A Man and his Mountain

To Donna, Gaby, and Eben, Sláinte, Budem, L'chaim, Cheers!

Prologue

Catch Me If You Can

He watches Rachel walk past, mere minutes now before her big moment. Their moment. She doesn't spot him in the crowd, but he is transfixed. For what seems the hundredth time in their still-new relationship, he feels the tightening at the back of his throat at the mere sight of her. Even at his age, his wavy hair reduced to gray stubble, he squares his shoulders and stands a little straighter in unconscious response to her lithe grace, her shining, impossible youth. He can scarcely believe Rachel is his, yet there she walks, dressed in the gold that he picked out for her, exquisite in the afternoon sun.

Jess Stonestreet Jackson is not a man who casually reveals his heart. Even those closest to him—especially those closest to him—know this all too well. This beat cop turned billionaire, this gentlemanly cutthroat wine mogul, has made his friends, his employees, his children, and his wives into Wine Country Kremlinologists. Always they must labor to crack his code, to puzzle out the meaning of a glance or frown or too-broad grin. Only Rachel lays him bare. Years after this morning has passed, recalling how she looked, that perfect moment, Jess's voice will crack. His eyes will well. He had arrived with her certain they would make history that day. Amid a chorus of doubters, he had been sure of it.

And if there was one thing Jess Jackson loved even more than Rachel, it was showing a dubious world that he was right.

The Preakness Stakes transforms Baltimore. Once a year this blue-collar port town gives way to the pomp and ritual of one of the oldest sporting events in America, the middle leg of the storied Triple Crown, the Super Bowl of horse racing. Here he would make his stand, an occasion marked by a full week of hot-air balloon races, footraces, pub crawls, parades, live music throughout town, and endless arrangements of bright yellow black-eyed Susans, the state flower and the symbol of the Preakness. Culminating with the legendary stakes race at Pimlico Park, the Preakness has been Baltimore's biggest annual celebration since Ulysses S. Grant called the White House home back in 1873.

In 2008 Jess Jackson brought two things to this party: an impossible horse and a very large bodyguard.

Both horse and guard were results of Jackson's penchant for defying tradition and irritating the rich, powerful, and entrenched. This child of the Depression who worked his way through school as a dishwasher, lumberjack, ambulance driver, fashion model, Teamster, stevedore, and cop had little in common with the gentry of Horse Country, who certainly viewed him as a barbarian. But that hadn't stopped him from using his California Wine Country millions to snap up farms, fillies, and fans. In the same daring, risky, convention-defying way he had built a faltering little winery called Kendall-Jackson into an empire that quite literally put Chardonnay on America's tables, Jackson had, after a few initial disasters, become the most successful new racehorse owner in half a century.

This was not supposed to happen. Corporate scions and other assorted rich guys were always showing up in Horse Country (and Wine Country, for that matter) certain their mad business skills would set them apart. The old guard with the blue grass and blue blood found it highly entertaining because the newcomers invariably skulked away with egos and wallets deflated. And yet here, infuriatingly, was Jess Jackson, transforming a staid and insular thoroughbred industry against its will, as he had previously done in the wine business. He flouted convention. He denounced the corruption others pretended not to see. Worse, he was not just a California winemaking interloper; he was, of all things, a lawyer, too, and he would never be forgiven by the old guard for suing the pants off famous (and, thanks to Jackson, infamous) horsemen for cheating him. Hence the death threats that prompted the bodyguard, along with backroom attempts to block him from entering this marquee race. The obstructionists failed in the end, although Jackson's horse was stuck in the absolute worst starting position possible, a handicap no other horse had ever overcome.

But this time the horse was Rachel Alexandra, a three-year-old filly in the midst of one of the great racing campaigns in the history of the sport. Her previous race just two weeks before, the Kentucky Oaks, had set her apart. That race—a $500,000 contest at Churchill Downs for three-year-old fillies held on the day before the Kentucky Derby—had stunned racing fans as Rachel won by more than twenty lengths, by far the largest margin of victory in the history of that race. Jackson had been a spectator, not an owner, for that one, but after he saw Rachel run, he had to have her. He was one of the four hundred richest men in the world at that point, and no price was really beyond him—a thought that, after so many years, still startled him when he took the time to reflect on it, still etched his broad face not with pride but with something that looked very much like discomfort. He had never lost the poor kid's unease at spending, the idea that thriftiness, not lavishness, was the thing to be admired. This was a guy who still wore his grandfather's hand-me-down boots, after all. "Plenty of wear left in them," he'd grouse when someone asked him about the broken-down old things. So for a long time he wouldn't say how much he had paid for Rachel, pretending it was a secret deal of some sort when in fact he was simply embarrassed. When he finally admitted the price tag had been $10 million, he looked sheepish but confessed no regrets. "She was," he would say in a tremulous tone, as he if he were explaining how he had come to possess the Mona Lisa or achieved the summit at Everest, "worth every penny." And to him, Rachel was his latest Mona Lisa, and the campaign he had designed for her was his latest mountaintop.

