T. Boone Pickens died on September 11, 2019 at the age of 91. Pickens died rich — like, really, really rich, thanks in large part to a lucrative career in the oil and gas industry and a lifelong thing for big mergers and acquisitions. His reputation as a corporate raider peaked in the 1980s, but Pickens was raking in piles of cash well into his eighth decade, making $2.7 billion in 2007 alone.

Pickens would have died a billionaire if it hadn’t been for two things. The first is explicable: Volatility in the oil markets cost his companies some serious cash. The second is harder to explain. For some reason, Pickens gave Oklahoma State University at least $652 million over the course of his lifetime, including a record $165 million one-time donation to the Oklahoma State Athletic Department in 2005.

When Pickens died, college football lost its most prominent and public megabooster.

The megabooster is not the average donor. They’re not even your average large donor, really. Megaboosters give to programs often and in big chunks from bigger bankrolls. Their check-writing allows them access to everything in a program, sway over almost everyone in and around it, and the privilege of putting their name on whatever they want. They might turn a team’s fortunes around singlehandedly. They might hurt the program and help drive it into a decades-long downturn. It could go either way, but in the end if they’re writing the checks, they will have their say.

T. Boone Pickens is the case study in outsized influence by a megabooster, both because of his unique largesse, and also because of how publicly he ruled as the Cowboys’ de facto team owner. Pickens didn’t expect a salary and shares for his investments, sure — but he didn’t write a letter each year to Oklahoma State fans outlining his expectations for the school’s teams for nothing, either.

As a megabooster, Pickens used his power in a lot of little ways — and in a few big ones, too.

For instance: In 2004, Pickens offered to pay for new practice fields for the football team. When Les Miles failed to answer Pickens’ questions about whether the coach wanted artificial turf or real grass for those fields, Pickens’ relationship with Miles began to sour. The Cowboys’ megabooster left the blowout loss to Ohio State in the 2006 Alamo Bowl at halftime, but was saved the trouble of lobbying for Miles’ firing when LSU hired him away that year.

When it came time to hire Miles’ replacement, Pickens thought Oklahoma State assistant Mike Gundy would be a great candidate for the open head coaching job. Athletic director Mike Holder listened. T. Boone had to feel pretty confident about getting Holder’s ear; the former Oklahoma State golf coach was Pickens’ “hand-picked” choice for the job. A megabooster doesn’t just get to hire and fire coaches. They get to hire and fire the people who hire and fire the coaches, and pick which hands get to hold the checks they pay to the program for prime seating in the stadium, or sometimes even for the stadium itself.

That stadium — the one literally called Boone Pickens Stadium — is another way a megabooster can push weight. Money begets money in donations and fundraising. It’s not that Pickens’ $165 million gift paid for stadium renovations by itself. It instead anchored a larger overall fundraising push for the stadium, effectively bought the naming rights to what was then called Lewis Field, and spurred other rich donors into coughing up cash for the cause.

That level of giving has its own side benefits (hello, stadium-adjacent parking), but none of those explain why someone who excels at making money would give huge sums of cash to a college athletics program.

For starters, there is no possible direct financial return on an investment in an athletic department — the money buys zero actual shares in anything. It returns no up-front profits, though perhaps it yields some side deals. College athletics makes a terrible case for charitable giving, especially when there are actual charities and non-profits to support that don’t have the problem of harboring suspiciously profitable, off-the-books businesses like college football and college basketball.

So what is it, then, for megaboosters?

Why would anyone throw money into this hole? One that, despite being festive and filled with non-monetary perks, is still very much a hole from which money will never return?

Affection can explain a little of that generosity. In Pickens’ case, the future young tycoon lost a basketball scholarship to Texas A&M after only a year in College Station. The legend is that the scholarship cost $25 a month, and ultimately might have cost the Aggies somewhere in the vicinity of $650 million in lifetime giving after Pickens transferred to Oklahoma A&M — the school that would become Oklahoma State University.

Affection for the old school can’t explain Pickens’ driving need to push expectations at Oklahoma State. Jerry Jones, of all people, might have provided an actual insight here as to what fuels the rest, both for Pickens or for any other megabooster happily and seemingly irrationally writing checks to pay for things they can never really own.

