A few days after Christmas, G. Brint Ryan stood in the lobby of the Hotel Settles, in downtown Big Spring, and watched intently as a flurry of workers hustled around him. He wore a pair of shiny black boots and a mohair jacket, and his youthful face was punctuated by a piercing gaze that seemed to suggest that time was wasting. The workers in the room kept their heads down and avoided eye contact.

Although Ryan, who is 49, had grown up in Big Spring, few locals knew who he was until several years ago. Like so many others raised in the gritty West Texas oil patch, he’d taken what ambition he possessed as a young man and hightailed it out, ending up in Dallas, where he had built one of the most powerful corporate tax consulting firms in the world—called, simply, Ryan. Located on four continents, the company wrangled and litigated more than $1 billion dollars each year in overpaid taxes from local governments for a slate of global Fortune 500 clients, including Walmart, Tyson Foods, and ExxonMobil. 

Along the way, Ryan had acquired a high profile, at least in Dallas. Known primarily as an extremely aggressive CEO, he’d also waded into politics, waging a brutal—and ultimately futile—million-dollar campaign for city council in 2009. He spent millions in personal campaign contributions to favored candidates; kept current and former lawmakers (including former comptroller John Sharp) on his payroll; threw fundraisers for his buddy Rick Perry at his $10 million Preston Hollow estate, where the back terrace featured life-size bronze statues of Ryan’s five daughters; and let’s not forget the speeding tickets he received for racing his Lamborghini Gallardo down the Dallas freeways. But Ryan’s greatest impact was through the work of his firm, whose reverse audits routinely yanked hundreds of millions of dollars from the state treasury. 

Back in Big Spring, it was a different story. Some locals remembered his family, who had arrived as pioneers in the nineteenth century. But Ryan himself was mostly a mystery, a native son who had been gone 24 years when he showed up in 2006, all but promising to raise the dead. He had just purchased the Hotel Settles, a decrepit landmark whose life and death had more or less coincided with the rise and fall of this once vital “Crossroads of the West.” The fifteen-story art deco hotel had been built in 1930 as a totem to Big Spring’s first oil bonanza. When it was finished, the Settles was hailed as the tallest building between Fort Worth and El Paso, and certainly the most luxurious. It became the cornerstone of local society and a major attraction along the cross-country Bankhead Highway (U.S. 80) and the Texas & Pacific Railroad, with a guest list including Herbert Hoover and Elvis Presley. 

This was, of course, a different time, a time before the center of gravity shifted from Texas’ small towns to its big cities, a time when grand hotels like the Settles, or the Baker, in Mineral Wells, were full of glamour, a time when it was possible to start a business and make a living on the bustling downtown streets of a place like Big Spring, before the interstates and the shopping malls and the fickleness of fleeting industry took it all away.

The Settles closed in 1980, joining the drugstores and dress shops that had begun to vanish after the local air base closed. It sat empty for almost thirty years, deteriorating almost to the point of total ruin. There were many attempts to restore the old dame, but all of them failed, and eventually the Settles became nothing more than an investment quagmire, a fifteen-story corpse telegraphing decay. Town leaders hoped it would simply fall down. There was talk of persuading a Hollywood production company to come blow it up for a movie. 

So when Ryan showed up vowing to bring it back to life, more than a few locals wrote him off as just rich and insane. And they remained skeptical, right up until the moment, last December, when the hotel was miraculously reopened, impeccably restored. For weeks afterward, passersby gazed up at the glowing sign and the beautiful facade. “How could this have happened?” they wondered. “And what else might happen now?” Could the Settles, having stood for so long as a symbol of Big Spring’s decline, now embody its unlikely resurgence? Ryan seemed to think so. “If we can do what we’ve done here,” he explained to a reporter on the afternoon of the grand opening, “tell me what project in Big Spring cannot be done.” Which seemed to suggest that one of the West’s great boomtowns had found its latest dreamer.