Her previous owner had not planned to enter the Preakness. He didn't believe in running females against stallions, which was a prevailing view among the racing elite. But Jackson had immediately announced his intention to enter the race, notwithstanding the tumult brought on by a new stable, a new trainer, a new jockey, and almost no time left to prepare. The other owners predicted disaster. No way could Jackson prep her in time. And even if he did, there was no way a three-year-old filly, no matter how talented and successful against other females, could stand up to a field of stallions in one of the biggest races in the world. Didn't this outsider, this meddler, understand anything about thoroughbreds? He wasn't just going against tradition. He was going against nature. A filly hadn't won this race since before the Great Depression with good reason. It lay in the female horse's genes, her most ancient instinct, the cardinal rule of the herd: to back down when challenged by a male. Rachel Alexandra would be facing a whole field of the horse-racing game's most alpha males. The old guard of the thoroughbred industry had chortled, delighted at the prospect of Jess falling on his face at last despite his billions, despite his empire of wine and real estate and California hubris, and especially despite his incessant talk of innovation and reform for horse racing. They wanted him to look like a fool. They wanted him to go away.

Rachel is in the gate now, done prancing and snorting, her usual prerace temper replaced by a tense stillness. He had never encountered a horse like Rachel, so anxious to run, so competitive, so focused. It had been eighty-five years since the last filly won the Preakness. And no horse, male or female, had ever won the race from the starting place Rachel had been given: the thirteenth post position, the farthest from the rail, the longest road to victory. That spot had never seen a winner. Never in 134 years.

Just another bit of history to make, Jess figures. He rubs his eyes and raises his binoculars, gazing from the owner's box. He can see she is perfectly still now, a coiled spring at the gate, dark and gleaming in the sun. The unbearable pause after all the horses are in line stretches on for way too many heartbeats. Jess tries to take it all in: the expectant crowd, his wife beside him quietly chanting encouragement to Rachel, the warmth of the sun on his shoulders. This is one of the moments he wants to squeeze tight and hold close and keep vivid. Like the time he perched on his favorite uncle's shoulders as they watched Seabiscuit run back in 1938. There was the first time he saw his firstborn. That disastrous, delicious first Chardonnay he made, the one that almost broke him, then made him rich. And that first case of wine he sold, at the Oyster Bar at Grand Central Station of all places. And the next thing he knew, the First Lady was pouring it at the White House. His wine at the White House: that had been huge. He knows he doesn't have many more moments like that left to him, that he has already probably had more than his share. But he is in the middle of one more first right now, and who the hell cares if it cost him 10 million bucks to get here?

Finally, the bell pulls Jess from his flash of reverie. The gates spring open, and he leans forward in unconscious imitation as Rachel sprints in that light-footed gait of hers, flying into first place, barely seeming to touch the turf as she sets the pace, even though she has to run so much farther than all the other horses just to get to the rail. Yet there she is, first after a furlong. It is the hardest way to win a race from post to finish—to be the pursued rather than the pursuer. But that is Rachel's way, and whether she wins or loses, this is what Jess loves best about her. There for all to see is a style that holds nothing back and contains no artifice, the best and simplest and purest sort of challenge, not just in racing, as Jess sees it, but in business and life as well: catch me if you can.

Chapter 1

Diving In

Jess Jackson wriggled into his half-wetsuit, threw on an air tank, regulator, and mask, and plunged into the vineyard's dark reservoir. The icy water burned his exposed arms and legs. He could see nothing under the surface; dawn was still hours away. He'd have to feel along the slimy bottom of the pond until he found the weeds and algae clogging the irrigation pumps, then rip them loose so that the reservoir waters could once again flow to the vines.

