Cigar Aficionado

There must have been better places to be on a chilly Saturday evening last October than the flat expanse of Stillwater, Oklahoma, an hour's drive west of Tulsa, where an overmatched Oklahoma State University football team was playing the University of Texas, undefeated and ranked second in the nation. Dinner meant a chicken breast on a plastic plate in what is euphemistically called a luxury box, but was actually no more luxurious than a doctor's waiting room. And the chattering between ers of the two teams, themselves dressed in clashing shades of orange, was hardly scintillating.

So why was T. Boone Pickens, one of America's richest men, someone who could have been anywhere in the world (and with almost anyone in the world), positioned in his customary spot above the 50-yard line, urging on Oklahoma State as it stumbled against the Longhorns? Why had he flown in from Dallas, as he does for every OSU football home game, most of the away games, and many basketball games, too?

And what could he have been thinking before his wedding in 2005 when he made it abundantly clear to his fiancée, Madeleine Paulson—an urbane, fiercely intelligent woman who was raised in Europe and owns thoroughbred racehorses—that Oklahoma State would be his priority on fall Saturdays? Especially since she was scheduled to have one of America's top thoroughbreds, Rock Hard Ten, running in the Breeders' Cup on the day of the Texas game.

"We talked about it before the wedding," Pickens confirms. "She said, 'Boone, I'm so excited for the Breeders' Cup. I can't wait for you to get involved in horse racing and meet some of these people.' And I said, 'Wait a minute! Is that a Saturday in October?' I looked at the schedule and said, 'Sorry, honey. I'll be in Stillwater.'"

Pickens' behavior exemplifies the improbable hold that collegiate athletics has on some of America's most successful businessmen, show-business personalities, politicians and lots of other people who would seem to have better things to do with autumn weekends and winter nights than watch amateurs play football and basketball. Winning team or losing team, it hardly matters; what Pickens and others like him are doing has nothing to do with jumping on any bandwagon. "He's here every week," says David J. Schmidly, the OSU president. "We keep getting beat and he keeps coming. It gives you hope."

These men have spent some of the best years of their lives on campus, integrating themselves into the fabric of a university in a way that isn't possible with professional teams. They're as much Oklahoma State, or whatever the institution may be, as the player who has it written across his jersey.

But old college ties aren't all of it. Another OSU graduate and former football player, the highly successful auto dealer Jim Click, moved to Tucson and became a devoted backer of the University of Arizona. Or consider Sam Rechter, who owns mining and construction companies, restaurants and other businesses from Alabama to the Midwest. Rechter grew up beside the Indiana University campus in Bloomington, served as a ball boy under the great basketball coach Branch McCracken, then played at Purdue. Yet he has devoted his leisure time to University of Louisville athletics for almost four decades, since moving to Louisville for business reasons and deciding Cardinals basketball would be an enjoyable way to get integrated into the community. "Now I'm completely integrated," says Rechter. He has chaired the local airport commission, served on the visiting committee for the university's medical and engineering schools, and held many other positions in town. But he rarely misses a game.

It wouldn't have been the same with a professional team. Sure, a pro fan might feel as if he has a vested interest in his favorite franchise. He can buy season tickets, put the team's logo on his credit cards and license plates, subscribe to the newsletter. But unlike college programs, that team will have an ownership group, and unless our fan happens to be part of it, fan will be short for fantasy.

Owners and fans of pro teams have interests that ultimately diverge. Despite the team's thousands of dedicated loyalists, the Cleveland Browns blithely left for Baltimore in 1996 when a better offer presented itself. They were a business and existed—like businesses in other industries—to make money. By contrast, college teams truly represent their community. They can't move, they employ thousands of locals from laborers to executives, and—in nearly all cases—they're owned by a state, a municipality or a nonprofit governing board. Standing on the sidelines at an Arizona football game, a privileged position afforded him not because of his donations but because of the enthusiasm he shows for the school, Click might be forgiven if he considers the Wildcats his team. He has lived in Tucson and followed Arizona for decades, outlasting several athletic directors, numerous coaches and countless players.

Pro sports may seem to operate on a grander scale, what with the price for a commercial on the Super Bowl telecast and the stupendous salaries, but that isn't necessarily so. Pickens has given more than $250 million to the Oklahoma State athletic program and "I'll give a lot more," he says. (In January, Pickens gave $165 million to OSU, the largest single gift given to an NCAA sports program. Joe Jamail, perhaps America's top trial attorney, is said to have given an estimated $30 million to the University of Texas. Like Pickens, he was rewarded with a football stadium named after him.)

