Dangerous Ground: My Friendship with a Serial Killer

JULIE WINNINGHAM EXPLAINED TO JESPERSON THAT IF SHE WOUND UP behind bars, it was up to him to come up with bail money. The least he could do. As they discussed this while driving away from Julie’s mother’s house, Jesperson looked Julie in the eye and said, “I have an idea how to keep you from going to jail.” They were traveling east on Highway 14, just outside Portland, not far from where it had all begun five years before with Taunja Bennett.

“I need you to keep me from jail,” Julie reiterated. “You will have to bail me out.”

As he drove, Jesperson’s thoughts wandered into an unforgiving litany: Bail money! She expects me to bail her out. They all want something from me.

“The only way I knew how to keep Julie from jail was to kill her,” he told me, smiling, as if his plan was clever and humorous.

“You always promised to keep me out of jail,” Julie pleaded. “You need to follow through with that.” As she spoke, Jesperson drove, picturing himself taking Julie by the neck, staring into her eyes and watching her die, telling himself she was nothing more than a “leech” and “money pit.” In searching for the right reason, Happy Face had found a purpose and motive to take another life.

“I used my hands to strangle her,” he explained, before uttering that common phrase, “and put her out of her misery—or my misery, I guess is the way I looked at it.”

On my computer screen, inside the confines of my office, this crazy son of a bitch described killing Julie Winningham as if it were another day in the life of an over-the-road long-haul trucker. Here he was, twenty years later, laughing about it.

After deciding he’d had enough of Julie, Jesperson pulled over. He could not recall exactly where. He grabbed her in a fit of rage, took her into the back of his sleeper cab (just as he’d pictured moments before), and, without uttering a word, placed his hands around her neck and squeezed. She fought back. Her arms flailed. Her legs thrashed. Mucus came out of her nose and mouth as she gasped for air. A small woman of five feet four inches, 120 pounds, Julie Winningham was no match for an experienced serial killer. It took five minutes. Jesperson said he never broke a sweat, adding, “She would not have to worry about court any longer.”

*

SOME MEMORIES ARE SEARED into my brain with eidetic clarity. When I go to that place, I see those recollections completely and entirely. I hear those involved speaking. Perhaps it is the way I recall the incident, or how it really happened, but the memory is unchanging and unblemished. It feels genuine.

By the spring of 1994, my first wife and I took Mark and Diane to family court and won custody of their kids. They were in no condition to raise children. The tipping point was when I found my six-year-old nephew playing on the side of a busy road near their apartment at midnight. He wore only underpants and a T-shirt. He was alone. My brother and Diane, along with several transients who were forever coming and going and sleeping at their apartment, were upstairs, passed out. Empty bottles and cans, dirty laundry, dishes piled all over, and drug paraphernalia filled their living space. The smell of stale crack cocaine, booze, and cigarette butts was absorbed into the curtains and linens. No one in the apartment had any idea my nephew had wandered off.

Scheduled visitations, at our discretion, were set up after we were awarded custody. If we believed Mark or Diane were under the influence, we had the right to deny a visit. So many times they’d take the kids on Friday and not bring them back per the state’s order on Sunday night. We’d have to call child services and the police, or I would go out and track them down myself, engage in a confrontation, and haul the kids back to my home. By now, they’d been kicked out of that apartment and were living in motels and moving around a lot, deeply ensconced in their addictions. We thought the kids being taken away would have been a bottom, but it became, instead, a glass ceiling. We argued with Diane every time my wife and I ran into her. Diane was vulgar. She could be nasty and hurtful. I know at this time she hated us.

One Friday, they showed up and my brother was drunk. Diane had driven and seemed, for the most part, somewhat with it. My niece, Meranda, was in the backseat.

“You’re not taking the kids. Come back when you’re both sober.” Diane stood at my front door. She was not allowed on the property. Just ringing the bell was a violation of our agreement with the court.

“You need to leave, Diane.”

I cannot tell you exactly what she said in response because the memory becomes blurry here. I’m sure her rage included a multitude of the usual obscenities and threats: I can easily have you killed.... You’re going to pay for this.... Your brother knows people who can have your legs broken.

Diane was upset because we wouldn’t allow her into the house to see the kids. After a time, she calmed down. I then escorted her to the end of the driveway, where her car was parked, and my brother, now awake, stared at me, shaking his head. “You’re an asshole, you know that,” Mark said.

“Just leave, man. Come on. Show up sober. That’s all you have to do.”

As we approached the end of the driveway, Diane looked inside my recycling bin sitting on the lawn. Stopping, lifting her eyes away from the bin, she stared at me without saying anything at first. Then: “Take a look at yourself! You’re not so fucking different than me and Mark,” she said, kicking the bin as she got into the car.

“Just leave,” I said. “Get out of here.”

I watched them drive away. Walking back to the house, passing the bin, I stopped and stared at the contents: Bitch doesn’t know anything about me.

Yet, here’s the thing about Diane: she did know.

It’s easy to deny your own problems or even consider they exist when you focus on someone else’s. Inside my recycling bin were several empty twelve-pack Bud Light cartons, wine, and vodka bottles. What Diane articulated in a moment of clarity and observation while standing at the end of my driveway was that I’d taken them to court, won custody of their children, but all I’d done was remove the children from one dysfunctional home and place them into another. Diane could be perceptive at times; she understood life; she knew what suffering and growing up struggling was. She comprehended the idea that your adult self is a product of your familial DNA—this was what she’d tried to say.

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