Happy Face

And so James, he gets to the front door, he puts his key into the lock, he unlocks it, and with a sledgehammer in one hand, he attempts to push the door open. And so James, as he's pressing the door barely open, he's staring into this crack, trying to make out what's going on inside of his house, and then suddenly a set of eyes meet his from behind the door.
And before James can do anything, this man that is standing inside of his house says to James, Hey there, I'm Mr. Bollin.
And what you just experienced is just a taste of what you can expect when you listen to the Mr. Bollin podcast.
In every episode, I peel back the layers of the strange, the dark, and the mysterious. From unexplained phenomena that challenge everything you thought you knew about reality, to true crimes that keep you up at night, I cover it all.
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Previously on Happy Face.

After the second murder, the Happy Face Keller says,

he realized he liked what he was doing. This triggered something in me, he says.
It was getting easy. Real easy.
He started killing in 1990, and he stopped in 95. The five years is not an isolated event, it was an escalation.
I think he was groomed to be who he is. Keith's father, Les, was a very resourceful, ingenious man, but he could be a monster.
He was horrible. I hated him.
He dragged me to a nursing home to visit one of his hunting buddies. He said, my friend Smitty's not doing too good with his lung cancer, Keith.
Talk to him, son. Nobody likes to die alone.

I never feared a dead person after that.

One of the few people that Keith opened up to about his childhood was psychologist Al Carlyle.

So even by the age of eight, there was a lot of anger.

I went back to my truck and rehearsed the lies I planned to tell when I was arrested. What made me cross the line into murder.

Maybe it was my nature.

In the pines, in the pines, where the sun don't ever shine,

I would shiver the whole night through. The psychologist Al Carlyle interviewed a number of the most notorious serial killers.
Ted Bundy, Arthur Gary Bishop,

Wesley Allen Dodd.

But he had a particular fascination

with Keith Hunter Jesperson.

Here's his writing partner,

Carrie Ann Keller, explaining why.

Keith told Al he was always

100% reality when he killed.

He was not in fantasies.

Keith said to Al, and this was a really honest observation that gave Al some really good understanding. Fantasies are left to the times when we are alone to ponder over what we had done and what we wish we could have done.
It was a different type of, I mean, Ted Bundy would drink alcohol to be able to do it, you know, every time. So he was blurred a little bit.
Keith didn't have to be drunk. He remembers 100%.
He is there 100%. There was not a real anger.
It was like I was taking care of business. Okay.
It was like a mindset. You just put yourself in this mindset that you're doing a job, and that's the way it is.
And that's why I think like Bundy and then when they say well this entity stepped out and did this what it is is not an entity it's actually they're trying to cast the blame off to something else and say well I'm really a nice guy it was that evil side of me that did this and I'm just saying I did it I was in full control of my emotions I knew what I was doing you know dreamlike stay no I were basically the same I'm the same person I knew right and wrong I knew everything I was like it wasn't into the twilight zone like the one that I dragged into the truck there I said I after I killed her I went to McDonald's I sat down I bought I bought myself a meal I bought her a meal and I came back out in the truck and I said it right there in front of her she's dead and then after I done I ate I ate her meal I said see if you wouldn't have got me off looking mad here you could have ate something here what was it a way of part of your mind pretending that they were still alive, like you didn't want to kill them? Well, I don't know if that's the case. That's where you come in.
For so much of our story, the Happy Face Killer has existed almost as a specter, a background entity that looms over everything. We know about Keith's childhood, his wife and family, and we've heard from his victims' families.
We talk about Keith almost in passing, like a boogeyman. But the fact is, he's real.
He is a serial killer. and as Melissa works to distance herself from Keith's legacy,

we wanted insight into the psychopathy that drives him, and to hear about it in his own

words. I'm Lauren Bright Pacheco, and this is Happy Face.

One of the things that's so jarring about Keith is that he comes across as almost earnest at times,

like he honestly wants to be helpful.

Here's Keith again, talking to Al Carlyle.

Well, I hope this is what I'm giving you is helping you.

It is.

