If a rapper spits long enough to serve up hits during their old-head phase, they’ve really made it. If they last beyond it and somehow remain central to every GOAT conversation, then they’re probably Jay-Z. There’s only one of them. But in June 2009, with the release of “D.O.A. (Death of Auto-Tune),” the first single from Jay’s 11th album, The Blueprint 3, Hov took aim at the chest plate of youth culture. A decade later, it’s clear now that “D.O.A.” kicked off a new era of Jay-Z, a time when the erosion of his influence on a new generation began to show. While acts like Kid Cudi and Lil Wayne ushered in the sadboy style that would define rap’s coming decade, Jay was remarkably defensive. “D.O.A.” was a middle-aged middle finger to the modulation the youths were fiddling around with. A tee shot at T-Pain. But it also showed the power and the necessity of Corporate-Artsy Hov. By that point in 2009, rap hardly paid Jay’s bills anymore and, perhaps even more importantly, the genre and its practitioners were beginning to shape-shift. Rap had become as vulnerable as rock ’n’ roll in the ’80s, when facile gimmickry and tepid musical trends made sonic space for rap’s transition into the dominant culture. Jay saw through it. Or so he thought.

“D.O.A.” holds the key to Jay-Z’s future—soon he would be a self-styled czar, gatekeeper, rap daddy, and marketing consultant while demarcating himself from the corroded voices infesting his territory. As a mentee of Biggie and mentor to Beanie Sigel and Memphis Bleek, Jay was known for his elder-brother tendencies and sage wisdom. Hov has given several explanations for taking aim on “D.O.A.,” each rationalized using that mentorship as a lens. First was Kanye West. The devil in the pink polo “actually sparked the idea,” Jay-Z told Billboard. “When he heard the beat he said, ‘Man, this is just so hard! This has to be against everything—no Auto-Tune, none of that type of stuff!’ He didn’t know what I was going to do or where I was going to take it, but it was actually his fault.”

Prior to making the single with producer No I.D., Jay had already prepared a song with Ye featuring Auto-Tune—but once “D.O.A.” was mixed, they decided to trash it altogether. Therein lies Jay’s more proprietary reason behind “D.O.A.”: He sees it as his duty to filter and push things forward.

“In hip-hop, our job is once a trend becomes a gimmick, to get rid of it. We’ve done that since the beginning of time,” he quipped during a 2009 appearance on Big Boy’s Neighborhood. Not only is this reductive, it’s anti-capitalist in a way that betrays Hov’s guiding principles: exhaust the value of the hot shit until that value isn’t worth the investment—then sell, sell, sell. Auto-Tune, as a tool, wasn’t exhausted at this moment. It wasn’t even peaking. Jay started Roc-a-Fella Records with Dame Dash and Kareem “Biggs” Burke in ’96 only to sell half of it to Def Jam in ’97 for approximately $1.5 million. Seven years later, Def Jam bought the whole thing for $10 million and Jay became the CEO. He played the game similarly for the music-streaming app Tidal, which represented a conglomerate of artists like West and Nicki Minaj pooling resources together for the benefit of higher profits per stream. He sold a third of it to Sprint in 2017 for $200 million. He bought a small stake in the Nets during an ownership-transition period when familiar faces like Kevin Garnett and Paul Pierce could make the team not just more profitable but more relevant to Brooklyn and the culture at large. He moved the team to his home borough, sold his stake, earned 135 percent of his original investment, and came out the other side clean, even as the vision for the team fell into purgatory. Whether or not one considered Bing a trend at the time, Jay seized the chance to partner with Microsoft during the release of his book, Decoded, for a marketing campaign for the fledgling search engine just a year after BP3 hit the market. He was, finally, a business, man.

This ain’t just rap, it’s the culture writ large, and every good businessman knows a bankable trend when he hears it. So when Jay calls for anti-Auto-Tune propaganda and the “death of the ringtone,” it just sounds strange. Perhaps the issue here isn’t one of profitability but personality. Jay couldn’t find a way to incorporate Auto-Tune into his music. Shuffle through pretty much any Jay-Z record before “D.O.A.,” you’ll likely notice that there is absolutely no modulation. The man hardly layers his vocals or produces ad-libs, instead opting for an organic Brooklyn lilt that feels untouched. Even on “D.O.A.,” which was constructed from squelching horns, quips inspired by Steam’s “Na Na Hey Hey Kiss Him Goodbye,” and Yeezy’s “Big Brother” (which I’m convinced is some sort of inside joke), Jay sounds pristine even with that mucusy “argh” perioding each line. The distance between Jay and the rest of the rap world would only grow from there; he plunged into dreamily aspirant arthouse rap that rubbed a lot of his longtime listeners as uptight and bougie.