IN AUGUST 1881 AN UNUSUAL FIGURE STEPPED OFF THE train outside Big Spring, dressed in gray corduroy, despite the summer heat, and wearing a cravat. Heneage Finch, the Seventh Earl of Aylesford, had fled England to escape a public scandal involving his adulterous wife and had headed west for an extensive lost weekend. Shortly after arriving, Finch was reciting his distinguished lineage to a bartender in nearby Colorado City when the barkeep cut him short, saying, “Look here, Earl, all that stuff won’t go down here. We’ll just call you Judge, and that way nobody will get hurt.” The Englishman received a $50,000-a-year allowance from his family, enough to build a “modest castle on the prairie,” in the words of one reporter. For the next four years, the Judge traveled extensively around the region, shooting wild turkey and antelope and buying copious rounds of drinks for any cowhand who would let him. Said to consume several quarts of whiskey and gin a day, by 1885 the Judge had managed to drown more than just his broken heart. One afternoon at the Cosmopolitan Hotel, where he’d since relocated, the Judge calmly stood up from a card game, said, “Goodbye, boys,” to the friends seated around the table, then crawled into bed and died.  

The Judge is now ingrained in local lore, in part because he is perfectly emblematic of a certain kind of outsized character that, throughout the years, has been drawn to Big Spring. Thanks to its geographic position atop massive oil reserves in the Permian Basin, the town has never wanted for schemers, visionaries, or millionaires promising the sky. Consider S. E. J. Cox, an unknown oilman who walked into the Big Spring Commercial Club in 1919 and demanded drilling leases on 200,000 acres under which his “doodlebugs” had indicated a sea of crude. Cox drilled eight wells and only one of them struck, on the McDowell Ranch, seventeen miles south of town, but it was enough to spark a craze. He planned a grand celebration to showcase the well, inviting 10,000 potential investors, who arrived from as far away as New York, Hawaii, and New Zealand. At the time, Big Spring had around 4,000 residents, but there were so many guests that refrigerated railcars were brought in, packed with 100 beeves and 60 muttons to feed the large crowd. According to the Big Spring Herald, the festivities were kicked off by a local cowboy who appeared overhead “riding” Cox’s single-engine plane, “perched on a saddle in front of the tail and blazing away with his six-shooter.” 

“Behold this black gold you see flowing,” proclaimed Cox with a wave of his hand. “This black gold is a messenger of a new day in Big Spring and West Texas.” Sadly for Cox, the well never really produced. But his discovery was enough to keep people drilling, and in 1927 the big boom finally hit, prompting thousands more to pour into Big Spring looking to get rich. 

W. R. Settles was not one of them. The local cattle rancher was a simple man, and even after a gusher was tapped on his ranch, he remained the modest and devout Presbyterian he’d always been. But after donating the proceeds of his first well to his church, Settles was bombarded with myriad suggestions of what to do with his money. With Big Spring’s population in the process of tripling, hotels were very much in demand. Local leaders convinced Settles to build not only a new hotel for the expanding city but one that would dwarf all others. 

A prime downtown location was chosen, along with a famed West Texas architect, David S. Castle, and after a lightning-fast year of construction, the hotel opened on October 1, 1930. No expense had been spared. The cost of the hotel, plus furnishings, ran to $700,000, almost equal in value to all the building permits issued in Big Spring that year. A spectacular marble staircase rose from the lobby and split in two directions toward the mezzanine and the grand ballroom. The floors were polished maple, the paneling was mahogany, and the furnishings were the finest walnut. According to a special section on the hotel published by the Herald, the 170 rooms featured “running ice water” and luxury bathrooms decorated in “Egyptian color schemes of black and white.” An eleven-piece orchestra provided entertainment, with more than three hundred people packed into the ballroom each night. 

Fred W. Crow, the hotel’s manager, told the Herald, “I have no hesitancy of comparing the class, service and beauty of the Settles Hotel with that of the New Yorker in New York City. In fact, I think this hotel is superior in many respects.” 

