Jeffrey Trail Wiki: Who Was Andrew Cunanan’s First Victim?

What happened to Jeffrey Trail in 1997? How, and why, was he murdered? Who was he? And how did he know spree killer Andrew Cunanan? Our Jeffrey Trail wiki looks to answer these questions and more.

To his friends and family, Lt. Jeffrey Allen Trail was a simple, fun-loving, laid back, and caring human being. According to the people who knew him, he was the epitome of what a beloved and hardworking son, brother, friend, and co-worker should be. He cared deeply about the welfare and happiness of those who were closest to him, and he never faltered when it came to ensuring their well-being over his own.

Knowing all that, people are shocked when they learn about the tragic and gruesome way his life came to an abrupt end. How exactly did this sweet, unassuming young man with a seemingly bright future in the military get mixed up with the very troubled, obsessive, egomaniacal, and violent Andrew Cunanan?

Who Was Jeffrey Trail?

Jeffrey Trail was born in De Kalb, Illinois on February 25, 1969 to Stanley and Ann Trail. He was the youngest of five children and by all accounts, the family was extremely tight-knit.

He ran track, attended church, and loved planes, working at the airport as a teen.

His parents were very proud and supportive of their youngest son’s numerous achievements, including his enrollment in the United States Naval Academy.

Trail graduated from the academy in 1991. He was immediately stationed in San Diego, on the Navy Cruiser USS Gridley. It was at some point while he was in San Diego that Trail met Cunanan.

Trail was in the Navy for five years, serving in the Gulf War, before leaving in 1996.

Jeffrey Trail

Jeffrey Trail; Photo: www.findagrave.com

An Unsung Gay Rights Advocacy Trailblazer in the Military

As a well-respected naval lieutenant and Gulf War veteran who also happened to be gay, Trail demonstrated the same level of compassion and charisma around his fellow naval officers as he did in his personal relationships, despite never having divulged his sexuality to any of them.

In those days—the early to mid-1990s, to be exact—homosexuality was still a largely taboo subject not only in most branches of the military, but throughout society as a whole.

The military’s strict “Don’t Ask Don’t Tell” policy, which was punishable by permanent discharge, was in full effect. And Trail had a difficult time coming to terms with his own sexuality as it was, let alone allowing others to become privy to it.

While he legitimately feared his sexuality would jeopardize his military career, Trail was nonetheless a leading advocate of lifting the ban on homosexuals in the military, although nobody knew about it at the time.

During an anonymous 1993 interview hosted by Richard Schlesinger on the CBS show 48 Hours, Trail stated that his reasoning behind supporting the lift on the ban was that, “Gays are here in the military. We perform our jobs, we do it well.”

When Schlesinger asked about the potential effects of the ban being lifted, Trail gave an answer that was very telling about his character. His answer demonstrated that he wasn’t as concerned about the effect on his own life and career as he was about how it would impact the future of the United States Armed Forces and the strength of the national defense.

“The effect of the ban being lifted is you maintain a quality navy, you increase the quality of the navy by not removing homosexuals, and you also save money.”

He went on to say: “You’ve invested this money in homosexuals in the navy and you’re putting it to good use instead of throwing it away… There are—whether people like it or not—there are gays in the military. They’re very top-notch performers. They know what they’re doing.”

At that stage of his life, he hadn’t even told his parents that he was gay and had participated in same-sex romantic relationships. Like many gay men throughout the 1990s, Trail had a hard time accepting his homosexuality and was perpetually waiting for the “right time” to reveal it to his parents. Unfortunately, as fate would have it, he never got that opportunity.

In fact, the Trails found out about their son’s sexuality and secret life in the most horrifying way imaginable: after his calculated, cold, and bloody murder, which was splashed all over the media.

An Ill-Fated Friendship

Despite many vehement warnings from the few friends and family members who had met Cunanan, Trail continued his friendship with his future murderer, with the two being inseparable for a time.

Cunanan even began indulging Trail in a lavish lifestyle, purchasing expensive accessories, clothing, meals, and drinks for him and even setting him up with other male suitors.

Andrew Phillip Cunanan FBI

Andrew Phillip Cunanan (Photo: FBI)

Investigators believe that the two may have been romantically or sexually involved at some point. But friends of Trail say that is not the case.

