The Journey of Jeremy Gilmore: From a Good Upbringing to Life Lessons in Prison

From Small Town to Federal Prison

When I talked with Jeremy Gilmore on the podcast, one thing struck me right away. Here’s a guy from Aurora, Missouri, who grew up hunting and fishing, working at his family’s furniture store, even learning to fly planes at the local airport. Nothing in his background screamed “federal prison.” But that’s exactly where Jeremy and I ended up serving time together at Leavenworth.

Jeremy’s early years sound like something out of rural Missouri. “I always did a lot of hunting fishing,” he told me. “So on the weekends and stuff, I’d always have a gun in my truck and cruising the back road shooting coyotes or whatever and going to the ponds and fishing all the time.” He dropped out of high school in 10th grade to work at his cousin’s furniture store, doing deliveries once he turned 16. The family also ran the airport in Aurora, where Jeremy started working on his pilot’s license.

“I could get the plane up in the air. Could you land it?” I asked him. “Yeah,” he said simply. That’s Jeremy. Direct, no frills.

By 17 or 18, Jeremy’s path took a sharp turn when he started running around with a different crowd. They introduced him to meth. “I started using it. And so I had to stay up, you know, a couple of days at a time, I thought that was great,” Jeremy explained. “So I just started hanging out with more and more of them and quit doing the things I like to do.”

The Setup That Changed Everything

Jeremy’s first brush with law enforcement reads like something you’d call unbelievable if you saw it in a movie. A drug dealer he’d been buying from called him one night asking him to come over and sell back some of the drugs Jeremy had just purchased. When Jeremy showed up, there was a girl there he didn’t recognize.

“I ended up selling him back the drug that I bought off of him earlier. And she was undercover cop,” Jeremy told me. “So it was a whole, it was just a whole setup.”

That arrest led to a five-year suspended sentence with probation. Jeremy walked clean for four and a half years of that five-year term. Then competition from a local cop who also ran a taxidermy business changed everything.

Jeremy had learned taxidermy at schools in Missouri, spending nearly a year with an instructor learning the trade. He’d built up a legitimate business in Aurora with a big showroom displaying 70 or 80 mounted animals. But apparently having a deer in velvet, a river otter, and some deer horns without proper tags was enough to violate his probation.

“I was out there on the farm working on the farm,” Jeremy said, describing the day law enforcement raided his shop. “And my dad called me and said, hey, what’s all the cops doing at your shop? I said, I don’t know. And he goes, well, they’re all down there. You need to go check it out. So I left, I got off the combine and got my truck and went down to my shop. And soon as I got there, they arrested me.”

They took 90% of everything in his shop and put the story on the front page of the local paper for three weeks straight. Jeremy bonded out for $150, but the violation sent him to state prison for a year and a half.

Building a New Life

After state prison, Jeremy moved to Kansas City with his uncle who owned a cabinet shop. That’s where he discovered the Christmas light business. Starting with borrowed ladders and a buddy who wanted help, Jeremy eventually bought his own equipment and made simple flyers advertising “Santa’s L” services.

“I made a thing said, Santa’s L, hang your Christmas lights with my phone number on it. And I just drove around town, just sticking them everywhere,” he explained. The business took off. Jeremy would work union carpentry jobs during the summer, then take voluntary layoffs in the winter to focus on Christmas lights because the money was better.

Everything was going well until Jeremy ran across someone at his union job who was using meth. “I just started using again,” he said. “Then he had helped me hang Christmas lights and we would just stay up, just put Christmas lights on and do math all the time.”

The Federal Conspiracy Trap

What happened next shows how the federal conspiracy laws can destroy someone who’s essentially just a drug user. Jeremy was driving an H2 Hummer, which apparently made him look like a bigger player than he was. He’d drive his drug-using friend from Kansas City to St. Joe to buy drugs, sometimes crossing into Kansas when the St. Joe dealers didn’t have product.

“So they got my vehicle and we drove across state lines to Kansas. And I’d buy my drugs and they’d buy theirs and I’d bring them back to St. Joe,” Jeremy explained. When his associates got caught, they started naming names to get better deals for themselves.

“But I never got caught with nothing, never in anything,” Jeremy told me. “I couldn’t believe it. I’m like, there ain’t no way they can do anything to me. Cause I’m like, and I never, I never got caught with nothing or anything. So how can you charge me for something I didn’t do?”

Jeremy’s first federal attorney had to drop his case because of a conflict with another client in the same conspiracy. His second attorney was fresh out of law school, more familiar with divorce cases than federal drug conspiracies. She was honest about the impossible situation: “You could go to trial, get 10 years or plead and get 10 years.”

Jeremy chose trial. After two weeks of testimony from cooperating witnesses, the jury found him guilty. “There was probably two or three of them that I never even seen before that testified on me,” he said.

Life Sentence for a User

What came next still takes my breath away. At sentencing, Jeremy’s family hired new lawyers from California. But when it was time for the defense to speak, the judge told Jeremy’s original lawyer he was stupid. Then came the hammer: a life sentence.

“They ended up sending me to a life sentence,” Jeremy said. “They eight fifty one me on everything that they could.” The 851 enhancement used his prior convictions to increase his sentence, and going to trial instead of cooperating meant losing any chance at a reduction.

“I was like, man, how am I going to do it?” Jeremy told me when I asked what went through his head hearing “life sentence.” That question would define the next several years as he fought his case through appeals while navigating the federal prison system.

Jeremy’s story shows how someone can go from hanging Christmas lights in Kansas City to serving a life sentence in federal prison, all without ever being caught with drugs. It’s a reminder that the federal conspiracy laws cast a wide net, and sometimes people who are really just users get swept up and treated like kingpins. Jeremy eventually got his sentence reduced through a successful appeal, which is how we ended up serving time together at Leavenworth. But that’s a conversation for another day.