But Settles was not able to enjoy it for long. By the time his hotel opened, the Great Depression had struck. The lavish construction budget had left him vulnerable, and by June 1932, he had lost everything. Settles lived out the rest of his days in a modest house in town, but the hotel survived under new ownership and even emerged as one of the few local bright spots as the Depression dragged on. Traveling big-band orchestras played the ballroom nightly before crowds decked out in ball gowns, tuxedos, and top hats. “They just don’t throw parties the way they used to at the Settles,” the humorist Will Rogers once reportedly said. The most popular band to play the Settles was led by a young Lawrence Welk, who was a fixture for several years. And people still talk about the day in February 1935 when former president Herbert Hoover and his son, Allan, stopped in for a lunch of fried eggs and hash, interrupting the Luncheon Club’s weekly bridge game. 

The Second World War finally pulled Big Spring out of its slump. In 1942 the Big Spring Army Air Field (later renamed Webb Air Force Base) began training bombardiers, which meant three thousand cadets and a flood of money. When victory was declared over Japan, soldiers staying at the Settles ripped it apart in drunken revelry, slashing pillows and hurling furniture onto the sidewalk. A naked lady was seen being dangled out one of the windows by her feet. After the war, the airfield continued to thrive, and the local Cosden Petroleum Corporation enjoyed an upsurge supplying aviation fuel to a new war in Korea. With both the base and the refinery, Big Spring supported a substantial upper class, whose clubs and societies brought celebrities and dignitaries through the Settles at a regular clip. 

The fifties were golden years for the hotel. Big Spring’s population soared to 30,000. Downtown became so busy that it sometimes took on the feel of a circus. One afternoon in 1953, a crowd gathered outside the Settles to watch  Benny and Betty Fox, two professional acrobats, dancing the Charleston on an eighteen-inch platform extended from the hotel’s fourteenth floor for a touring act called “The Dance of Death.” 

The wonder years, however, were short-lived. In the following decade, the town began its decline. In March 1967 the T&P took its last passenger from the Big Spring depot, ending service after 86 years. Interstate 20 had just been completed, allowing traffic to bypass the Bankhead Highway around the northern edge of town. Shortly thereafter, a Holiday Inn and a Ramada Inn appeared along the new exits. By then, the Settles was on its last legs. In May 1969 the hotel enjoyed a final hurrah with the release of the Academy Award–winning film Midnight Cowboy, the opening montage of which had been filmed downtown. In the scene, Joe Buck, played by Jon Voight, quits a dishwashing job at Miller’s Restaurant and catches a bus for New York City to seek his fortune (which would involve, many locals were later scandalized to find out, male prostitution). The camera pans out as the bus pulls away, and the Settles is seen fading into the background. 

By 1975, the hotel was rarely booked and had gained a reputation as a flophouse and a brothel. The final blows, for both the hotel and the town, came at the end of the decade. Webb Air Force Base was decommissioned, wiping out nearly three thousand jobs, and Cosden was acquired and its executives relocated to Dallas, yanking away much of Big Spring’s upper class. The Settles, no longer deemed viable as a hotel, was put up for sale. New owners wanted to convert it into apartments, but the plan never got off the ground. In May 1980 they cut the power and shut the doors. Workers arrived to strip away the hotel’s vintage furnishings, the ones that W. R. Settles had mortgaged his ranch to pay for. They pried away the mahogany paneling and marble stairs and dismantled the wrought-iron railing. Everything that could be removed—beds, stoves, telephone booths, doorknobs, room keys, even the plumbing inside the walls—was carted out and sold at auction. Once a symbol of Big Spring’s soaring ambition, the Settles was reduced to an empty, naked shell. 

THE YEAR THE HOTEL closed, Brint Ryan was a sophomore at Big Spring High School. He’d been inside the hotel only once, with his grandfather, to sneak a peek at the lobby. Ryan and his family lived fifteen miles north of town, on the same section of farmland that his great-grandfather Jesse Brinton Ryan had acquired in the early 1900’s. One of the first pioneers of Big Spring, Jesse had arrived in 1887 from Pennsylvania, seeking a job and adventure. For years he worked as a locomotive fireman before marrying and settling down to farm the red soil—as did his son, Ryan’s grandfather. Ryan’s father, George Alden Ryan, broke with family tradition and went to work in the gas plant in Vealmoor. He married his wife, Virginia, fresh out of high school, when she was just seventeen, and had four kids, of whom Brint was the oldest. Virginia was ambitious by nature, but a houseful of kids afforded her little mobility. She helped keep the family afloat by selling insurance, but it was seldom enough. Her and George’s arguments over money were epic and frequent. 

