpern]

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[Keith Giamanco]

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[Jake Halpern]

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[Sophia Donner]

Marissa and I were in our respective rooms when I see a flashlight coming through my window. And then I see several flashlights and then I hear dogs. They're all like knocking really loud. Like, open the door. And you could just feel the pressure. Like, dude, they're gonna open this door if we don't open this door. The picture that was on Fox 2 News, you could see into the car from this helicopter shot and there was a cup. You're like, that's dad's emo's cup. I realized that my dad has done something wrong and I immediately started feeling like this is gonna change my life and my family dynamic.

[Jake Halpern]

Foreign I'm on a dark and dirt road in the Ozarks. I'm going like 15 miles an hour because I keep getting stuff caught on the undercarriage of the car that's dragging. It's totally dark.

[Keith Giamanco]

Whoa.

[Jake Halpern]

Wow. This is me last winter in a rental car in a remote part of Missouri. And even with my brights on, it was hard to see. The road kept twisting and turning and climbing. And just as I was navigating all of this, my phone rang. Are you okay there? Yeah, I'm fine. I'm actually. I'm good. I'm almost there. That's my wife, Kasha, and she's been tracking my progress on her find my app. To her, it looks like I'm just a little too far off the grid. Okay. I'm totally fine. Totally fine. We're good, we're good. But I need to focus on this road. That little beep, beep, beep. That's the sound of my phone dropping her call. My GPS says I'm getting close to my destination, like about to arrive. It says we're 600ft. This is crazy. Whoa. I'm trying to slow down here to not destroy this car. I mean, Arriving. How could we be Arriving. There's nothing here. Oh, hold on. There's a driveway. I mean, I'm just gonna hope this is right. I pull into this driveway, but I mean, honestly, it just looks like a break in the trees, Like a clearing, nothing more. With a cabin at the edge of it. And then I see a shadowy figure emerge from the cabin, waving his hand. Keith. Holy cow, man. You guys live out here?

[Keith Giamanco]

Yeah, and we don't have any outdoor lighting yet.

[Jake Halpern]

Good to see you, Jake.

[Keith Giamanco]

Nice to meet you, Jake. He's just pulling right there.

[Jake Halpern]

All right. This is the man that I've traveled a very, very long way to see. Keith Giamanco, dad of Elise and Marissa, the twin sisters who you heard from in the last episode. They described him as a loving but kind of mysterious father. And they told me they really had no clue what he was up to until one day when he appeared on the local news being hunted down by the police. As for how Keith got here to this remote spot deep in the Ozarks, well, that's a very long story. And really it's the story I'd come to hear for myself from Keith in his own words.

[Keith Giamanco]

To see you. Yeah, likewise, Major.

[Sponsor Voice / Advertiser]

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[Jake Halpern]

Lots of dogs.

[Keith Giamanco]

It's back here, isn't it?

[Jake Halpern]

Oh, you're, you're, you're. I mean, I've traveled some and you guys are. You guys are back there.

[Podcast Host / Narrator]

Okay, I'm right with you.

[Keith Giamanco]

Been an adjustment.

[Jake Halpern]

Keith leads me towards the cabin. All around us are goats and dogs and heaps of snow. The cabin itself is very orderly. There's a set of rakes leaned up against the outside wall, perfectly aligned, arranged just so. Once we're inside, we sit down by a fire crackling in a wood burning stove.

[Keith Giamanco]

My day is pretty much spent here. I tend to, you know, the animals and cleaning up the house, doing laundry and things like that. And I'm good with that. I mean, I did it before, you know, when I was a single parent, so it's not anything that I begrudge doing.

[Jake Halpern]

What do you do with the animals?

[Keith Giamanco]

Oh, gosh, everything. I watch them have fun a lot. They like to have fun, especially the dogs. They go in and out a lot and play outside. And I love them to death.

[Jake Halpern]

If Keith sounds like a jolly old grandpa kind of guy, he kinda is. He's got this friendly midwestern look. Short graying hair, neatly combed, a bright, almost boyish smile. He looks like the kind of guy who'd stop and help jumpstart your car. But appearances can be deceiving and I knew from speaking to his daughters that there was so much more to Keith. In many ways, he was the sphinx that drew me into this story. I wanted to know who lived beneath that veneer.