Thank you. It is.
It is. Because I've always been very direct, I think.
And a lot of people can't understand why I want to be direct. They think I should, like the biggest consensus in this prison, they say, well, you're talking to a psychologist, or I'm talking to a movie deal, or I'm talking to this.
He says, well, are they paying you? And I says, no, no, not. And he said, well, I wouldn't tell them anything.
And I said, well, then how do you get the truth out? I mean, does it have to have a price tag to it? I mean, that's why interviews with convicts, they put a price tag, well, we're going to pay you $50,000. It taints the truth.
And I look at it this way, that I fucked up. I did.
I mean, I know I did. I threw my life away, pretty much, except for a prison life.
And you can have a good life in prison, but I look at it as if the truth means, if it hurts, well, so what? You know, at least anything I can do to make people understand. It isn't just strangers and journalists who could be under Keith's spell.
Melissa, too, used to feel it. His air of certainty definitely played a part in other people believing in him and why probably his victims believed in him and trusted him over their own voices.
And that's something that's been very difficult for me is trusting my own intuition when someone seems to have the answers and seems to know with certainty where things are going. And if I don't feel right about it, to trust myself over the appearance of confidence.
And that's something that's been difficult to navigate. But my dad was very much that.
He exuded confidence and certainty. And whatever he said was truth.
And you can rely upon it and you can trust it. But not really.
It was Phil Stamford, crime reporter for The Oregonian, who first coined the name Happy Face. Almost playful, almost a little too disarming for the monster behind the symbol.
A lot of people ask me, how did your dad get the name the Happy Face serial killer? And I believe it came after your series of articles, and maybe could explain that to me. Well, yeah, I guess you could say I named him in those articles, but in another sense, he named himself by putting a little happy face on that letter.
I mean, that's strange stuff. Someone confessing to five murders and a little happy face, which is have a nice day.
There's a serious disjuncture in a personality like that. But the reason it stuck, the reason it was a good nickname is that it was really true.
There was something about it. The killer who signed his letters with a happy face.
Murders like this are fascinating because they're acts of compulsion. He didn't plan to do it.
There was nothing he could gain from it. He did it for reasons he didn't understand.
And that's, I guess, why serial killers who just kill for the sake of killing are so fascinating to us.

What struck me when I was sitting across from him in the Clark County Jail is here's this big, slightly, you know, dull, very slow-moving person who wasn't a threat to me.

He wouldn't be a threat to most people.

He was a threat to women who sort of triggered something in him. And when that happened, something else came out.
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You know, there's this quote that I've heard from Margaret Atwood, and she has said, Men are afraid that women will laugh at them.

Women are afraid that women will laugh at them.

Women are afraid that men will kill them.

That's our deepest fear.

And when I heard that quote, I thought, that sums up my dad.

You know, the greatest fear of women laughing,

when women laughed at my dad or rejected my dad.

Correct.

That's when he seemed to snap. Correct, because he didn't kill everybody he was with.
Not every woman. It was spread out a little bit, you know.
It was when someone hit that correct button. Whatever had come out of their mouth that shouldn't have in his fantasy or his reality.
That was the cutoff her well i listened to their the way they talked about life and the way they treated people you know sinnie rose i didn't give her a chance to talk that was just a brutal murder uh the other ones are with me for any given time as soon as they opened their mouth and they had other alternative motives behind it they acted like men were a piece of shit anywhere they need to be used and that's when they came up with that kind of a scenario i kind of like i had no no feelings for him i just threw my feelings to the wind that was kind of a trigger that was kind of i would say a kind of trigger was the fact that they had they thought that they were the ones uh controlling or that they were going to manipulate whoever they wanted to. They didn't give a shit of who it was.
And they were so arrogant when they talked. They didn't care that I heard about it.
They just figured I was so much interested in their body that I'd look past that. And despite the brutality of these crimes, a pattern emerged with several of the people we spoke

to, that Keith was quiet, cooperative, and in many ways came across as almost pleasant.

But ultimately, Keith was only concerned with getting attention for his crimes.

Here's Jim McNally, retired detective from the Multnomah County Sheriff's Department.