“Ever since the day I was cognizant to when I was an adult, I’d seen them struggle,” said Ryan. “If it weren’t for both sets of their parents, we’d have never made it in those days.” 

At school Ryan was a diligent student. He played trombone in the high school marching band and sacked groceries at the Safeway in College Park. Senior year, he was voted class president. When he graduated, in 1982, Big Spring was experiencing a small oil boom, but it wasn’t enough to keep him around. Although most of Ryan’s friends had enrolled at Texas Tech, he chose the University of North Texas, in Denton, intending to put as much distance between him and his hometown as possible. Years later, Ryan would show his father a check from one of his clients, an oil company. “It was for $3.2 million, and it was more money than he’d made his entire life,” he said. “For me, theirs was not a standard of living that I was interested in at all.”

In 1986, while Ryan was starting graduate school, his parents divorced. George stayed on the homestead and Virginia moved to town, where she took over her father’s insurance business. It was a new start for Virginia, but not long after her new life had begun, a tragedy ended it. One night in December 1989, she went out driving with a man she was dating. According to Ryan, the man was drunk, and at some point his mother attempted to exit the vehicle. “She tried to get out,” he said, “and he basically ran over her.” 

At the time, Ryan was 25 and living in Dallas, working his first year at Coopers & Lybrand (now PricewaterhouseCoopers) as a public accountant. He returned home to bury his mother, settle her affairs, and help prosecute the case against her boyfriend. His father moved to town with Ryan’s two younger brothers, and Ryan packed up the homestead and sold it off (he later bought it back). “It was the fruit-basket turnover in my life,” Ryan recalled. “I went back to Dallas after the accident and worked a couple more years at Coopers, then left to start the company I run today. For fifteen years I kept my head down and I didn’t think about Big Spring. It was not a place I looked back on fondly.” 

Ryan started his company in 1991 as a modest CPA firm with five employees and $156,000 in revenues. He ran it like a “sweatshop,” he later told Smart Business, with a mandatory 55-hour workweek. “People wore the amount of hours they worked like a badge of honor,” he said. “It was very inflexible.” 

Early on, he was notorious for his temper and pit-bull tenacity, especially when dealing with the taxing authority. In 1994 he barged into the state comptroller’s office, then occupied by John Sharp, raving about a rule change that had cost one of his clients dearly. “The change was wrongheaded,” said Ryan. “I was pretty aggressive.” Somewhere during his protest, he said, Sharp “abruptly showed me the door.” In later years, he would sue the head of the IRS, along with treasury secretary Timothy Geithner. According to the New York Times, Ryan even sued one of his own clients, Advanced Micro Devices, when they declined to pursue $30 million in tax savings. It wasn’t just that Ryan’s firm would lose the commission on the winnings (around 30 percent); there was something more. “It’s like he takes it personally,” said Sharp. 

The firm eventually shifted to corporate consulting, specializing in the lucrative trade of refund claims and reverse audits. In 2006, in one of its most public cases, the company won back $128 million in overpaid state taxes for Texas Instruments. Meanwhile,the firm’s incentives program—although constituting less than 10 percent of its earnings, according to Ryan—had become the most powerful in the state. Brokering massive tax breaks for some of the world’s largest corporations, especially if they agreed to do business in Texas, had given Ryan incredible influence in Austin. 

