Mother Knows Best

Carolyn Kessinger's journey from childhood to motherhood to ushering in the next generation.


Carolyn Kessinger wears a lot of hats—real estate broker, attorney, baseball fan and pickleball player, to name a few. But it is her longtime role as a wife, mother and grandmother that she considers the most meaningful of her life.

A self-proclaimed small-town girl who grew up in Forrest City, Arkansas, Carolyn married her husband, former Ole Miss Rebels and Chicago Cubs shortstop Don Kessinger, when she was just 18 years old. “I’ve always been a sports girl,” she says, admitting she never thought she’d marry an athlete. The couple moved to Chicago immediately after, and Carolyn figured out quickly she’d need to study up. “I thought I knew about baseball, but truthfully I knew about three strikes and four balls,” she says. “These women started talking about ERAs and power percentages, and I thought, ‘What?’”

Two years later, just as she had begun to grow used to the nuances of the game, she and Don—“Donnie,” as she calls him—welcomed their first son, Keith. Carolyn, who says she was at a disadvantage from having no babysitting experience growing up, felt just as lost about motherhood as she had about ERAs and power percentages. For the first three weeks of Keith’s life, Carolyn stayed with her parents, leaning on her mother to learn the ropes with Don’s spring training fast approaching. “You can’t go to spring training by yourself with this baby,” her mother told her. “I’m a married woman, and I’m going to spring training to be with my husband,” Carolyn replied.

Shortly after, Carolyn boarded a plane to Arizona with a newborn in tow. “We had a little efficiency apartment and the only way I could warm bottles was on a plate warmer,” she says. “And you know what? I came back a professional.” Even when she got the hang of it, Carolyn still heeded her mother’s advice. “My mama said it’d come naturally and it’s true,” she says. “I didn’t know what I was doing, but whatever I did became normal between [us], and that’s just part of motherhood.”

“I’m sure not any other mother in the world would’ve done it like I did it, but it worked for Keith and me.”

Keith grew up attending his father’s games, soon developing his own love for baseball. The Kessingers lived in an apartment complex in Chicago near other baseball families, so he always had play dates.

When Keith was two years old, the family bought a house in Chicago and were soon expecting their second child.

“Here I am with this little belly, and I didn’t know what it was going to be. But Keith was going to have a brother to play ball with him,” Carolyn says. “He wasn’t even three, and he said, ‘I’m gonna have a brother to play ball with me.’”

Keith was right, soon welcoming his little brother, Kevin, but not in the condition he expected. “Can I tell you the look on Keith’s face when we brought this baby out—the first thing he said was, ‘He can’t play ball with me!’”

Carolyn says she was always stunned when people would ask her how she convinced her children to like baseball. “They grew up with it. Keith and Kevin’s first word was ‘ball’–not ‘mama,’ not ‘dada’ or ‘bye-bye.’ It was ‘ball.’” Her children grew up surrounded by baseball, going to almost all of their dad’s home games in Chicago and away games from time to time. “I had one stuck in my coat and the other one with a scarf wrapped around him bundled up because baseball is a wonderful life,” she says.

Baseball can also be a lonely life. Don was on the road for half of the season, meaning her efforts were primarily focused on giving the boys as much of a normal life as possible. “It would have been a terrible life if I hadn’t been married to the love of my life,” she says. “But we had a storied journey.”

Once the boys started playing sports, life got a little tougher. “The boys wanted to do their thing, and they should get to do their thing, so I was taking this one to practice, taking that one to practice, throwing balls to this one, catching balls from this one—until they got too big and then I couldn’t do that anymore.”

Living in the Midwest was not without a fair share of cultural disconnect for a Southern family like the Kessingers. When Keith started school, he brought work home showing several mistakes despite knowing the material, which he attributed to his teacher’s pinched nasal accent.

“He didn’t understand the way she was saying her words because she was a Yankee and he was a Southerner,” Carolyn says, laughing.

She also watched her sons deal with the pressure of growing up with the Kessinger name in Chicago. “There’s a lot of failure in baseball, even for the best,” Carolyn says. “The best hitters in the whole game hit 300. That means they fail seven out of 10 times. There’s nothing in our world we could fail seven out of 10 times and be the best, and they are.

“Donnie wasn’t going to do it every time, I assure you (Keith and Kevin) weren’t going to do it every time. That was hard for me as a mom.”

Carolyn fought to protect her children from the ugly side of baseball and brutal fans when Don didn’t play his best game.

“I didn’t realize the pressure,” she says. “He’d get in the car to drive home with two sweet, dirty little boys who would be chatting and we would talk baseball all the way home. … He was just so positive.”

Even on days when Don might have played two games, he remained a father first when he got home, hitting high pop-ups with a tennis racket just because his sons wanted him to or having the neighborhood children over for a ball game in the front yard, resodding it every summer without complaint.