His big hands reduced to clumsy clubs by the cold, he tried not to panic as he felt around with numbed fingers. He knew time was not on his side. The banks of drippers and sprayers in the fields could protect the grapes from fatal frost. Liquid water soon froze once sprayed on the vines, but that was good: it insulated the fragile fruit, forming a barrier between the grapes and the much colder air temperature that would burn and ruin the crop. But the vital pumps had clogged, the protective waters were not flowing, and there was no one but this middle-aged lawyer and part-time vintner there to do something about the incessant frost alarm. Jackson knew he either could complete this crazy, bone-chilling dive, risking possible hypothermia to save his fledgling vineyard, or he could walk away, go sit by the fire, and lose the farm in a matter of hours. As in, literally lose the farm.

In truth, this wasn't much of a debate for Jackson. In a crisis he preferred offense to defense whatever the consequences—punching rather than rolling with the punches. His years working as a policeman, an ambulance driver, a lumberjack, a gambler, and assorted other risky and dicey careers had convinced him of that much. Years later that résumé would make him a unique entry on Forbes's list of the world's wealthiest men. Not too many former Berkeley cops joined that rarefied company—just one, in fact. So he had raced to rummage through the storeroom where he had stashed the family's sporting gear in old wine barrels. He tore through the tennis rackets, golf clubs, and old volleyballs and finally came up with his diving rig. No one else in the family had been quite sure why he had hauled all this junk up to the farm. Now it seemed there had been a method to the madness as he told his wide-eyed daughter, "I'm going in."

Such was life on Jess Jackson's first mountain. This was long before he acquired another, gentler mountain in Sonoma Valley Wine Country: his prized high ground for the empire he would build of wine, real estate, and horses. But that first freezing, dying, water-starved vineyard was something very different, more trial than trophy. This weekend retreat sat high up in Lakeport, California, a winding, precarious drive three hours north of the house in the San Francisco Bay Area. This property, too, was fertile and beautiful if he squinted hard, but it was also rugged and unforgiving: steamy in summer, achingly cold in winter, the kind of land that looked back at a farmer and dared him to plant. This was not the fashionable, pricey verdancy of Napa and Sonoma to the south, but a far more difficult landscape to tame, a bigger risk, on the far edge of what could reasonably be called California Wine County. It seemed a long-shot start for what would soon be America's most popular wine and one of the country's most successful entrepreneurs—if he survived that cold, dark plunge.

An hour later Jackson staggered out of his black lagoon, and soon enough the pumps were chugging away, the grape harvest had been saved, and Jackson sat wrapped in blankets in the living room as his daughter ferried him mugs of hot tea. Two hours passed before he stopped shaking. This gave him plenty of time to think, to take stock, to realize what an idiot he had been. Hunched there, the warmth slowly returning to his chilled limbs, he couldn't stop thinking that he had taken a very big risk for precious little.

He had been growing grapes for a few years by then, selling the harvest to wineries that always needed extra fruit to round out their crush. This had started out as a nice little sideline to his busy law practice. He wasn't contributing to world-class wine or anything close. But he had wanted to teach his two daughters how to farm, and they had worked hard. They had planted all sorts of veggies, too, along with the grapes and the walnuts. Now in his fifties, the workaholic lawyer could almost imagine a Lakeport retirement in the not-too-distant future. He had found a property that offered him a taste of the farming he had grown up loving and respecting in a way only someone who had known the Depression and poverty could understand: the idea, almost a genetic memory as he imagined it, lodged deep in the human DNA, that if you had a bit of land and could grow a crop, then you'd always be able to put food on the table no matter what else happened. "I'm happiest when I have a lump of dirt in my hand or animals to tend," he told his children more than once—the two he had at the time, as well as the three who would come much later, and then the grandkids, too.

But that wasn't what was going on up in Lakeport by then. Ambition and necessity had gradually tractored over the simple joy of cultivating the earth, of raising a delicate, flavorful tomato that no one would confuse with supermarket fare. He had planted more grapevines, upping his harvest year after year, until the hobby days were over and he needed the grapes to pay their way. Instead, he was getting next to nothing as the once lucrative seller's market for wine grapes had predictably become a buyer's market because everyone had overplanted. Now he was in the no-man's-land between hobby and full-on business—and a failing business at that. Something had to change.