Last December, the Times reported that ExxonMobil and Raytheon had secured tens of millions each in refunds thanks to Ryan, who had also won incentives for Samsung and many others. The article also raised a question about the “hefty discounts” the state gave to such corporations on their school tax bills (many of the deals arranged by firms such as Ryan), while cutting education spending during the last legislative session by $5.4 billion. And it suggested an unusual conflict of interest in awarding that money: Over the years, Ryan had donated hundreds of thousands to the campaigns of the last two comptrollers. He’d served as chief fund-raiser for Governor Perry’s presidential PAC, Make Us Great Again, and belonged to the group TexasOne, which recommended possible companies for the governor to recruit for relocation to Texas with “enterprise zone” tax credits; of those offered incentives, more than a third were Ryan’s clients. His payroll included a state House representative tasked with helping draft tax policy. Ryan had even hired Sharp after he left the comptroller’s office, and Sharp had remained with the firm despite being appointed by the governor to lead a commission that recommended changes to the state’s tax system (though as Sharp noted, “The tax changes I recommended resulted in a large tax increase for Ryan Inc.”). Most recently, the article noted, Ryan had been appointed to a commission created by the Legislature to assess, among other things, the state’s cash grants to companies. The appointment had come from Lieutenant Governor David Dewhurst, to whom he’d given more than $150,000 in campaign contributions.

When the Times article ran, Ryan was furious, saying the reporter had mangled the numbers: “She came to the table with an agenda that economic development is a bad thing. She twisted the facts and my personal circumstances to support the outcome of her story.” Later, he acknowledged instances of having saved clients “ten times or more the amounts reported in the New York Times, but those are unusual matters.” What wasn’t unusual was for Ryan to catch that kind of heat, and deep down, he probably welcomed the fight. After all, one of Ryan’s favorite quotes was from Teddy Roosevelt’s oft-referenced “man in the arena” speech, which dismissed critics as “cold and timid souls who neither know victory nor defeat.” One got a sense that at the end of the day, when Brint Ryan looked out toward Dallas from his top-floor suite, he envisioned himself as that man, whose face was “marred by dust and sweat and blood, who strives valiantly.”

BACK IN BIG SPRING, Tommy Churchwell would often catch himself driving slowly past the Settles. Churchwell was a sentimental insurance agent with a thing for old buildings. On family vacations to New York City, he’d march his kids around Midtown, stopping in at St. Patrick’s Cathedral or the Flatiron Building. “They know how to keep those buildings preserved,” he said. “And I never knew why someone couldn’t do that with the Settles.”  

After being stripped clean, the hotel had changed hands two more times, finally ending up with a San Antonio developer who promised to turn it into luxury apartments. But he spent five years mired in tax and legal troubles, while nature and vandals further desecrated the hotel’s interior. A popular Friday-night pastime was to climb to the roof of the Settles, pry the heavy capstones from the parapet, and hurl them off the tower. The boulder-size blocks, in addition to iron radiators torn from the rooms, would crash through the roof and ceiling, bounce off the mezzanine, and then land in the lobby where they would shatter the terrazzo floor. Pigeons followed, as did the rain, which flooded the lobby and melted away the ornate decorative plaster.

When the city of Big Spring foreclosed on the property in the early nineties, the local economy was at rock bottom. Downtown was essentially abandoned. The hotel was a ruin. A ferocious hailstorm had broken the remaining windows, and curtains flapped in the wind. As city manager Gary Fuqua put it, “The Settles had become a monument to Big Spring’s failure.”  

By 1995, residents had grown so frustrated by the eyesore on the northern skyline that many were calling for its demolition.  Churchwell knew he had to act. “People didn’t realize that when that hotel was gone, our identity as a town would go with it.” He figured that until it could be restored, it could at least be spruced up, so he organized a group called Friends of the Settles and began a campaign to replace the hundreds of broken windows with tinted storm glass. Residents could buy a new window for $150. By 1999, the group had managed to sell more than three hundred. “It made people realize its potential, how beautiful it could look,” said Churchwell. But windows were all anyone could afford. After a while, the excitement began to fade. “People went their way, and we waited,” he said. “And then, out of nowhere, here comes Brint Ryan.” 

In 2006 Ryan received a phone call from an old classmate named Troy Tompkins, who was then on the Big Spring City Council. A developer named Ralph Mahoney was interested in purchasing options on a number of buildings downtown with plans for a kind of entertainment quarter, much like Lubbock’s Depot District. Mahoney needed tax advice, and Tompkins figured his old friend Ryan could come to town and help out. 