Jones — himself a big donor to University of Arkansas athletics, and a good friend of Pickens’ — told ESPN in PIckens’ obituary that the man simply couldn’t stop competing. He was to the end pathologically ambitious in almost everything he did. Pickens shot on the first day of dove hunting season for 76 straight years, played for real money in golf, publicly criticized his otherwise wildly successful football coach Mike Gundy for not beating Oklahoma enough, and once got stuck inside SMU’s stadium at night in 2003 when he wanted to take some undercover notes on the competition’s stadium.

For wealthy sharks that don’t sleep, like Pickens or other megaboosters, writing checks to become shadow ownership opens up a lane to channel all their cutthroat instincts into something both unique and uniquely suited for them. Yes, giving to an athletic department is technically charitable giving. It can also be a down payment on ownership of a franchise, one where the lack of potential profits is balanced out by all the things college sports can be that professional sports can’t.

That list of things isn’t insubstantial. Professional sports might be more outwardly profitable, but professional sports owners face regulations, the inconvenience of profit sharing, the demands of labor, and competitive market pressures from every side. Even worse, limitations on their own power come in the form of the worst nuisance imaginable: other rich guys trying to run sports franchises. Even under pure capitalism, they are chained down by their wealth, the markets, and the hell of other people’s influence.

College boosters in comparison don’t even have to worry about profits. Freer than even very free pro sports owners, the megabooster with control over a program can do mostly what they want, all without worrying about ever paying the labor and only rarely having any limitations placed on their influence.

There is even a perverse flex built into college athletics boosterdom. While a pro sports owner has so much money they can display it by acquiring a professional sports franchise, a college booster has so much disposable income that they can acquire a share of an amateur sports franchise without even sweating that none of that money will ever see a penny of return.

They move mostly without restrictions. Look at the Haslams’ influence over the Tennessee football program over the past two decades, and tell me they’ve listened to anyone about anything. Consider Louisville athletics, freshly divorced from the clutches of megabooster John Schnatter only after multiple public embarrassments and a documented instance of Schnatter using a racial slur. No one asked for this — or for the burnouts Schnatter did in his Camaro in the stadium during halftime — but they got it anyway because Papa John’s garlic butter money was endless and flowed on schedule into Louisville athletics.

Nothing is for sale, but almost anything can be bought in college athletics with the right sum.

It’s not the same as everything else in America, though. It’s worse, because with actual ownership comes a bare minimum of responsibility and visibility. The megabooster you know, the colorful, vocal ones? They aren’t even the really scary ones. The quiet ones, the ones like Alabama’s cadre of silent influencers who stock the Boards of Trustees with their representatives and pay off Nick Saban’s house as a contract perk? They’re the terrifying ones, efficient, dedicated, and above all bent on keeping how things work as quiet and off the books as possible in order to win and continue winning.

Pickens at least had some emotional attachment to Oklahoma State to temper that need to exert power. Even then, his unrelenting need to use athletics as yet another game to win never faded. This year, the final edition of his letter to the Oklahoma State fanbase was a warm, affectionate note with a good streak of gallows humor. (“I love to tell the story – over and over – about the geologist who fell off a 10-story building and, whizzing past the fifth floor, hollered, ‘I’m not dead yet.’”) It was wistful, even. It talked about memory, what he cherished most, and how he believed his $652 million in donations to Oklahoma State had already paid off its initial investment for him.

And in case someone might think he’d gone soft at the age of 91, Pickens closed with these two sentences.

I want championships across the board. I hope you understand why, and I hope we get them while I can still savor the victories.

The Oklahoma State megabooster also stated that his goals for Oklahoma State were to win the conference again, and then to make the final four of the College Football Playoff. Pickens, in a last note confronting his own mortality, reminded everyone of the exact total he’d paid not to be associated with a loser of a football team or a school.

Even among his ruthless peers, T. Boone Pickens was an exceptional case. At the age of 91, he considered eternity in the distance, and then openly wondered if he might bookend it with a Big 12 championship and a Playoff slot.