What do you remember hearing about Jesperson, my dad, before you met him? When did you actually meet him, and how did you size him up in person? The only interaction I had with your dad was when I talked to him in the penitentiary, and I found your dad to be pretty charming, actually. I learned the technique of just taking my fist, because when you hang on to something, your arms get, your hands get extremely tired, because the muscles are trying to push away, and you're fighting, the body is very resilient.
So you have to stay away from the muscle tissue, you have to go directly to the larynx, right in the vocal part. So I laid a fist like this, and I locked my elbow, and I just pushed down on it.
And with my elbow locked, I could just take away the time. I listened to her.
I smelled, I was waiting for the smell of urination. And I was just watching the time.
Like I was just waiting for my date, you know? In your opinion, what drove his need to confess? Guilt or attention? I think it's attention. And I say that because he just was so upfront with everything.
And when he was speaking to the sheriff from Iowa, he made his comment about getting ready to leave. Well, I know a lot about this stuff, and if you need any more help, come on back.
That seems pretty arrogant, though, that he's an expert. He wants attention.
That's what he wants. I played that back and forth in my mind for months, even especially when Detective Buckner in June of 95 went ahead and he exploited everyone and said, well, we think we have the happy-faced killer in prison, in county jail here, and I arrested him, you know, so to speak.
I knew the glory seekers were out there and they wanted to prove that I was this person, and I felt, well, why should they have the glory of provingah County Sheriff's Department. When did you actually meet my father, and what did you think when you saw him? I met him in the Clark County Jail, and this was after he was telling cellmates that he had killed someone in Molo Macanee, and there was nothing particularly unique about meeting him when I did meet him, because he was one of hundreds of inmates that I had gone into the jail to interview.
So I went to talk to your father with a very serious doubt about the accuracy of what he was claiming. And there was nothing particularly impressive about him or memorable.
I mean, he was a great big guy that was very calm and collected and was not macho and didn't swear and didn't use a lot of jail terminology because he hadn't been in jail a lot. There's a constant, even though I know the cops really don't know who I am, but I still have to think in the back of my mind that they're looking.
And I have to worry about what people see all the time, even though I know they don't see me as the murderer I am. They see me as a nice guy or someone that is just there.
I don't look out of the ordinary. I'm just like a normally guy, just doing my job and going on with business.
In my career, I worked with violent offenders on a regular basis. Your dad did not fit that profile in terms of his demeanor, in terms of his appearance, in terms of his vocabulary.
He was the farm boy next door, literally. I mean, if I had been a female and met him in a bar, I wouldn't have been particularly frightened because he had a very unassuming presence about him.
That's what I noticed, too, when I was around my dad and we would be around other females or in public. He seemed to be charismatic and people didn't seem intimidated even though he was so tall and so big.
And I think that might have been maybe to his advantage when he was finding his victims. Do you think he was really calculated in finding his victims or do you think he was more of an opportunist? Yeah, I wouldn't assume that he was particularly cunning in this whole thing.
I mean, he had a demeanor about him that was very mellow. I mean, so I wouldn't attribute his series of murders to being a particularly cunning person.
I would attribute it more to the fact that he didn't have any kind of a threatening demeanor about him. I mean, if he was your next door neighbor and you saw him every day mowing his front yard, you wouldn't be concerned about him being your next door neighbor.
And knowing my dad, he would offer to mow your lawn. That's what was so interesting about my dad.
He was generous and kind in so many ways, you know,

but then now looking back, it's very, very eerie.

There are some people that are down on their luck,

and they'd say, you know, I'm broke.

I don't have no money.

I said, that's all right.

I'll stop up here and we'll buy dinner and get the other end.

I hand them a $20 bill.

I said, here, grab a cab, go home or whatever,

where I take them right to their home.

I'd gotten lots of numbers from girls that I'd given rides, and guys I've given rides to.

Hey, when you're over here in town, we'll go party, we'll have a good time.

I put in kids on Greyhound buses and send them home to their mom and dad.

Paid for the ticket, just so that they'd get home safe. Keith spoke to Jack Olson in prison and lamented the fact that he wasn't going to see his children again and that he'd wished he'd moved back to Canada 30 years earlier.
Here's Stephen Booth, psychologist Al Carlyle's publisher. He had his freedom going out and driving the truck, but when he thought he was going to get what was rightfully his, a relationship, happiness, whatever, and he didn't get it, he didn't like that very much.
And it reminded him of all the traumas that he had as a kid, not necessarily at the hands of his father, but at the hands of everybody. It sounded like everybody was victimizing him.
I think with your father, he was feeling awful for himself. He doesn't really care about anybody else.
It sounds to me like he lacks the empathy that we've been talking about. And remorse, remorse to me is, gosh, I've done a bad thing.
I really need to make up for it. Why would he need to make up for it if he doesn't care what other people think? But he does care about himself.
I think he tried to kill himself because he didn't like the idea that he was the person that he'd become in his own mind. But that doesn't mean that he cared about the people that he killed.
Yeah, I was hating myself. I didn't like what I'd become.
And that's probably why I was so easy to convince myself to turn myself and get it over with. Now, if I hadn't have done that, that's why I think in some respect that why is it that so many killers get to a certain point and all of a sudden they just destroy themselves.
And what is the magic number? I always keep saying, well, eight is enough. Because if you look through history, and I'm sure you have, I bet you go through how many serial killers out there reached the number eight and stopped and basically got caught.
And there are a lot of them that got caught with number eight. Keith began to buy into his own mythology.
And in the end, the victims never mattered. It was Keith's world.
His need to confess was just another extension of his fragile and narcissistic ego. Here is retired detective Chris Peterson again.
He told me that guilt was a factor. I think it's more like he was now beginning to be in the limelight a lot, and I think he enjoyed it.
And that's why he started talking about this, simply because he knew that he was likely to go spend the rest of his life in prison anyway. So now this was an opportunity for him to get a lot of attention.
I think that was really what his motivation was. So do you think a lot of his mythology as this macho, tough, ladies' man killer, it's revisionist history that he's created? Yeah, he's never come across as a tough guy to me.
I mean, I still see him as kind of the big dumb farm boy. I mean,