Though it had been more than two decades since Ryan had really spent any time in Big Spring, he wasn’t so determined to see it in his rearview mirror anymore. When Mahoney spread out the maps for his proposed entertainment district, Ryan noticed a glaring omission. “What about the Settles?” he asked. The answer was that it was impossible to tackle. Ryan asked for a tour anyway, and a few weeks later, he and Tompkins were standing in the lobby amid a scene of sheer destruction. Sunlight poured through the ceiling. Mounds of debris covered the ground, two and three feet deep along the upper floors. The basement was full of water that bubbled up like a geyser with every big storm, depositing giant dunes of fine, red sand. Both elevator shafts were filled with nine solid feet of asbestos, which had previously been stripped and dumped there. 

“The problem wasn’t even the asbestos,” remembered Tompkins, “but the piles of dead pigeons and dried feces.”

At the end of the tour, the men made their way to the roof and stepped out onto the deck. From there, they could see the craggy hills of the Caprock rolling and tumbling into the Staked Plains. The old Cosden refinery (now operated by Alon USA) sparkled under the sun. “When I saw the community from that vantage point,” said Ryan, “I knew I had to do it. I was hooked.” 

That year, a couple of days before Christmas, Ryan gathered his family at a restaurant in the Galleria in Dallas. His siblings, his father, and his new stepmother were all there. As they sat around the table, Ryan announced his plan to renovate and reopen the Settles. His brother Kris scoffed at the idea. Unlike his older brother, who was cosmopolitan and polished by years of corporate culture, Kris was pure Big Spring, from his slow drawl down to his well-worn boots. At the time, he was single and living in Denton, where he’d studied accounting. He was working for an e-commerce firm, drinking too much, and generally refusing to grow up. The death of their mother had left the brothers estranged. “I was eight when he graduated and left for school, and he never really came back,” said Kris. “He was always doing bigger and better things. But Brint wouldn’t be where he’s at if he was screwing off like I was. When I was eighteen years old, all I wanted to do was drink beer.” 

At the dinner table that Christmas, Kris told Ryan that he’d lost his mind. “If you’re looking to throw money away,” he said, “I got some pockets you can start with.” Ryan did better than that. He made Kris the general manager of the entire operation. The following month, Kris moved back home to Big Spring.  

“Knowing how to build a business is one of the most valuable skills anyone can possess,” Ryan said. “And I wanted my brother to learn it—not incrementally but instantaneously, by throwing him into a very difficult situation. I knew he’d either sink or swim.” 

The idea Ryan pitched to the family, and later to Big Spring, was to renovate the Settles as a combination hotel and residential and commercial property. Because of the degree of damage to the interior, Ryan figured he would have to spend around $12 million. The appraiser he hired before buying the property (for a meager $75,000) estimated the building’s value at negative $250,000. 

There were two significant differences between Ryan and the others who’d tried to save the Settles. First of all, he was not just rich; he was extremely rich and would be starting with zero debt. Second, whether because Big Spring was his hometown or because he knew he could afford it, Ryan didn’t seem at all afraid of losing every last cent. “The premise for all those other deals was investment,” he said. “Someone wanted to take the building, write a check, and make money. I knew that was unlikely. I didn’t intend to make money. I wanted to return this great landmark to the city.”

Having spent his career finding advantages in the tax code, Ryan was also uniquely prepared to exploit every possible exemption for his new project. By the time he was finished, he had secured $7 million in federal New Markets Tax Credits, which go to help businesses in economically depressed areas, and managed to get his hotel included in the National Register of Historic Places—which qualified it for $5.2 million more. He’d also insisted the city put some skin in the game, arguing that much of the hotel’s water damage had occurred under its ownership. Despite a terrible economy at the time, and against the protest of many residents, Big Spring’s economic development board gave Ryan another $3 million. 

Meanwhile, Ryan was buying up other properties downtown, including the old bus depot down the block and the Ritz movie theater on Main Street, one of Big Spring’s great Spanish colonial gems (Ryan now owns four city blocks). And when it came time to start on the Settles, on August 21, 2008, he arranged for an impressive display of power, bringing in various lawmakers whom he’d worked with over the years, including Sharp and Perry. “That was one of the proudest days of his life,” Sharp said. “That hotel was like a new baby.” 