[Keith Giamanco]

Life is about choices and moving forward. That molds how you live your life. Those choices, I personify that I'm not immune to it, that's for sure. People say, oh, you made a mistake. No, I didn't make a mistake. Making a mistake is putting salt in your coffee instead of sugar. I made bad choices. Those things were a choice. They weren't a mistake. I purposely did what I did.

[Jake Halpern]

These choices that Keith made, they're what brought a small army of law enforcement to his front door and what led to that police chase with the helicopter overhead. And what many years later, ultimately ended with him here in a remote cabin in the middle of nowhere. I'm jake halpern, and this is deep cover the family man episode 2 the gamble. Keith was raised by a single mom. He says he was always very close with her. She raised Keith and his three siblings on her own. Keith was the youngest by a lot, and in many ways he grew up as an only child living a very solitary life. His mom worked long hours at a restaurant and with the other kids grown up and gone, Keith spent a lot of time alone in the house. He says he barely knew his father at all.

[Keith Giamanco]

He was non existent in my childhood. He left when I was six months old, so I only knew a household with my mother.

[Jake Halpern]

What kind of impact did that have on you?

[Keith Giamanco]

It had a huge impact because I made a vow to myself and to them that I would be there for him.

[Jake Halpern]

When Keith had children of his own, he wanted his girls to have the kind of storybook childhood that he didn't have. A real classic family life. At the center of this life was Keith's wife, Becky.

[Keith Giamanco]

She was a very fun, loving person. She was an excellent wife and mother. For the first seven years of our marriage, she was a stay at home mother. She was very attentive to the children. She was a wonderful housekeeper and cook and a good friend.

[Jake Halpern]

Though Keith was quick to add, their marriage wasn't perfect, especially as the girls got older.

[Keith Giamanco]

There was some rocky moments, of course, because our personalities clashed in a lot of ways and she was sometimes a difficult person for me to get along with.

[Jake Halpern]

How so?

[Keith Giamanco]

I guess I would say her. Her love for the home life wasn't constant.

[Jake Halpern]

Keith told me about the moment when he realized all was not as it seemed with Becky.

[Keith Giamanco]

I remember there is a like a Founders Day Parade in my hometown of Florissant, Missouri, and everybody gathers and you have the family over. And I wanted to pick up a few things for entertainment purposes. And I went to get a credit card out of my desk and she broke the news to me when I was getting in my desk that every single one of them were charged to the hilt. We had nothing. We had no credit of any kind because she had ran it all up with drugs and alcohol.

[Jake Halpern]

Not long after this, Becky moved out. I kept thinking about how Keith had described his wife to me, how he'd paused and then very carefully chosen these. Her love for the home life wasn't constant. This, as I came to learn, was a classic Keithism, a midwestern riddle of banality whose darker and truer meaning had to be ferreted out. And I also realized that this was probably the type of thing that Keith had said to his daughters when they were growing up. A sanitized version of the truth that was so sanitized that it was no longer really the truth at all. Keith says that he quickly embraced the role of being a single dad. He cooked the dinners and did the laundry. Also put his daughters into therapy because he he understood that they needed someone to talk to about what had happened. He also transferred them to an all girls Catholic school where he felt they could get more support emotionally and academically. Without his wife around, Keith felt that all of this was on his shoulders. What's that like for you?

[Keith Giamanco]

Rewarding and fulfilling in a lot of ways, but also very stressful and a lot of anxiety and especially when there's not the resources there to provide the way you want to for your children.

[Jake Halpern]

Yeah. So let's talk about his resources. Keith had started out as a regular blue collar guy. When his girls were little, he worked at a printing press, coming home each night with ink stained hands. Then in the early 2000s, around the time that his wife moved out, Keith reinvented himself. And as a day trader, he cashed out his retirement plan and started buying and selling stocks. At the time, the market was booming. He says he did well day trading. Though Keith says that sometimes he lived beyond his means. For a while, he dated a dentist and he spent money to impress her, Going on trips and dining out, trying to create an image of wealth and success. For a while, it worked. Keith attributed his financial success to how closely he studied the stock market. He prides himself as someone who understands how systems work.

[Keith Giamanco]

A lot of people like to say, well, it's like gambling. No, it's not like gambling. Gambling is a non calculated risk. Trading the market. Anybody who knows anything about the market and the way it moves it is a calculated risk.

[Jake Halpern]

Keith told me there was only one real trap. Wishful thinking. Believing the version of things you want to be true.

[Keith Giamanco]

In the trading industry, they call it, you know, you don't want to make a trade and then smoke hopium on it.

