They made their fortune in, of all things, a Dairy Queen. It was one of the first chain restaurants in the little town and year after year, generation after generation, it was the teenage hang-out.
Ann was an icon in Madisonville. “Prominent businesswoman” was how the newspapers described her.
Ann and Carroll had no children. But eight years after their marriage, Carroll’s brother married Ann’s sister. This couple’s only child, a towheaded blue-eyed boy, became the focus of Ann’s maternal instincts. He was like her own son and she was like a second mother to him. That boy was Jack, my husband.
Jack and I grew up in Madisonville, too. We were high school sweethearts and as soon as we were old enough, we married. I knew of Ann before I knew Jack. Everyone knew Ann, Carroll and the Dairy Queen. For all of us growing up in the small western Kentucky town, the greatest amusement on Saturday night was “circling the Queen” to wave at friends and maybe pull in and give a carhop your order for a cone.
Growing up in the midst of small-town Americana, Jack and I had goals and borders that reflected our surroundings. When a high school newspaper reporter asked senior Jack his long-range plans, he reached for the hand of his steady girl and replied, “To own the Dairy Queen and raise little Dillies.” It was my hand he was holding.
But Jack and I soon dreamed dreams that couldn’t come true in Madisonville. His career as a federal agent caused us to move several times, each time to a larger city. And eventually, Ann and Carroll retired, selling the Dairy Queen and erasing the Branson-DQ icon for future generations.
Carroll spent most of his retirement creating intense and moving works of art that you’d never imagine coming from the hands of the once farm boy. Ann had more difficulty weaning herself away from business. She occupied herself buying, fixing up and renting a good chunk of Madisonville’s real estate. She busied herself further with church work, bridge clubs and an occasional cruise.
In 1994, Carroll died of cancer and Ann became a rich widow. She was still the envy of most women in the town. She possessed that combination of qualities most of us long for. She was rich, successful, smart and beautiful.
Ann had a closet full of furs and no less than twelve carats of diamonds in the rings she wore with her everyday wardrobe. She lived alone in a stately 1923 Dutch Colonial home, where every piece of antique furniture and every accessory was unique and carefully chosen.
She eventually tired of the old home and the antiques and was planning to build a new home in an exclusive area, on a lot overlooking a lake. She’d purchased the lot but builders had not yet broken ground.
Ann, however, had not given up on life or the future. She now was engaged to an eye surgeon, but she wasn’t sure she was ready to settle down, at least not yet. He was working diligently to persuade her to marry him, but she had decided to wait until her younger sister, Grace, died. Grace had been diagnosed with small cell lung cancer—oat-cell carcinoma—more than two years earlier. It had spread quickly, and she had long ago outlived her doctor’s expectations. Ann figured she had less than a year left. She alternated Grace’s care with other relatives, but as the oldest of five siblings, she felt the strongest responsibility for her unmarried sister.
Ann would have been beautiful without the furs and jewels. Heads turned when she entered a room, admiring her slim body, chiseled face and graceful demeanor. She dressed tastefully but flamboyantly. She had a certain presence that no money could buy, though if there’d been a price tag attached, she could have paid it.
Ann was a bridesmaid at our daughter’s wedding. Penny decided she wanted only family members in the wedding party—people who still would be dear to her years later—and I was privileged to be both matron of honor and mother of the bride. Penny’s three “grandmothers” were her attendants—my mom, Jack’s mom and Ann.
She loved being in the wedding, from the pedicures that resulted in periwinkle-hued toenails to the bridesmaids luncheon at the quaint German restaurant. In the photo of her walking down the aisle, Ann’s face is animated, her eyes are sparkling and the smile inching across her face looks just seconds away from a joyful laugh. All eyes were on her that day (something she was comfortably acquainted with) and she loved it.
Ten months after the wedding, Ann was murdered.
A few weeks before the murder, Ann spent Christmas with us, as she had done each year since Carroll’s death. She and her sister Iva Ray—Jack’s mother—drove from Kentucky to Georgia in Ann’s crimson pearl Cadillac Seville. We stayed up late playing Rook, laughing and good-naturedly accusing each other of cheating.
“You Winstead sisters can’t be trusted,” joked Jack to Ann, referring as he often did to the sisters’ maiden name. “Before you know it, we’ll see your picture plastered all over television.”
Before we knew it, we did.
The last time I saw Ann was the day after Christmas. She was wearing one of the gifts we gave her the day before, a black cape with a leopard skin collar. I often thought, I hope I look that good when I get to be her age. Then I’d remind myself: Too late. I don’t look that good now, and I’m decades younger.
Jack walked to the car with Ann and his mom, carrying their luggage.
“Thanks for the Christmas money,” Jack told Ann.
“I’m sorry it wasn’t more,” Ann replied. “Next year, it will be.”
Jack remembered that being an unusual comment. Ann strapped for money? Not likely.
I stood at the door with our grandson, Taylor, and waved good-bye.
“Good-bye, Winstead sisters,” called ten-year-old Taylor. Ann pulled her head from the car’s trunk, smiled and waved. Her chestnut hair was perfectly styled, her makeup flawless, her smiling face framed in leopard skin.
Saturday, January 11, 2003. I packed for a short trip to Alabama the next day. Jack phoned his mother, then Ann. Ever since Ann was widowed nine years earlier, Jack had made it a habit to call her once a week.
Jack came into the bedroom as I finished packing.
“Did your mom have anything to say?” I asked.
“No, not really,” Jack said matter-of-factly. “Her leukemia’s flared up again. She said it’s not serious, but I can’t help worrying about her.”
I nodded. “What about Anna Mae?” Only close family called Ann by her full name. In fact, Jack and I were about the last hold-outs.
“No big news.” Jack paused, then added, “I told her she needs to kick that crazy renter out.”
“He’s still bothering her?”
“Yeah. He calls her in the middle of the night, begging her to come over and chase the ghosts out of his attic. She said she’s not afraid of him, but he makes her uneasy. I told her to have Earl evict him if she didn’t want to.”
Earl was Ann’s younger brother. All five siblings lived within a few miles of each other—two brothers and three sisters. Earl was a widower with grown children, so he was the self-appointed protector who repaired broken locks, helped the sisters find a good plumber and chased away scary renters.
“Anything