The Money-Fueled Murder of Kentucky Dairy Queen Owner Anna Mae Branson

Anna Mae Branson was an 85-year-old Kentucky businesswoman and philanthropist who was found stabbed to death in her Kentucky home in January 2003. 

She had been well known in her hometown of Madisonville, Ky., as the successful and generous owner of one of the state’s first Dairy Queen fast food restaurants. She grew the operation, which started out as a small franchise in Madisonville, into a successful business worth millions of dollars. To her many employees, it seemed that ”Ms. Anne” was always impeccably dressed—hair and makeup done to perfection. While she was a widow with no children of her own, Branson reportedly had great affection for her family, including siblings and many nieces and nephews who have fond memories of the large family gatherings she used to host at her home. At the time of her murder, she was engaged to a retired eye surgeon.

On the evening of January 12, 2003, Branson attended church for the last time. The next day, she was found deceased, sprawled at the foot of her basement stairs. She had been hit on the head seven times with a blunt object and stabbed 97 times. Defensive wounds on her forearms and bloody fingerprints on basement furniture indicated that Branson had tried to defend herself from the furious attack.

Strangley, there was no apparent evidence of a break-in; all of the household valuables appeared to be untouched, and Branson’s diamond ring was still on her finger. Investigators suspected her killer would likely have been someone Branson knew and trusted enough to let into the house, all the way down into the basement.

After investigators brought each of her siblings in to be questioned by a polygraph test, they began to suspect that the son of Branson’s brother Earl, a man named Russell Winstead, had somehow been involved. 

Winstead was a coal miner by trade as well as a husband and father to five children. Initially, Winstead’s wife, Terri, corroborated his alibi for the night of the murder. She told police that her husband had been at home with her at the time of his aunt’s death.

However, the seemingly mild-mannered family man had a secret. He had for years been struggling with a severe gambling problem and amassing mountains of unpaid loans that he had kept hidden from his wife and family.

After receiving a tip from a co-worker of Winstead’s about his gambling issues, the police discovered that he had been leading a double life, carrying on a romantic tryst with a girlfriend at a local casino in addition to wracking up tens of thousands of dollars in unpaid gambling debts. After investigators discovered a financial ledger book in Branson's house that showed Winstead owed his aunt more than $60,000, they began to suspect that Winstead had killed his wealthy aunt after she declined to extend a loan to cover his debt. 

During the investigation, police revealed to Winstead’s wife that casino records showed he had spent more than $1.5 million dollars gambling, sometimes losing between $10,000 to $40,000 in a single night. She later withdrew the alibi she had provided, eventually testifying in court that her husband had asked her to lie for him and coached her on exactly what to say to investigators.

Hidden underneath Winstead’s mattress at home, police found a knife that would’ve made wounds consistent with the ones suffered by Branson.

Before he could be arrested for the murder, Winstead fled the country. 

Living in Costa Rica on the run for just under two years, Winstead was eventually arrested in San Jose after a tip from the TV series America's Most Wanted led to his capture.  A deal was reached to extradite him back to the United States in return for not facing the death penalty, which is illegal in Costa Rica. He was charged with murder and first-degree robbery and pleaded not guilty. The trial featured a courtroom divided, with half of the family sitting on the prosecution's side and the other half sitting with the defense.

During the contentious trial, after seeing Winstead’s picture in a newspaper, a witness testified for the prosecution that she had seen him leaving Branson's home on the night of his aunt’s murder. 

Then, another man, Fred Roulette, a former jail cellmate of Winstead’s, wrote a letter to the judge saying that it was him who had killed Branson. He provided details of the killing, including specifics about the murder weapon and scene of the crime that had not been released to the public, and he also said he had driven to Branson's house and killed her after she refused to rent him a house. However, Roulette, too, would eventually recant his testimony, explaining that he had only written the letter because Winstead had promised to set up trust funds for Roulette’s children. 

Some members of the family remain skeptical that Winstead would have been capable of such a horrific killing. He admits to owing his aunt money, but no scientific evidence linking him to the crime was ever discovered. 

In 2007, Winstead was convicted of the murder and robbery of his aunt and sentenced to life in prison. He will be eligible for parole in 2030.