[Jake Halpern]

Smoking hopium. I hadn't heard that phrase before, but the meaning it landed immediately. Hope. It's useful. It's necessary even. It's what gets people to try things that might fail. But Keith, he was talking about something else. He was talking about the moment when hope mixes with desperation and suddenly you're no longer seeing things as they are, but as you need them to be. By the fall of 2007, the economy had begun to slide into what would the Great Recession. The market was faltering and so were Keith's finances. He was a 43 year old single dad and broke. He owed about $45,000 in back taxes, he was behind several months on his mortgage payment, and he couldn't afford the tuition at his daughter's private high school. He felt desperate and he would soon act on that desperation and in a way that would change the course of his life forever.

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[Jake Halpern]

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[Jake Halpern]

when his day trading started to flounder, Keith finally decided he had to open up to someone about how bad things had gotten. Someone who would understand the pressures of being a single parent. Someone who wouldn't be too judgmental. Someone who truly loved him. And what better person than his own mother, Margie, who lived right in the neighborhood? When Keith opened up, Margie listened patiently and at some point she made a joke. Kind of offhandedly.

[Keith Giamanco]

She just said, well, I hope you don't do something crazy like go rob

[Jake Halpern]

a bank explicitly warning you not to do this.

[Keith Giamanco]

Yes.

[Jake Halpern]

So how do you flip that on its head and decide that that's a good idea?

[Keith Giamanco]

Because I started to do research.

[Jake Halpern]

Tell me.

[Keith Giamanco]

Looking at the FBI website specifically, and looking at how people got caught and basically learning what not to do in order to get away with robbing a bank.

[Jake Halpern]

Yeah, around this time, when Keith was really in the hole, he decided that he should focus his efforts on learning how to rob a bank. He soon became an expert on all manner of things, including the use of dye packs, the positioning of security cameras, and the best getaway routes. Keith even figured out the ideal time to strike, midday, right after lunch, when people were a little sluggish. Keith's plan was not to carry a weapon, just a demand note saying, give me all the money in both drawers and we'll all go home safe. Now you might be thinking, wait, wait, wait, hold up. There's gotta be another way. Why not get a job, any job at all, working the counter at McDonald's or Burger King. Anything legal. I asked Keith about this.

[Keith Giamanco]

You're going to work this menial job and it's not even going to come close to covering what is due. And you're still going to lose everything and you're still going to be working at Burger King. It Made more sense in football terms to get chunk yardage instead of 2 yards in a cloud of dust.

[Jake Halpern]

Yeah, but it's like you're going for it on 4th and 17.

[Keith Giamanco]

Yeah, absolutely.

[Jake Halpern]

4th and 17. That's football speak for a long shot. A big play born out of desperation, but that keeps you in the game. And that's what Keith wanted. A big payday that solved everything. Only problem was, his whole life and his daughter's lives hung in the balance. Eventually, Keith settled on his first target, a Bank of America in St. Charles, Missouri. And in November of 2007, he decided it was time. He dressed for the occasion in a green fatigue jacket and a camo hat with a wide brim that shadowed his face. Keith parked a safe distance from the bank and then got out of his car. Did you have any last minute doubts before you walked in?

[Keith Giamanco]

Sure. Absolutely. There were thoughts of aborting it, of course. Should I or shouldn't I do this?

[Jake Halpern]

But in the end, he walked into the bank, he looked around, and he felt relieved to see that no one was paying any attention to him. So he got in line like any other customer, and he waited to see the teller.

[Keith Giamanco]

I went up and I handed her the note, Slid her across a manila envelope. She filled it with money, and I turned around and casually walked out across the parking lot to the car, which was behind the gas station, and pulled straight out onto the exit of the highway and drove home.

[Jake Halpern]

There's something so humdrum about the way he tells this story, this total absence of drama, which is precisely what Keith had been hoping for. This was his proof of concept. When he got home, Keith counted the money. Over $6,000 in cash. After that first robbery, Keith watched the local news, and there he was, captured by the surveillance cameras in the bank. Did it stress you out to see yourself?

[Keith Giamanco]

No, it would have stressed me out. If I was recognizable, that would have stressed me out. There was literally a feeling of relief when I knew that they didn't have a make on the vehicle, nor did they have a good picture of me, that somebody that I knew would recognize me for the $5,000 reward or whatever it was at that particular time.

