Cracker Barrel Murders 23 years later: Killer still awaits execution
In the early hours of the morning on Nov. 15, 1995, over 23 years ago, three Cracker Barrel employees worked to prepare the restaurant located off of Collier Boulevard in Naples to open, but it never did.
Donna Howell arrived at the Cracker Barrel restaurant around 5 a.m. to start her shift. She pressed the restaurant’s buzzer to be let inside, and usually her manager would let her in. But after 15 minutes of continuous ringing and pounding, Howell knew something was off and called the police.
Eighteen-year-old Jason Wiggins, 38-year-old Dorothy Siddle, and 27-year-old Vicki Smith were found later that morning by authorities locked in the facility’s walk-in freezer with their hands bound and their throats slit.
Chris Roberts, a sergeant in the violent crimes bureau at the time, was the supervisor of Detectives Jay Crenshaw and Andy Rose who worked the case.
“In ’95 Collier was a lot different really than it is today,” Roberts said. It was a lot smaller of an area for one, and we were just coming off the heyday of being the cocaine and marijuana importation capital of the country.”
Roberts said that Naples at the time was just coming down from some of the stuff in the ’70s and ’80s where we had the cocaine cowboys and square grouper.
“We were just starting the transition into what Collier County has become today,” Roberts said. “Which is a very safe, retirement/vacation destination, and so for that type of crime to happen here, not tied to drugs or anything of that nature, was somewhat unusual.”
Brandy Bain Jennings and Charles Jason Graves, both former employees, entered the Cracker Barrel prior to Howell’s arrival at 5 a.m. killing Wiggins, Siddle and Smith and robbing the store of about $6,000.
Roberts said that when initially talking to the people that worked at the restaurant Jennings and Graves immediately came up as suspects.
“It was one of those things like peeling an onion,” Roberts said in an interview with Naples Daily News in 2015. “Every layer we peeled back made us feel more certain Jennings and Graves were the folks we should be focused on.”
Jennings and Graves were arrested in Las Vegas less than a month after the initial crime and convicted in separate trials in Pinellas County in the fall of 1996.
Jennings was convicted of three counts of first- degree murder and one count of robbery with a deadly weapon and sentenced to three death sentences for the killings and 15 years in prison for the robbery charge.
While Graves was sentenced to three life sentences for the killings and 15 years for the robbery charge.
Jennings made and lost his first appeal to have his conviction overturned in the fall of 1998, and lost all other appeals leading up to his filing of a motion for post conviction relief in 2010.
In 2010, Jennings appeared before a Collier County circuit judge for a Huff Hearing, which the Supreme Court of Florida ruled must be held in all death-penalty cases due to the severity of the punishment. The hearing is held to ensure a defendant’s due process rights are protected. Jennings lost that appeal too.
Most recently, in Jan. 2018, Jennings had his appeal denied by the Florida Supreme Court.
The process of appeals on a death row case can take years.
As for Graves, in the fall of 2002, The U.S. Supreme Court rejected a Naples attorney’s request to hear a challenge to his 1996 conviction.
“Graves’ only chance now is that Jennings will absolve Graves of the murders before the sovereign state of Florida fries Jennings,” said Steve Grogoza, who has represented Graves since the trial in a 2002 interview with Naples Daily News.
But, Jennings has denied any involvement in the murders of Dorothy Siddle, Vicki Smith and Jason Wiggins.
In a four-hour interview after being arrested in ’95 Jennings admitted to robbing the restaurant but blamed Graves for the killings.
Clifford Siddle is frustrated that no execution date has been set for Jennings.
“He admitted he did it, but 20 years later, you’re still feeding him. That’s wrong,” Siddle said in an interview with Naples Daily News. “There’s just not going to be any peace or rest ’til he’s gone.”
Malcom Smith, Vicki Smith’s father hopes to live to see Jennings die.
“I couldn’t be there for Vicki during her last minutes of life, so I want to be there to see his last minutes,” said Malcom Smith, Vicki’s father, in an interview with Naples Daily News in 1998. “I don’t know at this point what I will be thinking or feeling as I watch him die, but I’m just hoping I’ll stay alive long enough to see it.”