For $100 million down, leveraged to a multiple of 10 by a friendly banker, these men could easily buy their own sports franchises. In time, they'd get a sizable return on their investment, unlike donations to an academic institution, which get you a tax write-off and little more. From that perspective, professional sports is the far smarter way to go. But this story isn't about money. It's about love.

Ask a major contributor such as Pickens to show you his school's campus, and you'll get a man bursting with pride. This isn't because he has helped pay for it. In Oklahoma State, Pickens sees an academic institution on the rise, and his diploma—or, in other cases, the local connections—makes him a shareholder. "It's easier to raise money for a school if you're winning in football," says Pickens, who graduated from OSU in 1951 with a degree in geology. "But I don't want this school to be identified as a sports school only."

At 78, Pickens is as active as ever. After making his name by building Mesa Petroleum into the largest independent oil and gas company in America, then gaining a reputation as a corporate raider, he's now buying up water sources. One watchdog group cautions that he and his partners will soon control the pumping rights for tens of billions of gallons a year to Texas's largest metropolitan areas, which will doubtless make Pickens far wealthier than he is already.

But for all his money, Pickens hasn't created an entity bigger than himself. As his mortality looms, it makes sense that he wants to leave his mark on an institution that is likely to thrive for centuries. Americans may one day be driving electric cars and heating homes with solar power, and oil will be a distant memory on the order of steam-powered trains. But if all goes well, OSU will still be playing games at Boone Pickens Stadium—and perhaps even winning them by then.

Pickens likes to be involved in what the teams are doing. Whether it's a coach to be hired or a recruit considering the school, "I get consulted," he says. When that consultation interferes with business, business has to wait. "He'll be in his office, meeting with his investment committee, and a call will come in from someone in the OSU athletic department briefing him on something," says Jay Rosser, who handles public affairs for Pickens' BP Capital holding company. "He always takes the call."

In some psychological sense, Pickens identifies with the university. OSU isn't Texas, a perennial contender and occasional champion in most sports. It isn't even in-state rival Oklahoma, which has won seven national titles in football. Instead, it occupies roughly the same cosmic space in its endeavors that the scrappy Pickens does in the financial world. "I don't mind being the underdog," he says. "I've been there before. I've played with my back against the wall." Hearing a characterization of Oklahoma State as the striving outsider competing against the established powers, Pickens smiles. "That looks like me," he says.

Such motivations help explain why Pickens is so generous to OSU, not just with money, but time and energy, too. He enjoys seeing friends and family in his stadium box on Saturdays, but cautions that what he's doing in Stillwater isn't about a good time. "It's about fulfilling a commitment," he says. "Doing what you say you'll do. I want to establish something with the students and the alums. I want to see us be more loyal to our school."

Clearly, Oklahoma State is fortunate to have him. Yet on a lesser scale, there are Pickens types at nearly every major university, and most of the minor ones, too. Though they might not be known nationally and internationally, they're nearly always community leaders. Though few have $250 million to spend, their contributions are no less important. And their motivations are equally complex.

Without Jim Click, Arizona's athletic director Jim Livengood says, "I'm not sure we'd make it. Financially, spiritually, any other way." The son of an Altus, Oklahoma, auto dealer, Click played college football under Sammy Baugh, the legendary pro and college quarterback who briefly served as the OSU coach. He came to Tucson in 1971, a young businessman with little money but plenty of ambition, and spent his savings on a Ford dealership. "When I came here, I was 27," he says. "I didn't know anybody. The first thing I did was set up a scholarship program at the U. of A."

Since then, he has become the most visible merchant in town, from his high-energy television commercials—in which he takes a starring role—to his ubiquitous presence at galas, openings and other community events. A natural salesman, he has a smile and a friendly word for everyone. On the street, it's one wave and handshake after another. "You'd be hard-pressed to find anyone in Arizona who doesn't know Jim Click," Livengood says. "Should he want to, he could easily be the governor of Arizona."

Click's sincerity has proven terrifically lucrative. Even when the auto industry has a slump, it rarely seems to affect rapidly growing Tucson, and it almost never affects Click's two dozen dealerships. But beyond a ion for racing cars and a private plane, his lifestyle shows few of the trappings of such success. He still lives in the same comfortable but hardly grandiose house he bought three decades ago.