Even though Jackson couldn't have fully articulated it at the time, this moment of desperation and ridiculous stomping around in a wetsuit would mark a turning point, a milestone, and not just for Jackson and the company he was about to create. He would help drive the transformation of the entire sprawling California Wine Country from a sleeping, laughable giant—whose most popular products at the time included $3 strawberry wine that tasted like cough medicine—into what it is today: the center of America's $30 billion wine industry, envy of the world. Jackson would be one of a handful of winemaking pioneers who led this transition, and it happened because this was the moment when he decided it might be time to gamble on a new way of doing business. Why should he sell his grapes to someone else? Why not begin to make his own wine? Why not build his own winery? If he was going to freeze his ass off to save a vineyard and sit shaking and blue by the fire in the middle of the night, he didn't want to do it so that someone else could make wine that came in boxes. Maybe he could make something great, something to be proud of, something that would endure. And a half-formed vision came to him of having a sprawling winery, of growing grapes here and around the state, of amassing bits and pieces of the old estate vineyards that had flourished early in the century, declined during Prohibition, and were now ripe for the taking. This picture made perfect sense to him, though he was at that moment in 1980 just a lawyer with chattering teeth, a few acres of grapes, absolutely no idea how to make great wine, and no previous desire to be a winemaker. But he felt fate had sent him a message: Why not go big, risk everything, try to make something unique and delicious, and see what happens next?

The vision was foolish, impossible, and brilliant, for out of such unlikely dreams an empire arose. Jess Jackson, who had been speaking with his wife, Jane, about retiring from the law and taking it easy, of slowing down and enjoying life, was about to embark on one of the greatest reinventions in American business history. It would take another disaster to finally push him over the edge that divided dreaming from action, but once he did, he would go on to put Chardonnay on America's tables (a wine then barely known to the American public) and make the most popular version of it in the United States for more than a quarter century running. He'd help propel California wines from tasting-room backwaters to world-class vintages, expanding his little wine company's reach from one in which he was CEO, chief counsel, and door-to-door salesman into a global concern making and selling wine on four continents. Yet he would retain the practices and values (and iron control) of a small family business, right down to the traditional handcrafted oak barrels that other global brands abandoned for the sake of efficiency and economy.

And when wine had made him a billionaire several times over, he reinvented himself again as a thoroughbred horseman, rising from the bottom to the top of that bruising business, too, as he moved in the space of a few years from easy mark for con artists to owner of the horse of the year three years in a row.

His decisions and the hard-nosed inspiration that followed that frigid night of the clogged reservoir would make him a leader for the wine industry, regularly emulated and envied because, even his bitterest rivals would concede, he so often seemed to be ahead of the curve. His moves changed the world. Those same moves would also destroy his first marriage, alienate his eldest daughters, drive him repeatedly to the brink of bankruptcy even as he remarried and raised another three children, and embroil him in battles, vendettas, epic lawsuits, and corruption investigations involving some of the most powerful players in wine and horses. And beyond that swirl of events and turmoil, Jackson would end up building something he felt certain would endure: a family business designed to thrive for generations. He longed to make something akin to the great winemaking dynasties of Europe, the Antinoris and the Frescobaldis, who for centuries have passed on the tradition and culture and ancient bonds of the grape, a beverage Jackson saw as unique in symbolism and significance, as old as civilization itself. In the decades that followed that frigid predawn dive, he could have sold out a dozen times over at immense profit to the megacorporations that control most of the rest of the wine industry. Everyone else did: the Fetzers and Mondavis, the family wineries that are now just labels on a corporate spreadsheet. His Kendall-Jackson dynasty is the last of them left standing, a man and his mountain.

He accomplished all of this, for good and ill, after age fifty, one of the greatest second acts in the history of American entrepreneurship.

Chapter 2

First Pour: Glut and Stuck

When Jess and Jane Jackson bought the old farm in Lakeport, it was supposed to be his getaway, his career extender. The old pear-and-walnut orchard on the northern edge of Wine Country would, Jess vowed, allow him some breathing space from the San Francisco law practice. It would be his respite from the pressure of managing a busy firm and litigating the high-stakes real estate cases in his esoteric specialty of inverse condemnations. This was a type of law that few knew well but that was in high demand in the seventies, as newly (and belatedly) environmentally conscious state and federal governments were rushing to convert unique coastal properties into parks and preserves before all of California could be paved over. Jackson had no problem with preserving the state's most valuable and fast-disappearing natural resources. In fact, he applauded it, and earlier in his legal career he had even worked the other side. One of his first jobs out of law school had him representing California as it scooped up properties and rights-of-way in the fifties and sixties, though his work then was more about preserving space for freeways than for parks. Now, however, he worked to make sure his clients—mainly large landowners and developers—got maximum compensation for being told their plans to build yet more ocean-view resorts, shopping malls, and subdivisions would have to give way to the occasional national seashore or coastal forest preserve.