[Jake Halpern]

Keith felt emboldened, and so he just kept on going, robbing more banks, and quickly became a middle aged Midwestern master of disguise. He kept changing his outcome, and he swapped headgear, baseball hat, bucket hat, boonie hat. Like he'd also robbed a hat store and was now trying on the whole inventory. Sometimes he wore a fleece, other times a sweater or a sport Coat. And then, of course, there's what he did with his facial hair.

[Keith Giamanco]

I would dye my hair jet black sometimes. And then, of course, when I got home, I would pull in the garage and go in and wash my hair. There was even a couple of times where I would grow a beard and then shave in the car.

[Jake Halpern]

Right in the car?

[Keith Giamanco]

Right in the car afterward.

[Jake Halpern]

Like an electric shaver?

[Keith Giamanco]

No, with just water and a regular razor. So I would immediately become clean shaven.

[Jake Halpern]

By early spring of 2008, Keith had robbed half a dozen banks and taken home about $60,000 in cash. And for a while, the authorities seemed clueless. But after the sixth robbery, a detective for the St. Louis County Police named John Bradley took notice. One thing that I learned about Bradley right away, this guy, he plays to win. He's a competitor. Well into his 30s and 40s, he played ice hockey. Played hard, too.

[Detective John Bradley]

Just being the type of detective I am, I'm confident that I will get him, and I hope I'm the one that gets them. I believe most cases can be solved.

[Jake Halpern]

Bradley responded to the scene of one of Keith's robberies at a Bank of America in Fenton, Missouri. One of the first things that he did was talk to the teller. Her name was Shannon. And she was shaken up, frightened by what had happened.

[Detective John Bradley]

It's a very emotional experience when something like this happens, when you're a victim of this, and that's who I believe is the victim. Of course, the bank is the victim, but it's just money. The tellers are the ones that are the true victims because they're the ones face to face with somebody not knowing how desperate this individual is and not knowing if this individual, for one reason or another, would suddenly become violent and hurt them.

[Jake Halpern]

Shannon shared a detailed account of what unfolded that day. She said the man reached out his hand and gave her a note that read, empty all the money out of the top and bottom drawers. She noticed that he had thick fingers, dirt packed under the nails, and what seemed like a freshly dyed beard.

[Detective John Bradley]

She could see that he was very nervous. He was trembling. That's a bad sign, you know, because when you have a suspect that is nervous, he's unsettled. That can lead to violence quickly.

[Jake Halpern]

In some ways, it was an odd combination of facts. On the one hand, the robber seemed to be a savvy operator who knew all the right things to ask and say. On the other hand, he seemed wildly nervous and slightly unkempt, with his dirty fingernails and poorly dyed beard. When Bradley examined the surveillance video from the heist he was struck by one detail in particular. After the robber handed over the demand note, he tucked his hand into the middle of his jacket, almost the way you'd see in those old Napoleon portraits, and he just left his hand there.

[Detective John Bradley]

And by doing that, you're implying or indicating that you have a weapon, you just are not displaying it. My thought was, well, if he wants you to believe he has one, he probably has one.

[Jake Halpern]

How worried are you that that's gonna go sideways and result in actual violence?

[Detective John Bradley]

Very worried. I mean, you have so many things that can go wrong that result in tragedy.

[Jake Halpern]

All of which made Detective Bradley think that now more than ever, he needed to drill down and find the man who was robbing all of these banks.

[Detective John Bradley]

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[Detective John Bradley]

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[Jake Halpern]

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[Jake Halpern]

Detective John Bradley started digging through recent St. Louis bank robbery reports, looking for any details that might connect them. He also starts talking to other agencies, sharing info, and eventually a pattern emerges. There are a bunch of heists where the robber is a bearded middle aged white man with glasses who uses a demand note. He always asks the teller to empty both drawers. And typically he wore a hat, either a baseball cap, a bucket hat, or what Detective Bradley called a boonie hat. Can you just describe to a Connecticut Yankee what a boonie hat is?

[Detective John Bradley]

Yeah, it's like a hat you would wear to go fishing. It's like a brimmed hat, you know, lures and things attached to the hat. Something that blocks the sun, kind of blocks your identity.

[Jake Halpern]

Detective Bradley became convinced that he was dealing with a serial bank robber. Two weeks later, there was a similar robbery in the same county. This time the robber walked away with almost $10,000 in cash. Afterward, a local paper ran the headline the Boonie Hat Bandit blamed for seven Heists. And that nickname, the Boonie Hat Bandit, quickly caught on, turning this mysterious figure into a folk villain.

