OCALA, Fla. -- Here in the heart of horse country, a world away from the bustle and building drama of Saturday's Belmont Stakes on Long Island, a majestic chestnut thoroughbred named Yankee Boss peered over the front of his stall, as if taking in the vast pastoral expanse of Kinsman Farm.
Only a few feet away, Jessica Steinbrenner looked at the promising 2-year-old and smiled. The colt she named in memory of her famous father looks to have a bright future in the family business. The operation has produced big-name contenders such as Grade 1 winner Bellamy Road, although no candidates appeared in this year's Triple Crown field. But Yankee Boss may one day engage in the same relentless pursuit of winning and excellence that defined the real Boss, the late George M. Steinbrenner.
Jessica, who has become a respected executive in the thoroughbred industry, moved closer and nuzzled the equine namesake. You can see the special connection emanating from her light blue eyes, bringing to mind the familiar eyes of her dad. His legendary gaze could pierce managers and multimillion-dollar ballplayers, or just as easily warm the hearts of people in need, the beneficiaries of his many charitable endeavors.
"I know my dad is watching down and feeling proud of us," she said, steering a cart across a hilly stretch of land to her office, joined by a reporter and one of her four children, college student Robert Molloy.
Jessica, 47, runs the Kinsman thoroughbred operation that was once a passion of her father's. She presides over the sprawling 880-acreage that served as a home away from home for the Boss; his wife, Joanne; and the rest of the Steinbrenner clan. Jessica's brothers, Hal and Hank, handle the day-to-day operations of the Yankees, with sister Jennifer also contributing on the baseball front. All four share in the baseball responsibilities as general partners, and feel a deep commitment to maintaining the winning tradition of the Yankees, as established by their father.
"The game is never going to see another person like him," Jessica said. "All four of us combined don't have his vim and vigor. But we're all pretty good at what we do. So give us time."
It's been only 11 months since George Steinbrenner died of a heart attack at age 80, following a decline in health that prompted him to pull back from daily control of his enterprises, delegating those duties to his children. But the pain of his passing is still fresh for Jessica. Sitting at a conference room table, along with Kinsman Farm manager Jim Scott and vice president Kevin Adler, she talked about how much Steinbrenner loved to make special visits to the farm to look in on the yearlings.
"Toward the end, when he couldn't make it up here, Jim videotaped each of the yearlings crossing over, coming to the training barn for the first time, and would announce who they were, so my dad could see his farm," she said. Her voice trailed off, and tears streamed down her cheeks.
"Up to the end, he still wanted to know about the horses. He'd ask me, 'Do you think he's the one?' And I'd go, 'He could be the one, Dad.' He was aware of Yankee Boss. But he never would have wanted a horse named after him early on. Never. Still, I think he was glad that I did it for him."
Jessica talked about what she calls her "all-star" team: Scott, who knows everything about caring for the farm's horses; Adler, an expert in breeding and racing; trainer Juan Rodriguez; and her husband, Yankees executive vice president Felix Lopez.
"As a group, we work beautifully together," she said. "Jim knows the medical side of it. Kevin is magnificent with records, and we look to Juan to train a good horse. My husband has a construction background, and that's a big help with all the buildings we have on the property. It's a great team, and every one of us plays an important role."
Jessica described herself as somewhat introverted, similar to younger brother Hal. She said she was always considered the easygoing child, the third of four Steinbrenner children. But as the head of Kinsman Farm, she's a chip off the old Boss, becoming more and more like her hard-driving father.
"I have to be in control," she said. "I have to be touching things, seeing things. And they'll get a little annoyed with me sometimes, but I want to know everything that's going on. It would be difficult for any one of us -- me, Jim, Kevin or Juan -- to do a job that didn't make us happy. Because there are phone calls at 3 a.m. There are horses born every day of the week. There are emergencies at the track every day of the week. And there's no time in this business we can be without our phones. I'd never just step away for a day -- and neither would they."
Perhaps not surprisingly, Jessica has developed a touch of her dad's well-known temper. "I'm getting it," she said with a laugh. "Now that I have a little bit more responsibility, with that, I might lose my temper, because I so badly want this to work. I want everything to be the way it needs to be."
Farm manager Scott offered a perspective on that, having worked with the Boss for many years. "It's a little different between her and her dad," he said. "She's way more approachable. If George was having a fit, you just kind of shut your mouth and hid a little bit. I feel like if she's angry about something, I can still come back and make my case. She's like a sister to me. We have spats and fuss at each other. But I respect her, and she does a great job."
"She pushes us to be better," Adler added. "She doesn't think so, but she does. Because we want to make sure we have everything done for her the best it can be done, whether it's research or anything involved with the horses. And her father was the same way. We always did above and beyond to make sure everything was taken care of."
