When you read the pen pal bio of Christopher Endicott, you get the impression of a laid-back, outdoorsy 29-year-old looking for a connection. He describes himself as “an open book,” reflecting on past mistakes and saying he’s just hoping to pass the time with someone who’ll listen.
What you won’t find in that bio? That he murdered the relatives who took him in. While they were sleeping. At the age of 15.
Christopher Endicott is currently incarcerated at the Kentucky State Penitentiary for the 2011 double murder of Barbara and Gary Holloway, his legal guardians and second cousins. Their crime? Providing him with a home after his parents proved unable to raise him.
Let’s break down the case, the cover-up, and the curated image he’s presenting now.
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Barbara and Gary Holloway’s Murder – Crime Scene and Evidence Trail
On March 22, 2011, police were called to a home in Edmonton, Kentucky, after relatives discovered Gary and Barbara Holloway shot to death in their bed. Authorities quickly realized that their 15-year-old ward, Christopher Endicott, and a 12-year-old girl he was dating, were missing, along with the couple’s Chevy Lumina.
An AMBER Alert was issued that day, initially framing the teens as “possibly in danger.” But as police pieced together the crime scene, mpty shell casings, a stolen rifle, and evidence of a planned escape, that narrative unraveled fast.
The girl’s parents had reported her missing earlier that morning, and investigators discovered that she had been forbidden from seeing Christopher. The Holloways had grounded him over the relationship and even took his phone to stop them from communicating.
Later that night, a firefighter spotted the stolen vehicle. After a short chase and foot pursuit, Christopher and the girl were arrested. Police found the murder weapon abandoned, and also found $1,000 in cash that was missing from the Holloways’ home. Even the couple’s dog had been dropped off at a local adult daycare, possibly the only sign of compassion shown during the ordeal.
The Motive? Rebellion, Control, and a Forbidden Relationship
Though no official motive was released at trial, investigators and family members pointed to one clear conflict: Christopher’s relationship with the 12-year-old girl. The Holloways, along with the girl’s parents, had tried to keep them apart.
The theory? When Christopher couldn’t get his way, he snapped.
The murders were chillingly premeditated. Christopher used the couple’s own hunting rifle, which he loaded using hidden ammunition. He then shot Gary Holloway multiple times and Barbara Holloway once in the head while they slept.
Family members say there was no history of violence or abuse, just strict boundaries and an effort to provide structure. They had taken him in when his father was incarcerated and his mother was deemed unreliable. For the Holloways, it was an act of love. For Christopher, it was apparently something else entirely.
Christopher Endicott Arrest, Trial, and Plea Deal
Christopher was charged with murder, robbery, tampering with physical evidence, and fleeing police. Initially held at a juvenile detention center, prosecutors successfully argued to have him tried as an adult, citing the violent nature of the crime and his age.
At trial, his defense team cited his youth and sought probation, but prosecutors pushed for life without parole. The final sentence, however, was a 20-year prison term under a plea deal. The judge noted the potential for reevaluation at age 18, and parole eligibility begins March 2028, with an expected release in September 2030.
There have been no known appeals filed, and it appears that Endicott plans to serve out his sentence.
A Bio So Sweet… a Backstory So Chilling
Now in his late twenties, Christopher Endicott is once again trying to rewrite his narrative, this time through a pen pal bio on WriteAPrisoner.com.
I was young and dumb and made a choice that affected a lot of people’s lives. But you can’t change the past, only move forward and learn from it.
He describes himself as “easygoing” and “an open book,” and says he loves music, working out, and the outdoors. He talks about wanting to “move forward” and “become a better person.”
What he doesn’t say?
- That the lives he “affected” were two people who were shot in their sleep.
- That he tried to flee across the state afterward.
- That his relationship may have sparked the entire crime.
Even the wording of the bio raises eyebrows. The phrasing, “you can’t judge a book by its cover,” feels prewritten, polished in a way that rings oddly hollow for someone convicted of such a calculated crime. The absence of remorse is subtle, but it’s there.
The Reality Behind the Rebrand
Barbara and Gary Holloway weren’t just legal guardians, they were family. They stepped in when Christopher had nowhere else to go. According to relatives, they “gave him everything,” even after multiple school suspensions and behavioral issues.
In return, they were gunned down in their home.
The entire crime unfolded over the course of one morning, and ended with a boy trying to run off into the night with a girl whose parents were also trying to protect her.
While his bio paints him as mature and reflective, there’s no mention of the victims. No detail about what he did. No context. Just vague regret and a bid for companionship.
Final Thoughts on the Christopher Endicott Case
Christopher Endicott wants you to see him as someone who made a teenage mistake. Someone who’s learned. Someone who’s worth writing to.
But the truth? He made a choice that ended two lives. A choice that was cold, premeditated, and irreversible.
And now, more than a decade later, he’s telling a story that skips the ugliest parts.
As always, at Prison Bio Breakdown, we’re here to look past the penpal charm and into the truth. The bios may be sweet, but the crimes are anything but.
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