Trail defended Cunanan’s character, no matter how many times others would call his odd behavior into question. When asked why he was such a fierce defender of Cunanan, Trail stated, “It’s kind of like having a black sheep in your family. You put up with him and you just love him.”

Little did Trail know that the seemingly simple and offbeat persona Cunanan spent his life artfully crafting and using to manipulate others would ultimately result in both of their demises.

Related: Andrew Cunanan: Cross-County Killing Spree Ends with Versace Slaying

From the very beginning of their friendship, it always seemed obvious to everyone, except Trail himself, that Cunanan was a volatile and phony master manipulator who had ulterior motives for everything he did, though those motives were never unveiled.

Over 20 years later, the fact remains that we may never know the exact reason behind his vicious cross-country killing spree, or what exactly sparked it. One thing is for sure: Cunanan displayed signs of a deep-rooted and emotionally unhealthy attachment to his first two victims, Jeffrey Trail and Cunanan’s one-time lover, David Madson.

The three men were mutual friends, but it was painfully obvious that Cunanan more than simply admired Trail. It seemed that he wanted to be Jeffrey Trail in every way imaginable.

In July 1997, Trail’s sister Lisa told The New York Times that Cunanan idolized her brother so much that he’d try to emulate a lot of his actions and mannerisms.

“When Jeff got a haircut, Andrew had to have the exact same haircut. When Jeff went to San Francisco and got a certain style of baseball cap, Andrew had to go to San Francisco and get the very same cap. When Jeff grew a goatee, Andrew grew a goatee,” she said.

Obsession Leads to Murder

If Cunanan’s behavior was actually as erratic as Lisa described in her interview, then it’s no wonder that it raised a lot of red flags among her brother’s circle of friends.

As the friendship progressed, it became evident that Trail was also growing tired of Cunanan’s compulsive ways, so he began distancing himself.

In 1996, after a brief stint as a trainee with the California Highway Patrol, Trail moved to Minneapolis, where he began a new job as a district manager for a propane company called Ferrellgas.

Madson was already living in Minneapolis. It’s said that Cunanan may have become suspicious or jealous of Trail and Madson’s relationship after his friend moved to the same city as his ex.

Upon Cunanan’s announcement that he was coming out to Minneapolis to visit him, Trail expressed grave trepidation to another sister, flat out stating that he didn’t want his friend to come at all.

That fateful visit would prove to be lethal for both Trail and Madson.

Cunanan’s Brutal First Kill

On April 29, 1997, Jeffrey Trail’s bloodied corpse was found in Madson’s Minneapolis apartment, with neither Madson nor Cunanan anywhere in sight.

The body was wrapped up inside a large carpet. Trail had been savagely beaten to death with a small hammer.

He was just 28 years old at the time of his death.

A few days later, Madson’s body was found on the shore of Rush Lake. He has been shot with the handgun Trail purchased during his training for the California Highway Patrol.

So the hunt was on for Andrew Cunanan. He was added to the FBI’s “Most Wanted” list in June of that year.

On July 23, 1997, after killing three more victims while on the run, including famed designer Gianni Versace, Cunanan committed suicide. He did not leave a note, so his true motives for murdering Trail, Madson, and his other victims can only be guessed at.

Related: Lee Miglin Wiki: Who Was This Andrew Cunanan Victim and How Did He Die?

Portrayal in “The Assassination of Gianni Versace”

Although there’s a great deal of uncertainty surrounding the exact details of Trail’s untimely death, season 2 of the FX series American Crime Story: The Assassination of Giovanni Versace attempted to fill in some of the unknown details.

The show sheds a new light on what might have happened to Jeffrey Trail in his final days, not long before the famous murder of internationally acclaimed fashion designer Gianni Versace.

Related: Gianni Versace’s Murder: Who Killed Gianni Versace?

It is important to note that this series puts forth a fictionalized version of Trail’s experience with Cunanan. With spree killer Cunanan ending his life and not leaving behind any confession or suicide note, all investigators and the media can do is theorize about what really happened to Jeffrey Trail.

But Trail’s life and death go far beyond theories and television. His family and friends miss him dearly.

“Jeff had a goodness to him, a sincerity you just can’t buy,” Trail’s sister Candace Parrott told People magazine. “Andrew took a lot away from us, but that is one thing he never will.”


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