that's the way he acts. And coming from a farming background, I'm not meaning farmers, but he came

across as just a kind of a hayseed. He's never exhibited a macho attitude in my presence.

It's always been more of a look at me, look at me, I'm somebody, you know, as opposed to

blustering and acting like a tough guy. He's never done that around me.
And how did his demeanor change? You mentioned that he even suggested you guys work on a book together. It wasn't really a book.
He wanted to, he suggested that he and I go on a tour and the tour was going to be, we will teach people how not to get murdered, which was, of course, laughable. But he said, why don't we go on a tour, and we can make a great presentation of this.
And I never shut him down on that idea. I just let him have his fantasies because that was the last thing I was going to do with a serial killer was take him on a tour.
So almost like a road trip media tour? Absolutely. Absolutely.
He wanted as much publicity as he could get, and that was what it was about. What personally bothers you about your interaction that you had with him to this day? I guess more than anything, what bothered me about him was just the fact that he wasn't really trying to hide it.
He was relishing the attention and in the number of homicides that I worked in my career, I didn't see that very often. Most people, once they were charged or convicted, they didn't feel particularly good about it.
He just seemed to continue to feel positive about his accomplishments. I'm at home in prison here.
I told, I had an interview here, out here with Channel 8 News one time, back in 97, they came in, they asked, it was like around Halloween, it was kind of comical. We're sitting there.
She said, well, I don't believe you killed us. I told the one detective, killed 166 people, and right after that they gave me this interview, and I told them how many of you killed.
I said, 166 people. No big deal.
And you could see the guy was kind of half trembling here. He was like, you were sitting there.
I'm not in leg irons. I'm not in handcuffs.
I'm sitting right across from you, and I'm looking right at him. I said, I'm at home here.
Now, I've killed all these people. Now, I could kill you here right now.
But you know the only reason why I'm not killing you right now? It's because I have a TV set in my house, and I get to keep it. And the only thing that your value is worth, a TV set.
That's another example of Keith's sick sense of humor on display. He did not kill 166 people, but that exaggeration takes away from the lives he did take.
Here's Melissa. It really used to bother me that when all these headlines would happen, like with my dad or with other infamous criminals, we would hear their name all the time and that the victims, you would hear just a couple words about the victims.
Like with Tanya Bennett, I heard that she was burned at her age, that she was mentally slow. Those were the adjectives I've heard.
I don't know anything about her life other than that. And it was easier for me to be desensitized in a way that she was a real human being because of that.
When I went on the quest to really learn about more of who Tanya Bennett was, I reached out to all of her family members. Michelle White was her sister, and I reached out to her and her brothers, and I met with Michelle White, and I sat down, and I got to look at pictures of Tanya, and she told me all about her sister, and I got to learn, you know, their relationship and how they got the news.
And it made this person that was just a name on a newspaper into actually a human being. And it made me realize the lives that my father really took.
That it's not something that you could kind of brush aside and pretend that it's not real now. If you're learning that these people existed in real life and that they had real lives and people that loved them and you get to learn about their childhood and growing up, then it makes them a real person.
Eight people, eight women, whose lives were ended by a monster with a wounded ego. A warning to the listener.