Jessica's love of horses began in childhood. Born in Ohio, she moved with her family to Tampa when she was a fifth-grader, but the farm was almost always part of her life. Her father purchased it in 1969, four years before he bought the Yankees and began rebuilding them into World Series winners with his renowned blustery, hands-on style.
Jessica recalled how, at age 5, she would sneak out of her parents' Kinsman house in the early mornings and walk to the barns to visit the horses. She taught herself to ride on a Shetland pony. And eventually, her dad let her ride his 1973 Illinois Derby winner, Big Whippendeal.
Her grandparents, Henry George and Rita Steinbrenner, frequently stayed at the farm, watching from their lawn chairs as Jessica practiced jumping. She remembers one experience vividly: "They'd watch me jump over and over, and my grandfather would say, 'Do it again,' and I'd go, 'Again?' and then I'd jump the same two fences 20 times. One time I fell off and caught the horse. I went over to take him to my grandparents. My grandfather said, 'What are you waiting for?' I said, 'I just fell off.' And he said, 'Well get back on.'"
That lesson embodied a way of life for all the Steinbrenners, and guided Jessica through school at Culver Girls Academy in Indiana, and later at Sweet Briar College in Virginia, where she continued riding and kept her passion for horses. After college, she worked as a TV news production intern, and for her dad. In 1986, she married Joe Molloy and focused on starting a family. The couple had four children, two boys and two girls. She fondly remembers her young children and their cousins cavorting with their grandfather in his office at the farm.
"My dad was a tough boss. I mean he was tough," she said. "And when it was real tough, and the checks had to be signed, they called me to get my sister to bring her daughter Haley in, so he'd be signing checks and crawling around after her on the floor. It was hysterical to watch."
She chuckled at another recollection.
"Sometimes he'd come to our homes and not give you a heads-up. And I had four children under the age of 5. But he'd show up at my house, and I'd yell to the kids that 'Bumpa' was here -- and immediately they were picking up all their toys. I lived in a three-story house, and by God if he wouldn't go all the way to the third floor to check on the kids and to see if the beds were made and that everything was put in its place."
She paused to pull out her cellphone, then displayed a family shot of the Boss on all fours with her four kids riding on his back, as if he were a big, gentle horse.
"This is my dad," she said, looking at the old snapshot. "It captures exactly how he was with the kids."
Joe Molloy played a key role in the Yankees' front office as managing general partner, but left the franchise in 1997 after he and Jessica divorced. She focused on her kids and became more involved in the operations of the farm. She also dabbled in writing. She authored two children's books: "My Sleep Room" (2004) and "My Messy Room" (2006). For the past six years, she's been married to Lopez, who worked on the construction of then-Legends Field, renamed George M. Steinbrenner Field in 2008, the Yankees' spring training home in Tampa.
Her father had begun to pull back from the running of his sports empire due to health issues. Looking back, Jessica said she cherishes the extra time they had together as a result.
"I was so very thankful over the last few years that we were able to spend so much time together," she said. "Because [when I was] a child growing up, he was busy working. And the last few years of [his] stepping back a little let all of us kids form relationships with him in a father-daughter, father-son way. He was always a good dad.
"But he had to travel a lot for baseball and his various activities. So that time together was a gift."
Dividing her time each week between a home in Tampa and the farm, Jessica handles the work, knowing that her father's legacy is flourishing.
"All four of us want to carry it on," she said. "It's absolutely a comfort -- whether it be Yankee Stadium, the stadium in Tampa or here, knowing that my Dad was in all these places, and that we are all trying to do what one person did before. We're all working our tail ends off trying to do that. We may or may not be successful in the same way. But I don't doubt for a moment that all four of us will be successful. We'll work until we are. But it's some big shoes to fill."
Jessica is doing her best. She doesn't dream of winning the Kentucky Derby as her dad did. She'd prefer a Breeder's Cup champion, and to simply run a successful, profitable thoroughbred business, a business with many emotional ups and downs and unexpected injuries to horses, as happened this year.
"Every time you send one of your horses off to a track to train, it's like sending them off to college," she said. "You hope for the best, but you never know what will happen."
She and her colleagues have high hopes for a number of their horses. They're excited about the prospect that an offspring of Bellamy Road -- an in-demand sire these days -- might emerge as a contender. Another popular sire and successful racehorse for the Steinbrenners, Majestic Warrior, has produced a promising colt named Yogi Berra, with Yogi's full blessing.
And of course, there's a special one that will soon be heading off to New York to train at Belmont -- Yankee Boss.
Forgive the Boss' daughter if that colt inspires a deeper connection.