After spiking the ground with a gold-plated shovel, Perry addressed the crowd, noting that as a child growing up in nearby Paint Creek, and during his time stationed at Webb, he’d always marveled at the Settles. “What this once grand building needed was a champion,” the governor said. “That champion arrived in the form of Brint Ryan.”

For the next year, a cloud of dust hung over Third Street. Workers stripped more than seven hundred tons of asbestos and debris. Using plans based on the original blueprints, they painstakingly began to reconstruct the old hotel. The original birch phone booths were recovered, along with a chandelier and pieces of the walnut furniture. The staircase’s wrought-iron railing needed rebuilding; the paneling had to be replaced. New plumbing and electrical was installed throughout. A million dollars was spent restoring the original yellow-pine window sashes. The hotel’s old neon sign—a fixture on Big Spring’s skyline for nearly half a century—was re-created, to the tune of $100,000. 

As general manager, Kris was out of his league. He’d never even stepped foot on a construction site, and now he was supervising the biggest historical renovation in Big Spring history. “He didn’t know anything,” said Dan Vander Zee, a veteran Dallas contractor who’d come on to manage the construction. “His brother had given him this enormous job, and he was completely overwhelmed. But to his credit, he put his head down and learned fast.” 

As the project progressed, Ryan kept hearing about Jeff Trigger, the undisputed guru of historic Texas hotels. Trigger had steered the renovations of the state’s most iconic luxury properties: the Mansion on Turtle Creek, the Hotel Adolphus, and the Stoneleigh, in Dallas; the Driskill, in Austin; and the St. Anthony, in San Antonio. Trigger was even in the process of taking on the resurrection of the Baker Hotel, the sprawling, palatial, possibly haunted behemoth in Mineral Wells. In addition, his company, La Corsha Hospitality Group, was behind the five-star restaurant Congress in Austin, consistently voted one of the state’s best. 

Ryan met with Trigger in 2010 and found someone who shared his penchant for going big. A busy and energetic man, Trigger is a famous stickler for detail—the kind of person who still picks up gum wrappers and straightens pictures on the walls in properties he no longer manages. After meeting with Ryan, he visited the Settles and immediately saw the potential. In addition to the hotel, the town had a nearby state park, a golf course, and the newly renovated 1,412-seat municipal auditorium, located just a block away, home to the Big Spring Symphony. Trigger drafted a pro forma that showed the hotel turning a profit in less than three years. Ryan was flabbergasted. “If you can do that,” he told him, “you’ve got a contract for life.” 

In order to make money, said Trigger, the whole vision had to change. Rather than just being refurbished, the Settles had to reclaim its crown as the finest property between Fort Worth and El Paso. It had to become a destination. What Donald Judd’s art installations had done for Marfa, the Hotel Settles would do for Big Spring. 

Under Trigger’s direction, the rooms became bigger and more upscale. By the time he finished with his plans, the budget was knocking $30 million. The grand ballroom was redone with an eye toward making it the dream of every Texas bride. A salon and spa were added, as was a swimming pool with an air-conditioned pavilion. The 130-seat Settles Grill would fill the footprint of the old coffee shop, and Trigger sent the newly hired head chef, Rob Cook, to create a menu with David Bull in the Congress kitchen. Across the hotel lobby, the Pharmacy Bar and Parlor was built in place of the old drugstore. In addition to poker tables, there would be a subterranean cigar den called the Judge’s Chamber, in tribute to the Earl of Aylesford. 

THE GRAND OPENING was scheduled for December 28, and I drove in to see it for myself. I’d spent much of my childhood in Big Spring, and I’d always known the Settles as a relic of my hometown’s better days, stories of which I’d savor at every family gathering. My cousin Homer had witnessed the daredevil performers Benny and Betty Fox while selling newspapers outside the Settles; my uncles Ed and Fred, who were twins, had worked as bellboys before the war; and as children, virtually all my aunts and uncles had ventured into that lobby pretending to be guests just for a chance to ride the bronze-plated elevators. One of my aunts had later bought new windows for the hotel from Tommy Churchwell. 