“D.O.A.” signaled Jay’s sharp turn toward themes steeped in leisure. Obnoxious wealth—its acquisition and promotion—would define his output until 2017’s 4:44. BP3 was an intermediary period in which his coke-push flow collided with the reality of Jay’s present, a present that was in flux. Coming on the heels of the American Gangster soundtrack that allowed him to forge spiritual kinship with Frank Lucas, Jay faced the conundrum of the future by claiming his unmovable stature within it, but refusing to grant it any definitive character. It’s why tracks like “What We Talkin’ About”—where Jay is sick and tired of the same small-minded dudes talmbout the same ol’ rappity rap shit (“The conversation has changed let’s yap about that / I don’t run rap no more I run the map”)—seem a little … off. It represents a concession. Y’all can have that rap shit, we off that.

He says as much on “Off That,” where rap’s entrenched symbols that he once so gloriously traded in mean so very little to him, “The only time I deal in past tense / Cause I’m past rims and I’m past tints / If you driving it I drove it / You got it ’cause I sold it / You copped it and I bought it back.” But if the past tense doesn’t define him, his future was just as undefinable. Hov is “Off That” and “On to the Next One.” But where he was going was still up in the air.

And where he ended up was Family Fun Day at The Met. Where he ended up was erecting modern art installations with Marina Abramovic and performing a song dedicated to Picasso’s artwork vibing out with little white boys who rock and sway on the 1 and the 3 for six solid hours. All for the sake of … I’m not exactly sure. Hip-hop was already being taken seriously as an artistic endeavor by that time, but 2013’s Magna Carta Holy Grail made Jay seem ungraspable, the symbols of indulgence so far from the hands of those who found promise in the darkness of his earlier work and levity in the bling era of his sound. The Blueprint 3 provided an opening for Jay-Z to pivot, and he did. Magna Carta indulged in such a way that even the burgeoning black middle-class youth had to press pause. It featured more distancing. On “Tom Ford,” he’s at the grown folks’ table patronizing the kids who pop Molly for kicks. In another life, at another time, Hov might be the one to press the pills in their hands on the street corners. But Jay was also carving out a lane for aging rappers that had never really existed before. And that came with scrapes and misses.

Aging in rap is hard because no one really retires. In fact, the act of retiring as a rapper and almost immediately coming back is an eye-rolling trope that Jay-Z helped make concrete in the mid-’00s. Everybody comes back. Which, in a vacuum, would be totally fine if rap wasn’t so obsessed with competition and conquest. And, if we’re being honest, if the faces of hip-hop were a touch paler, retiring only to step back into the booth wouldn’t be read as the annoying, fresh money-grab it is. The Rolling Stones are still touring in 2019 because (old) people are willing to watch them in full AARP mode.

But these days, aging in rap looks and sounds painful, as artists like Kanye West, Nicki Minaj, Drake, and J. Cole tether themselves to vile artists like XXXTentacion, Tekashi69, and Kodak Black for clout. In sports, there’s usually a moment in a star’s career—Kobe and the Achilles, Bird’s back, or the Dream’s Toronto stint—when it’s clear to everyone that the end is near. For rappers, there’s always potential for work that the culture considers meaningful. Neither BP3 (a tragedy of high expectations pre-baked into the title) nor Magna Carta felt pressing or present enough for outsiders to defend from detractors. For Mr. Carter, it took eight years and a betrayal of his superstar wife to paint what felt like a genuine picture of his life. No one’s interested in how much he paid for the Basquiat. We want to know about Jay’s soul as he reaches a billion and the world underneath him crumbles.

Say what you will about The Blueprint 3 and the years and records thereafter, Hov is still teaching rappers what it takes to create something meaningful: losses. Any investor takes what they consider to be a worthwhile risk. But what may seem like a risk to one—“D.O.A.”—is just a sunk cost to the outside world. Both Auto-Tune and Jay-Z are still with us. And while both have fielded attacks from within and without, each has been elemental to some of the genre’s most vital work. Auto-Tune is not a gimmick—it’s a tool. One that young people are still gauging the limitations of, even today. The duty of the artist is to use any and every tool at their disposal. To cause them to move. But for Jay, his primary tool will always be his own voice. Even when he doesn’t have all that much to say.