Instead, Click likes to give his money away. He tries to as many organizations as he can, from the Boys and Girls Club to Junior Achievement, from hospitals to charities for the homeless. "I even bought a monkey one time for a kid who was dying," he says. What they have in common is Tucson. "Tucson has been extremely good to me," he says. He wants everyone to know that he has tied his fortunes to the city.

But as much as any city of its size in the country, Tucson's fortunes are tied to its university. And because he's a fan and a former player, and because you can't plausibly walk through campus cheering on its laboratories and libraries, Click has focused on the athletic department—and more specifically the football team, though it's Lute Olson's basketball Wildcats who have staked out a permanent place in the Top 25 and won the 1997 national championship. (Click attends basketball games and is a friend and er of Olson, but says, "Basketball's been such a winning program, they've got the whole town behind them. They don't need me.")

In his office, Click has photos of himself with two presidents named Bush, one named Clinton, one named Ford, one named Reagan. His friends and associates are some of America's most successful people. Yet it takes an extraordinary occasion to make him miss a game—such as when his business partner's daughter got married last season on the same night that the Wildcats upset undefeated UCLA. When he misses a road game, he waits at the airport to greet the team plane, win or lose. "I just want to show them ," he says.

"I've seen people like this at Oklahoma, at Kansas State, everywhere I've been," says Mike Stoops, Arizona's head football coach. "With the great ones, it's not so much the money as their . You want people there through the bad times, as well as the good times. We've struggled through some excruciating games here, and Jim sees the progress. He calls me every Monday and let's me know we're doing a good job."

Click's involvement with the program has generated friendships in high places, but he doesn't request favors. He won't even offer unsolicited opinions. "He likes to be part of the process," says Livengood. "But in the 12 years I've been here with him, he has never once called and said, 'You should do this.'" Still, when Livengood was headed to Norman, Oklahoma, to interview Stoops, then an OU assistant, he asked Click to come. "I wanted him on board," Livengood says. "It's not so much that we needed his buy-in, but someone as successful as Jim can sense the drive to succeed that someone has. He understands people." It goes without saying that Click tore up his schedule on a moment's notice. He even contributed his plane.

Click's around so much that he often knows news about the Wildcats before almost anyone else. He can be counted on to keep secrets, unlike some ers, who get a kick out of being able to disseminate information as cocktail-party chatter. That only happened once with Click, and nobody could blame him for it. In 2004, he was in Phoenix attending a rally for George W. Bush. He'd been an early er of Bush and had come to know him well. At the time, the Wildcats were just completing the process of hiring a new football coach, and had managed to keep their choice confidential. Standing at the podium, Bush saw Click across the room. He called out, "Hey, Click, who's your new football coach?"

"I can't tell you, Mr. President," Click responded. "Well, come up and whisper in my ear."

Click dutifully mounted the podium. "It's Mike Stoops," he told Bush. "We're hiring Stoops." Bush approached the microphone with a mischievous grin. "Click says it's Stoops," he called out to Click's dismay.

The next day, senior associate athletic director Chris del Conte received a phone call from Arturo Moreno. The owner of baseball's Los Angeles Angels and another big Wildcats er, Moreno had also attended the fund-raiser. Now he was calling, only half in jest, to find out why Click had known the identity of the next coach and he hadn't.

"I hear you're hiring Stoops," he said.

"How'd you find out?" del Conte asked.

"Aw," Moreno said, "Click told the President."

So far, we've avoided the word booster, a staple of salacious headlines and NCAA investigations. To the casual fan, boosters are shady operators bearing envelopes stuffed with money, looking to entice some prep phenom to attend State U. But the likes of Pickens and Click—and, on a more distant level, Kentucky's Ashley Judd, Notre Dame's Regis Philbin, Temple's Bill Cosby and other big-name ers—are boosters, too. "I'm proud to be called a booster," says Louisville's Sam Rechter. "That's what I am."

Coaches understand the dichotomy. "The worst type of booster is the guy who wants to meet players," says Louisville basketball coach Rick Pitino, who has experienced the good and the bad while coaching at Boston University, Providence and Kentucky, and as a player at Massachusetts. In Rechter, he believes he has one of the best. "He never interferes, never second-guesses," Pitino says. "He's in the background, there to the program whenever you need him. He's not interested in spending time with players."