After each of the names follows Keith's thoughts about what he had done. Not to glorify his crimes, but to demonstrate just how little these lives meant to this psychopath.
These were his victims. Tanya Bennett, January 23rd, 1990, Portland, Oregon.
Raped, beaten beyond recognition, and strangled. It wasn't the power, though.
There was no power of being like, I'm domination, I'm this and this, but it felt like, you bitch. I mean, I could just think back to all the hostilities I've had against people, against women, for one thing, and have never pulled the trigger.
And here I pulled the trigger once, and I just kept pulling it. And I hit her until I opened my hands for a sword, and that's what stopped me.
It wasn't the fact that she's crying, and Mommy's making them stop, making them stop. It was the fact that my hands hurt.
Jane Doe, referred to as Claudia by Jesperson, found August 1992 in Blythe, California, raped and strangled. And then I got into this little game of a strang'd strangle her until she was just about dead,

and I'd pull her back out of it.

I did that probably a total of four times,

at least four times with her.

Cynthia Lynn Rose, found September 1992 in Turlock, California, strangled.

Some people die quicker than others, and she died right away. I thought maybe while I strangled, I might have broke her neck.
I'm not sure. But my intention was that I was just going to strangle her, then I'd take her down to a Y spot, and we'd have fun.
Or I'd have fun. But that didn't even come about.
Lori Ann Pentland, November 1992, in Salem, Oregon. Strangled.
She started talking about her life and how miserable it is and she can't make a living and she wished it all end. And I said, you know, I think I'm going to do it and I'm going to strangle you.
That's what I told her. She said, go for it.
And she said, go for it. She thought I was just kidding.
Jane Doe, referred to as Cindy by Jesperson, body found June 1993 in Santanella, California, strangled. I made the decision that if I should get her into my truck, she would be mine.
I had to get her in the truck on her own free will. I wanted her to make that conscious decision.
She had to want to come along with me. Jane Doe, referred to as Susan Ann by Jesperson, found September 1994 in Crestview, Florida, raped and strangled.
I told her, let's have some fun. And she says, I don't want to do it.

I felt, in a way, that because she was, like, so bossy,

telling me, well, I'm going to do this,

I felt, I'm going to tell you to do this, and you're going to do it.

She wouldn't submit to it.

And I said, well, fine.

I don't have to have this.

And I just killed her.

Angelisa Breeze, January 1995, Spokane, Washington. Raped and strangled, Jesperson later strapped her body to the undercarriage of his truck and dragged her for 12 miles to remove her face and fingerprints.
He's implied in a letter to Melissa that she may have been alive when he did so.

When you stopped and you took the body off and you saw what had been done, did it affect you at all? Did you feel anything? No. Because here's a gal you spent some time with.
And she was basically, all that was left of her was her legs, her ribcage was pretty much gone,

her intestinal tract was gone, her skull was ground in half, her fingers and arms, her upper arms were gone because I taped them like so so they'd grind off first. When I cut the ropes from underneath there and just dragged it down the hill, I mean, it was relatively nothing there.
Julianne Winningham, March 16, 1995, was Shugal, Washington. Raped, beaten, and strangled.
Jesperson's final victim, and the one that led to be with. But then when she's drunk, she was like being with my dad when my dad was drunk.

She reminded my father.

All the times he'd be out drinking, come in and everything was like, you got to do what I say.

And I just rebelled against it.

Yeah.

So I grabbed her and strangled her.

Strangled her until she was unconscious.

Then I taped her up. And I took her out of town because I was going to get rid of her body outside of town there.
I went up to the top of this hill up on top of Camas, or Washougal Hill going east on 14. I got up there, went down on the other side, and have sex with her again.
Only this time she's kind of like wanting to play act

so that make me feel better

that I would let her go, so to speak.

What did that do to you?

It was a turn on

because she wanted to actually enjoy

as it was all over with.

I said, there's no going back.

I told her, I said, there's no going back.

I've killed seven before you

and I'll kill you too. Jesperson would receive multiple life sentences for his crimes, but they'd leave his daughter, Melissa, emotionally imprisoned.
In two weeks after Thanksgiving break, Happy Face returns

to explore the residual impact of Keith's crimes on Melissa's marriage and family when the contents of his unopened letters forces her to face her deepest insecurities and fears. Happy Face is a production of HowStuffWorks.
Executive producers are Melissa Moore, Lauren Bright-Pacheco, Mangesh Hatikador, and Will Pearson. Supervising producer is Noel Brown.
Music by Claire Campbell, Paige Campbell, and Hope for a Golden Summer. Story editor is Matt Riddle.

Audio editing by Chandler Mays and Noel Brown.

Assistant editor is Taylor Chacoin.

Special thanks to Phil Stanford,

the publishers of the Oregonian newspaper, and the Carlisle family.