Next Saturday, Nov. 15, will mark 30 years since one of Collier County’s most heinous murders in modern history. The following is from a Nov. 14, 2015, article in the Naples Daily News entitled “Cracker Barrel murders 20 years ago haunt families” by Jessica Lipscomb.
On a Wednesday morning 20 years ago, three employees worked before dawn to open up the Cracker Barrel restaurant off Collier Boulevard.
Eighteen-year-old Jason Wiggins had stayed overnight to clean up. Manager Dorothy Siddle, 38, arrived around 4:30 a.m., and 27-year-old cook Vicki Smith showed up about 10 minutes later. But before the restaurant could open that morning, all three were dead.
The killings at Cracker Barrel were unlike anything that ever had happened in the community, said Chief Chris Roberts of the Collier County Sheriff’s Office, who was then a sergeant in the violent crimes bureau.
“At that time, it was one of the most heinous crimes in Collier County,” Roberts said. “You just didn’t see that sort of thing in Naples, Florida, back then, no more than you see it today. We were just coming down from some of the stuff in the ’70s and ’80s where we had the cocaine cowboys and square grouper. We had murders related to those, but something like what happened at Cracker Barrel wasn’t common at all.”
After two failed attempts to rob the restaurant, Brandy Bain Jennings and Charles Jason Graves — both former employees — entered the Cracker Barrel on Nov. 15, 1995, stealing about $6,000 and killing Wiggins, Siddle and Smith, who were found in the freezer with their hands bound and their throats slit. Jennings and Graves were picked up by police in Las Vegas after Collier County investigators issued a nationwide bulletin.
The investigation had quickly pointed to Jennings and Graves as detectives spoke with other employees in the days after the robbery.
“It was one of those things like peeling an onion,” Roberts said. “Every layer we peeled back made us feel more certain Jennings and Graves were the folks we should be focused on.”
Detective Andy Rose was driving to North Florida with his partner, Detective Jay Crenshaw, to meet with Graves’ family when they got word that the suspects had been arrested in Las Vegas. Somewhere around Tampa, the two detectives turned around and hopped a flight from the Southwest Florida International Airport with just one change of clothes.
At first, Jennings didn’t want to talk to the detectives, but the next morning, he changed his mind, giving a four-hour interview where he admitted to robbing the restaurant but blamed Graves for the killings.
“His entire story took us from before when it happened basically to the point where we were that day,” said Rose, now a police commander in North Port. “He was very cordial and seemed to be pretty forthcoming with everything.”
Graves and Jennings were convicted in separate trials in Pinellas County in the fall of 1996. Graves was sentenced to life in prison, while Jennings received the death penalty.
May 18, 2025
Jennings died of cancer after 29 years on death row, the Florida Department of Corrections confirmed.
This article originally appeared on Naples Daily News: From the Archives: Three decades since infamous Cracker Barrel murders in Naples
Reporting by Naples Daily News / Naples Daily News
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