After Don’s retirement from baseball, the family returned to the South, settling in Memphis.

In high school, at Briarcrest, the two brothers got to play on the same team – Keith as a senior shortstop and Kevin as a freshman outfielder, which meant the family no longer had to split their time between different games in different places. Naturally, the family was delighted when Keith signed at Ole Miss to continue his baseball career, and Kevin followed.

Carolyn had mostly mastered the routine of being a baseball wife and a baseball mom, but maintained her goals, earning degrees in math and science from the University of Memphis (then known as Memphis State) and teaching geometry and algebra. Law school soon followed, with Carolyn still determined to watch her boys play, even if it meant having a book in her lap so she could study during the game.

Life in Memphis was rapidly shifting south, literally, with Don taking the head coaching job at Ole Miss and Keith and Kevin in Oxford, both playing for their dad.

Carolyn commuted to Memphis each day for work after they moved to Mississippi, a grind that eventually became too much to handle.

“I just decided I’d come down here and hang my own shingle and I did,” she says, practicing in Oxford from 1992 to 1997.

During that time, Carolyn’s father passed away and her mother, only a few decades removed from serving as Carolyn’s support system when she became a mother, moved in with them. Her mom had always helped her with everything, from running for class president to helping her set up her apartment when she left home to traveling to baseball games. It was natural for Carolyn to return the favor, especially with their shared love of the game.

“She was such a sports lady,” Carolyn says. “Girls back in my day didn’t play. It was unladylike to play sports. I felt so cheated. My brothers got to play and I didn’t, and I was better than they were.”

Carolyn’s father was a doctor who used little black books for note-taking. Her mother had her own use for them, using the pages to record every box score from every pro game Don ever played. “She kept every single thing,” Carolyn says.

Even in the last years of her life, Carolyn’s mother never hesitated to travel and watch the family play. Sometimes Carolyn had to put a hand on her leg to calm her nerves or tell her not to be so hard on an umpire.

When her mother fell ill, Carolyn wound down her law practice to become her caregiver. She died in the Kessingers’ home, Carolyn holding her hand. “My parents were very Godly parents and raised four good children,” she says. “Their legacy goes on through my children and my grandchildren.”

For all its joy, motherhood comes with plenty of disappointment along the way. For Carolyn, her sons’ letdowns were also hers, as was the case when Keith—drafted out of college by the Baltimore Orioles before landing a spot with the Cincinnati Reds—decided it was time to walk away from his dream of playing major league baseball.

“It was such a hard decision for him, and we knew it was,” Carolyn says. “…for him to have this realization that he wasn’t going to get there and have him make that decision was very hard for me as a mom.”

Disappointment struck once again when her younger son, Kevin, suffered a back injury his senior year at Ole Miss. Playing for his father with the team trying to get to the regional playoffs, Kevin played through the pain, which tortured Carolyn. “I was ready to go to the field, to the dugout, to get his dad by his collar and say, ‘Do not play my child again,’” she says. Kevin signed professionally with the Cubs but was never able to play due to his injury. “At some point, whether or not you get to the pinnacle of success in your chosen profession, it’s over,” Carolyn says. “My saddest moments were what I consider to be their greatest disappointments. Just from a mom standpoint, you want them to get to do their dreams.”

Now that her children are grown with children of their own, Carolyn has come to experience the joys of being a grandmother to a new clan of Kessingers: Josh, 22; Anna Kathryn, a junior at Ole Miss; Grae, a freshman shortstop for the Rebels; and Chase, a senior at Oxford High School.

Staying true to form, Carolyn remains involved with all of her grandchildren’s activities, from hunting to shopping—and of course, baseball.

“Grandparenting is wonderful,” she says. “I loved being able to watch them grow up because we really got to enjoy, daily, everything they’ve done.”

“I loved being a mama, but I have really loved being a grandmother.”

Peggy Sneed, a longtime friend of the Kessingers, knows how dedicated Carolyn is to her family. “She’s just the best mother and most supportive grandmother. It’s nothing for her to go to two different games in two different cities in one day,” Sneed says. “She has totally devoted herself to her boys and her grandchildren and just wants the best for them.”

Don, now marking 52 years of marriage to Carolyn, embraces how lucky he’s been, how lucky they all are to have her at the helm of the family’s cheering section—on and off the field.

“I’m so blessed to have her along this journey with me,” he says. “She’s been the most wonderful wife, mother and grandmother in the world.”

Carolyn and Don attend as many of Grae and Chase’s baseball games as possible, traveling to away games when they can. Even as a grandmother, Carolyn feels the pressure the youngest generation of baseball-playing Kessingers must feel. “They seem so young to me,” she says.

“There’s still expectation with that name on their back.”