"Being 'in the know' is not important to me," Rechter confirms. "Being a part of making something happen is." From the rear of the 12-seat section attached to his Freedom Hall luxury box, Rechter rarely raises his voice. He's not the type to jump to his feet in protest or raise a fist in jubilation. He's a student of the game, eager to appreciate a well-executed zone trap or a perfectly timed backdoor cut. That said, he'd rather see Louisville play sloppy and win than lose a classic at the buzzer. "I'm a fan of basketball, but I'm a Louisville fan," he says. "I've got a connection with this program that pro sports fans will never have with their teams. It's a touchy-feely connection that has nothing to do with being an owner."

In 1967, Rechter was a 35-year-old with four small children when he moved from Chicago to Louisville, a city he barely knew. He owned and ran the family mining and construction business with his two brothers. Future NBA pros Wes Unseld and Butch Beard were playing for the Cardinals, and Denny Crum would soon begin a three-decade coaching run. Rechter re sitting high above the court in the old Freedom Hall, the only seats he could afford. His wife, Bonnie, is a former basketball cheerleader, and Cardinals games were their splurge. "We adopted Louisville as our school, since that's where we were living," he says. "We'd get a babysitter and come to the games."

His father, who'd loved college sports, died in a plane crash when Rechter was 14. Rechter turned to basketball for both solace and a father figure. Getting connected to Louisville reminded him of who he was, and where he'd been. And he was gratified that Louisville seemed to need him. "There's usually a need on the part of an athletic department," he says. "More often than not, it isn't a financial need. Which is rather surprising to most of my friends, who figure my connection is only about giving money."

Rechter became close to Crum and watched him win national championships in 1980 and 1986. He started getting named to various committees. And when a new athletic director decided it was time for Crum to retire, Rechter lent his private plane to fetch Pitino for an interview.

These days, his mining and construction business comprises 45 stone quarries in six states and 48 asphalt plants, and he builds highways and bridges from Alabama to Indiana. Beyond that, he own businesses in an array of industries, from gas exploration to zinc dust to music (Rechter's a partner in a Louisville jazz club). One of his underground quarries outside Louisville is now a secure data center for companies fearing above-ground disasters. A restaurant space attached to Louisville's minor-league ballpark houses a brewpub and one of the city's most ambitious restaurants, both owned by Rechter.

Yet with all that, and a bout with prostate cancer thrown in, his involvement with the Cardinals has only grown. Sitting in the stands during an early-season game, Rechter ticks off his social activities for the previous week. "We went to an NCAA women's volleyball regional, then a basketball game, then another basketball game," he says. "We watched the football team play Connecticut on television, and now here we are at another basketball game. We go to softball games, ladies basketball, soccer games, field hockey games. Not all of them, but four or five a year." Some years, he has attended as many as 25 of the Cardinals' 28 or 29 regular-season men's basketball games, flying around the country—and then followed the NCAA tournament run.

Rechter doesn't consider that commitment extraordinary. Booster friends who offer similar are far busier than he is, he says, and to prove it, he calls Mitch McConnell, the second-ranking Republican in the U.S. Senate. McConnell has the same relationship with Louisville football that Rechter does with Louisville basketball. "To give you a sense of what my priorities are, I missed one game [last] season," McConnell says. "It was a Thursday night and we were in session. I missed another one two years ago, when I was in Iraq. Louisville football is my major extracurricular interest."

The idea of knowing what's happening inside the athletic department holds little currency for McConnell, who is an insider on matters of national and world affairs. Hobnobbing with a football coach is hardly compelling when you hobnob with world leaders. Yet McConnell, who produces a Louisville calendar each Christmas for his friends, is as hooked as any fan and as eager to learn the latest doings of his team as someone listening to sports talk radio.

He tells of being on the Senate floor for the impeachment of Bill Clinton. During a break, the senators repaired to the cloakroom to discuss the historical events that were transpiring. Not McConnell, who would later that year read a tribute to former Cardinals football coach Howard Schnellenberger into the Congressional Record. Looking for something to clear his mind, he picked up a phone and called then-football coach John L. Smith, who was out recruiting. "We were after a big recruit, and my first thought as we walked off the floor of the Senate was, did we get him?" McConnell says.

"I couldn't believe it," says Smith, now at Michigan State. "That's the level of his concern for his school and his football program. And I say 'his' because he has a feeling of ownership, in the best possible way. You just wish you had more like him." Louisville's failures and successes can affect McConnell's state of mind, as is the case with many rabid fans, and on this occasion it almost changed the course of history. As Smith recalls, Louisville didn't manage to land its prized recruit. Coincidentally or not, McConnell voted to convict.

Bruce Schoenfeld is a Cigar Aficionado contributing editor.