The ceremony would begin with evening cocktails in the lobby before moving outside for the lighting of the rooftop sign. A trio played jazz standards in the corner, while servers stood ready with champagne and hors d’oeuvres. As the guests arrived, most stopped short just inside the lobby and stood frozen, stunned by the majesty of the room, as if they had been taken back 82 years, to a time when the town was young and met its dark days by swinging through the night. 

Soon the room was filled with guests, including city council members, Tompkins, and, of course, Churchwell. Some local judges, dressed in boots and cowboy hats, posed for pictures near the Judge’s Chamber. And people whispered about the nine-thousand-square-foot penthouse on the fifteenth floor, reserved as Ryan’s private quarters. What sorts of tax deals would be made behind those closed doors?

Ryan soon appeared with his wife, Amanda, and their five daughters, who ranged in age from five to thirteen. His father, George, was by their side, slowed by recent poor health. And centered above the sweeping staircase, between two windows that caught the glow of a near-full moon, was a large portrait of his mother. “This is my tribute to her,” he said. He announced it was time to step outside for the lighting of the sign. “You’re gonna see something that no mere mortal has seen in over thirty years,” Ryan told the crowd. 

The newspapers and local affiliates had been plugging the event for a week, and before the party even moved outside, a giant crowd had gathered to stare up into the darkness. For blocks in every direction, families and onlookers sat in parked cars waiting to get a glimpse. As people stood shivering in a parking lot across the street, Ryan jumped atop a table and thanked them for coming, for trusting in his seemingly impossible dream. He then turned to his brother. 

In the five years since he’d arrived, Kris had grown alongside the old hotel. As Ryan had intended, Kris had learned how to run a business and manage men. He’d also given up drinking, gotten married, and had two children—a young family who’d experienced no other life than the one under the shadow of the Settles. The night may have belonged to Ryan, but everyone in Big Spring knew which man to congratulate first. 

“You outdid yourself on this, my brother,” Ryan said. “I don’t always compliment—that’s not what Daddy taught us to do. I’m good at kicking butt but not always good at complimenting. But you’ve done a wonderful job, and I thank you for that.” 

Inside the hotel, workers were stationed to light the floors one at a time, culminating with the giant Hotel Settles sign. As one floor filled with light, followed by another, the wonderment contained in the streets built like steam in a kettle, finally exploding into cheers as the red letters flashed alive and the hotel opened its eyes. A red glow washed over the faces of the crowd, signaling the return of a skyline and with it a town’s wayward soul. Back inside, Ryan proposed a toast from a perch along the grand stairwell, the same one that had carried presidents and war heroes, whores and Rotarians, and would now carry Big Spring into its new era. 

And if Ryan seemed to be smiling extra wide, it was because his hotel would have a little help in the process. As the crowd drank their champagne and nibbled on grilled trout, engineers outside Big Spring were just beginning to understand the magnitude of the newly discovered Cline Shale, thought to hold more than 30 billion barrels of recoverable oil. If that estimation was correct, the shale play could drive the largest boom in American history. Drilling companies were hiring men as fast as they could, and better yet, there wasn’t a hotel room to be found on weeknights from Odessa to Sweetwater. All across the region, men were living in trailers, even tents. At the Hampton Inn across town from the Settles, rooms were fetching as much as $239 a night. 

Trigger had recently run the numbers again and found that Ryan would achieve positive cash flow within a year. Once profits started coming in, Ryan planned to use the Settles as “the first domino in a concentric circle” to redevelop downtown. The week the hotel reopened, a report Ryan had commissioned from the Perryman Group, the influential analysis firm out of Waco, was published, showing that the Settles could be expected to lead to $16.6 million in annual economic growth, as well as 240 permanent jobs. In other words, not only would Ryan and the Hotel Settles succeed, they’d make a killing. 

“To the Settles,” Ryan said, grinning as he lifted a glass. “May it stand as a beacon for what’s possible.”