[Detective John Bradley]

I mean, if you think about the type of person that can walk into a bank, threaten somebody and take money and walk out and then do it again and again and again, that's a very confident bank robber.

[Jake Halpern]

And what do you, what do you read into that?

[Detective John Bradley]

Somebody that probably isn't going to stop until he gets caught and hopefully he gets caught before somebody gets hurt.

[Jake Halpern]

The problem was this guy really seemed to know what he was doing. He had eluded the authorities pretty masterfully. Each time he'd exit the bank, loot in hand and melt back into the suburbs. Just another 40 something white guy with a dad bod driving through a vast, mind numbing expanse of Best Buys and Panera Breads. Throughout the fall of 2007 and into the spring of 2008, Keith continued robbing banks. He did it about once a month. Sometimes the payoff was a lot bigger than others. But on average, each of these robberies earned him about $10,000. And I really wondered how he just went home and slipped into the role of being dad. Did you find it difficult at all to look your daughters in the eye while this was happening?

[Keith Giamanco]

I wasn't very good at looking anyone in the eye at that point. It's hard to look anybody in the eye whenever you have this type of thing going on, this dark secret that you can only share with yourself. You can't share anything like that with someone else. If you do, you're had.

[Jake Halpern]

This made sense to me that he wouldn't be able to look his own kids in the eye. But what I still couldn't fathom was how did he allow himself to get to this point in the first place?

[Keith Giamanco]

I felt such desperation. I felt it was what I had to do. And I know that's gotta be very, very difficult for people to understand.

[Jake Halpern]

Yeah, it is.

[Keith Giamanco]

And I really don't know what to say to that because at the time it's what I felt like I had

[Jake Halpern]

to do at the time. Did it seem like a crazy idea?

[Keith Giamanco]

Yeah, it seemed very crazy, but also I felt a sense of being so desperate that I felt it was the quickest, easiest way out.

[Jake Halpern]

Did you allow yourself to think about how it could go wrong and what that might look like?

[Keith Giamanco]

No, I didn't want to manifest that. I was trying to manifest success. I know it sounds simplistic, but that's the truth.

[Jake Halpern]

It may sound simplistic, but this whole idea of manifesting it was very much in vogue at the time. There was a wildly popular self help book published the year before called the Secret. Keith had read it and embraced its philosophy. The book boldly proclaimed what you think you create, what you feel you attract, what you imagine you become. In many ways, it's a classically American sentiment. What Keith imagined, as far as I can tell, was continuity. The same house, the same school for his kids. The same version of himself. Mild mannered, self employed, holding it all together in his mind. Protecting that life required only a brief deviation. 10 minutes of controlled risk executed through the system that he built.

[Keith Giamanco]

It all seemed very surreal, but the whole process at that point got straight back to business of, okay, I need to deposit this money, write out checks, and then I got to go pick up the girls from school and then I have to mow the grass, you know, so just get back to life at normal.

[Jake Halpern]

Like literally life is normal. That was your checklist. Like, yeah, rob bank, pick up girls at school, mo grass.

[Keith Giamanco]

Yeah, that's pretty much what what it was.

[Jake Halpern]

Were you anxious about it?

[Keith Giamanco]

Once I watched the news, I knew I wasn't going to get caught.

[Jake Halpern]

Even with the money that he made, robbing a bank about once a month, Keith came up short. He fell behind on the mortgage and he was in danger of losing the house, the one he'd raised his kids in the bank, gave him a date. Pay up or they'd foreclose. So, on the day of the deadline, May 5, 2008, he robs yet another bank in Chesterfield, Missouri. It goes smoothly, no problems at all. The teller puts the cash in the envelope, and Keith walks out the door. Keith, by the way, never counted his money until he got home. And when he did, this time, he saw it was just 3,000 bucks, which he says is not enough to pay what he owes the mortgage company. So he makes a really bold decision. He decides to rob another bank that same day, just a few hours later. Was there any concern that you had that robbing the second bank would put you in additional risk if you did it in the same day?

[Keith Giamanco]

No.

[Podcast Host / Narrator]

Oh.

[Keith Giamanco]

In fact, just the opposite.

[Jake Halpern]

What do you. I'm not sure I follow.

[Keith Giamanco]

Meaning if you had never robbed two banks and went on a one day spree, my feeling was is that it would be least expected to happen.

