Two Unsolved Florida Murders That Deserve Another Look

One happened less than two years ago. The other happened more than 35 years ago. Both families are still waiting for answers.

Florida has no shortage of cold and unsolved cases.

In April 2026, as Florida announced a new statewide cold-case initiative using advanced DNA testing and forensic genetic genealogy, state officials put the scale of the problem into perspective:

Florida has approximately 21,000 unsolved murder cases, around 2,500 unsolved missing-person cases, and nearly 900 cases involving unidentified human remains.

The state's unsolved homicide count stretches back to cases dating from 1965.

Those numbers are staggering.

But numbers have a way of becoming abstract.

Behind each one is a person. A family. And often someone who knows something.

Two cases recently brought to the attention of Florida Unsolved deserve another look.

One occurred in Central Florida in 2024.

The other happened here in St. Augustine in 1990.

Both remain unsolved.

Deqwan Markell Chester

Apopka — October 30, 2024

Deqwan Markell Chester was 19 years old.

Shortly after 2:00 a.m. on October 30, 2024, Orange County Sheriff's deputies responded to the area of West Celeste Street and South Washington Avenue in South Apopka after a reported shooting.

They found Chester suffering from gunshot wounds.

He was pronounced dead at the scene.

The location was reportedly less than a block from his home.

And there may be a remarkably narrow window in which to understand what happened.

According to Chester's aunt, speaking to WESH shortly after the killing, the family's understanding was that Deqwan arrived home, unlocked the door, and entered the house at approximately 1:50 a.m.

At approximately 2:01 a.m., a friend was reportedly knocking at the door.

Eleven minutes.

A neighbor reportedly heard multiple gunshots but did not see or hear a vehicle speeding away.

Chester's family developed a theory: someone may have contacted him and induced him to come back outside.

His aunt believed that, if that happened, Deqwan likely knew the person.

That is a family theory — not an established investigative finding.

But it raises obvious questions.

Who communicated with Deqwan during those eleven minutes?

What do his phone records show?

Were there text messages, calls, social-media messages, deleted communications, or location data?

Who knew he had just arrived home?

Were residential cameras, doorbell cameras, traffic cameras, license-plate readers, or nearby commercial surveillance systems identified and preserved?

What is known about the friend reportedly at the door around 2:01 a.m.?

And precisely where was Deqwan when he was shot?

These are investigative questions, not assertions about what law enforcement did or did not examine.

Public reporting provides few answers.

What it does establish is that Deqwan was only 19 years old when he was killed.

Nearly two years later, publicly available information about his homicide remains remarkably sparse.

For his family, however, October 30, 2024 did not disappear from the calendar when the news cycle moved on.

Someone knows what happened that night.

Richard MacDougall

St. Augustine — December 1, 1990

Richard MacDougall was 23 years old and worked construction for Meadors Construction.

During the early morning hours of December 1, 1990, MacDougall and a friend had been at the Shrimp Haven Bar at 169 King Street.

They decided to walk downtown toward the Tradewinds Bar at 124 Charlotte Street.

They never made it.

According to information released by the St. Augustine Police Department years later, as the pair approached Cathedral Place, a verbal confrontation developed between MacDougall and an unidentified man.

The confrontation escalated.

MacDougall was shot and killed on the sidewalk outside 60 Cathedral Place, then the location of Barnett Bank.

The homicide went unsolved.

More than two decades later, St. Augustine police were still asking for help.

In December 2012, around the 22nd anniversary of the killing, the St. Augustine Police Department again appealed to the public for information. Crime Stoppers offered a reward of up to $5,000.

Today, more than 35 years after Richard MacDougall was killed in the heart of downtown St. Augustine, publicly available information about the investigation remains extraordinarily limited.

That raises questions worth revisiting.

Who witnessed the original confrontation?

How many statements were taken?

Did witnesses provide a description of the shooter?

Was a firearm, projectile, cartridge case, or other potentially probative physical evidence recovered?

If ballistic evidence survives, has it been reexamined using technologies or databases unavailable to investigators in 1990?

Were witnesses subsequently re-interviewed, perhaps decades removed from the relationships and circumstances that may have existed at the time?

What physical evidence remains today?

And what does the original investigative file actually contain?

Again, these are questions, not suggestions that investigators failed to pursue them.

But a homicide arising from a confrontation in downtown St. Augustine presents a different investigative landscape from a murder committed without known witnesses in an isolated location.

At least one friend was with Richard.

There was an unidentified man involved in the confrontation.

And there may have been others nearby who saw or heard something.

Someone may still remember.

Two Murders. Two Very Different Investigations.

The Chester case is recent enough that witnesses are likely alive, digital evidence may have existed, and relationships surrounding the victim remain relatively recent.

The MacDougall case presents a different investigative problem: an apparently witnessed confrontation in a compact downtown area, followed by more than three decades during which loyalties, fears, relationships, and circumstances may have changed.

And that matters.

Someone unwilling to speak in 1990 may feel differently in 2026.

Someone who considered a detail insignificant at the time may now understand its importance.

A witness who was frightened then may no longer have the same reason to be frightened.

Technology changes.

Relationships change.

People change.

Sometimes cases can change with them.

We should not pretend that reviewing publicly available information constitutes reinvestigating a homicide.

It doesn't.

The real evidence is in the investigative files.

But public attention can accomplish something important:

It can put a name back in front of the one person who has spent years hoping nobody would ask about it again.

Florida Unsolved Wants to Hear From You

Florida Unsolved is beginning a preliminary review of these cases and would like to hear from family members, witnesses, former investigators, journalists, or anyone possessing documents, photographs, contemporaneous newspaper coverage, or other information concerning:

Deqwan Markell Chester — Apopka, 2024

Richard MacDougall — St. Augustine, 1990

We are particularly interested in locating original source material rather than repeating stories that have accumulated around these cases over time.

For the Chester case, information concerning Deqwan's movements, communications, relationships, or the circumstances surrounding the approximately 1:50–2:01 a.m. period may be particularly important.

For the MacDougall case, Florida Unsolved is interested in hearing from anyone who was present in downtown St. Augustine that night, knew Richard or the people with him, remembers the confrontation, or has knowledge of the original investigation.

Information provided to Florida Unsolved does not replace a report to law enforcement. Anyone possessing information that could materially assist an active homicide investigation should provide it directly to the investigating agency.

And if you were there — or know someone who was — something that seemed insignificant years ago may look very different today.

Cases grow cold. Evidence doesn't necessarily stop speaking.

Florida Unsolved

Cold cases. Missing persons. Unanswered questions.

Have Information About Either Case?

Deqwan Markell Chester: Anyone with information concerning Deqwan's murder should contact the Orange County Sheriff's Office at 407-254-7000 or, to provide information anonymously, Central Florida Crimeline at 800-423-TIPS (8477). Crimeline accepts anonymous tips 24 hours a day.

Richard MacDougall: Anyone with information concerning Richard's murder should contact the St. Augustine Police Department at 904-824-8304. Anonymous information can also be submitted to Crime Stoppers of Northeast Florida at 888-277-TIPS (8477).

If you have information that may be relevant to either case, please contact law enforcement first. You may also contact Florida Unsolved if you are willing to share your information, documents, photographs, or recollections with us as we continue examining these cases.