I don’t know much about money, at least not as a theoretical construct. As a man who has spent the majority of his adult life as either a student or a freelance writer, I have not really had the chance to learn about such things. Investment opportunities don’t really appeal to you when you have no money to invest after all. Plus, my anxiety would make any such scenario an absolute nightmare for both me and everyone who comes in contact with me on a regular basis. Instead of making prudent decisions about my money’s long term viability, I buy immediately depreciable items such as books, old soul 45’s and Nintendo Switch games. All of which is to say that I’m not quite clear what exactly it is Spencer Dinwiddie is trying to do with his contract extension by converting it into a “secured digital investment,” but it is nevertheless an interesting decision that says a lot about how players see money, themselves, and their future prospects.

Shams Charania’s report for The Athletic about Dinwiddie’s decision to convert his contract is full of strange phrasings that in their quest to provide specificity with tons of technical language only obfuscate. There are a number of phrases — “digital currency world” and “digital investment vehicle” among others — where I know what the individual words mean but struggle to make sense of what they mean as a unit. But here’s what Dinwiddie is hoping to do in layman’s terms, which not so coincidentally are all I can provide in this matter. Instead of just receiving his contract as he normally would, Dinwiddie is hoping to receive a larger payment upfront which he can then invest elsewhere though where he hopes to invest has not been revealed. The strangeness of this decision lies not only in its novelty, but in its seemingly contradictory nature as he is seeking more money now but it is being described as an idea with long term benefits and the hopes of future returns. I guess that’s technically how all investments work, but it does raise the question of what investments Dinwiddie is hoping to make and why over $10 million annually is not enough to make them.

NBA players, more and more in this digital landscape where creating one’s own platform is easier than ever before, are seeing and establishing themselves as individual brands. Dinwiddie’s decision to take greater control of his financial life, in a way that is unprecedented for an NBA player, is yet another example of this. Even though branding may not be the primary reason for him doing this, it helps set him apart and enhances his notoriety among a set of people who may not be otherwise compelled to pay much attention to the Brooklyn Nets’ sixth man.

This also speaks to a wider interest NBA players are taking in the world of finance and technology. When Andre Iguodala and Kevin Durant signed with the Golden State Warriors in free agency, both were drawn to the on-court prospect of playing with Stephen Curry and Klay Thompson, but they were also lured to the Bay Area in no small part due to its being the centerpiece of the tech world. According to ESPN, in the last few years Durant has invested anywhere “from a $250,000 to a $1 million in roughly 30 companies through a network of venture capitalists,” with stakes in projects ranging from digital currency platforms to pizza chains, apps to drink companies, in addition to LimeBike, and Postmates, among others. Meanwhile, his former Warriors teammate Iguodala established the Players Technology Summit in order to bring together the nominally disparate spheres of sports, investing, and technology. While Iguodala and Durant are two of the most prominent players to dive into this world, they are far from alone and Dinwiddie, by attempting to gain money to invest while also showcasing a pronounced interest in cryptocurrency, is now joining their number in his own idiosyncratic way.

Dinwiddie is of a generation young enough to know about the pitfalls of previous stars who ran through all their money quickly, heedless of their inherently limited careers. They’ve seen the cautionary tales — the Antoine Walkers, the Latrell Sprewells whose earnings vanished quickly due to misguided investments and excessive spending. What’s not clear is if Dinwiddie, in this particular case is working to avoid similar pitfalls or merely making the same mistakes in a new way. What is also unclear is whether or not there is any market for investors to buy bonds from an NBA player. I mean, if you’re going to buy a bond, it does seems a bit cooler to buy one from Spencer Dinwiddie than from a starched shirt wearing employee at your local Wells Fargo branch, but then arises the question of whether it’s actually prudent or just a novelty. After all, other athletes such as Arian Foster and Frank Thomas have tried something similar in the past with limited success.

On the court, players still look up to their peers and previous generations of stars, hoping to emulate their skills and establish their own legacies, but off the court, players are looking more and more to billionaire investors in the hopes of someday coming closer to joining their rarified group. Perhaps it’s just that they’ve noticed how fickle their careers can be and are eager to form a financial portfolio that is more stable and not inherently limited by age and the whims of general managers. Perhaps they’ve noticed the power imbalance between themselves and the billionaire owners who sign their checks or perhaps it’s nothing more than them taking the words of Justin Timberlake in The Social Network to heart, no longer seeing a million dollars as that cool or aspirational. It’s impossible to tell at this point whether players such as Dinwiddie, Durant, and Iguodala are establishing a new way of handling money that will become a more widespread trend, or if investing in tech is just the late 2010s version of starting a record label, a misguided indulgence that will pass and become a cautionary tale for future generations of NBA stars.