[Jake Halpern]

Hmm. And his plan, it gets even bolder. He decides to rob a branch of bank of America in St. Peters, Missouri, that he'd already robbed five months prior. So he was going back to the scene of a previous crime. It almost seemed like he was daring them to recognize him. But the crazy part is, it works. Keith walks in, does his whole routine, hands the teller a note demanding payment, telling her to empty both drawers, and he walks out with nearly $11,000. Keith nets about $14,000 total that day, which is more than enough to cover his mortgage payments. And so, cash in hand, he races to his own bank so he can get a cashier's check and pay off his mortgage company in time so he doesn't lose his house. He arrives at his own bank, not as the boonie hat bandit, but as Keith Giamanco, smiling, easygoing, single dad of two. All very normal, except for the fact that he was carrying a burgundy leather briefcase with $14,000 worth of freshly stolen bills. As breezily as he can, Keith explains to the bank teller that he needs a cashier's check. She hesitates, like she's not sure about this request. Then the teller calls over the bank manager. And now Keith feels a flicker of worry, like this might not be good. The manager looks over the teller's shoulder, studying the computer screen, then lifts her eyes to Keith.

[Keith Giamanco]

She said, maya, it looks like you've been making a lot of cash deposits lately. I needed to think quick with an answer, which was, I was gathering money to save our home from foreclosure. Which was an honest Answer now by omission. There's a lot of dishonesty there. Correct?

[Jake Halpern]

Yeah. That you had robbed two banks earlier that day.

[Keith Giamanco]

Yeah, absolutely.

[Jake Halpern]

Yeah.

[Keith Giamanco]

But the answer itself, on face value, was honest. And that's why it came so quickly as just tell the truth.

[Jake Halpern]

In the end, the manager signed off on the whole thing. Keith got his cashier's check, paid off the mortgage, and headed home. Just another day in the double life of Keith Giamanco. I was struck by what Keith said, how helpful it was to tell the truth in this moment. Lies and the truth have a strange relationship with one another. In order to lie well, you need to adhere to the truth as much as possible with a kind of rigid discipline. You need to back the lies into the corners or the gaps. Keith told me that he had an end goal of $140,000 and that once he hit this, it would be enough to pay off his debts and then he'd quit. Spoken like a true gambler. I'm always skeptical when gamblers tell me this kind of thing. It feels like a line, something you tell yourself to reassure yourself that you have a plan governed by logic and that you are in control. There's a lot of deception in this story. Keith, he deceived a lot of people through his lies of omission, as he put it. His neighbors, his friends, his kids. But his story kept on reminding me that the most dangerous lies are always the ones we tell ourselves. Next time on deep cover.

[Detective John Bradley]

My partner and I at the time, you know, we would go out during different times and just kind of ride the area. That day, I think we were out already when the call came out.

[Keith Giamanco]

It was an all out onslaught of police cars, helicopters, cars in front of me, cars behind me blocked in, weapons dropped.

[Sophia Donner]

I just was angry at the living of a double life because that's what he was doing. There's the boony hat bandit and there's keechybanko.

[Jake Halpern]

Deep cover. The family man was produced by Isaac Carter and Amy Gaines McQuade. Our show is edited by Karen Shakurji. Our executive producer is Jacob Smith. Sound design by Jake Gorski. Original scoring and our theme were composed by Luis Guerra. Our show art was designed by Sean Carney. Fact checking by Annika Robbins. Our story consultant was James Foreman Jr. Special thanks to Daphne Chen, Sonja Gerwitt Morgan. Morgan Ratner, Kira Posey, Jake Flanagan, Corinne Gilliard Fisher, Eric Sandler, Christina Sullivan, and Greta Cohn. I'm Jake Halpern. Sam,

[Sponsor Voice / Advertiser]

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[Sophia Donner]

This is Sophia Donner from OK STORYTIME this summer. Find your next obsession on Prime Video and listen. We're not saying you need another obsession, but there could be a lot worse ones. Steamy romance, addictive love stories, and the book to screen favorites you've already read twice, so why not watch them a third time? Off campus? L the Love Hypothesis and more Slow Burn Second Chances Chemistry you can feel through the screen, and it makes you wish you were actually in that movie. We've got binge worthy series can't miss movies perfect for when you're ignoring your own problems or procrastinating as one does. Your next obsession is waiting. Watch only on Prime. This is an Iheart podcast. Guaranteed human.