Times were much simpler in May of 2009. Barack Obama was the newly inaugurated President of the United States, Michael Jackson was alive, Instagram didn’t exist, LeBron James was the MVP of the NBA, and Kobe Bryant was just weeks away from his fourth NBA title and first without Shaquille O’Neal by his side.

On the Billboard charts, Eminem, JAY-Z and 50 Cent had the biggest rap albums of the year, and while that felt like a decade-long stasis, one Billboard supernova had quietly emerged: Drake. On May 23, 2009, Drake modestly began the most dominant chart run in music history, as the So Far Gone standout “Best I Ever Had” debuted on the Hot 100 songs chart at No. 92. From that point on, at least one Drake record would remain on the Hot 100 chart for 431 weeks, a record for all genres and two years longer than his closest competitor, his mentor Lil Wayne.

The run is a testament to Drake’s ability to craft both culturally-shifting moments almost every time he decides to release a record and his malleability during that eight-year run. In that time, he’s emerged as one of pop’s biggest acts, and the rare artist that transcends rap stardom and reaches a whole other level of fame. The fact that it took until 2015 to actually top the Hot 100 with “One Dance” is evidence of both his staying power and the fact that even while constantly churning out hits, he somehow managed to remain fresh and gain new listeners throughout his run.

Now, that streak has ended, but Drake has begun another run. He currently sits atop the Hot 100 with “Nice For What” after becoming one of only 13 acts, ever, to knock themselves from the No. 1 spot with a new No. 1 song. But despite a run of sustained popularity and unprecedented chart success unlike anything rap has ever seen, Drake finally appears to have a few chinks in his armor. His last two albums, 2016’s Views and 2017’s More Life received lukewarm critical reviews. And after Views sold 1 million copies in its first week, topping all albums in 2016, More Life did half that in its first week on the shelves.

Perhaps more damaging was Kendrick Lamar’s run of Drake-like chart success and record sales. His 2017 album DAMN. outsold More Life in its first week, spawned five Top 20 singles and officially gave Kendrick—long considered Drake’s closest competition—the commercial edge over him for the first time in his career. Kendrick had always been the critical darling of the two, but now boasted the numbers and accolades worthy of comparison, making success a moot point in raging debates over who was the best.

Now, Drake has suffered the most punishing blow to his previously unassailable career, as Pusha T took aim at him with the scathing diss track “Story of Adidon” after years of jostling and jabbing between the two. Pusha T managed to beat Drake at his own game, hurling insults he couldn’t duck, and then mastering the social media machine to add that extra oomph to those punches. The diss lingered, and shifted the tides of the battle, even after Drake seemed to successfully get off the first real shot of the war-of-words with the equally-thrilling “Duppy Freestyle.”

For a certain sect of hip-hop fans, Push would always get the popular vote, as he represented something that Drake could never be. Push represented a sort of authenticity and traditional archetype of what a rap star should be that Drake could never capture. Drake was an actor, and may still be one in a sense, but Pusha T is real rap and, for many, someone of Drake’s ilk simply cannot beat that.

But Pusha’s diss came with more bite and captivated the public in a way that no Drake attacker ever had. In one fell swoop, Push had earned the support of the general public against a guy whose entire career was built on earning the support of the general public.

So, Drake also lost in the eyes of the more mainstream fan, as well. While he may have emerged from the Meek Mill tussle relatively unscathed despite threatening reveals like reference tracks and tales of unwanted golden showers, he did not get off so easily against Pusha. In his assault against Drake, Push managed to reveal Drake has a secret lovechild, expose an embarrassing blackface photoshoot from years ago, and insult his parents, his sick friend and his insecurities, all for Drake to issue a statement but musically remain silent afterwards.

Now that Drake benefactor J. Prince and frenemy Kanye West have essentially called the beef off, Drake has been handed his nice, shiny L and cast aside while Pusha does his victory lap. While J. Prince may have been trying to do Drake a favor, cutting the cord before the beef got too ugly or too personal, he really did him a disservice, making the rapper long suspected of being “soft” appear more soft than he ever has as he bows to the feet of not only his most respected benefactor, but his opponent as well.

The loss is an embarrassment that Drake has yet to see thus far in his career, and the kind of public humiliation he’d been able to shake off for the past decade. Now, he finds himself on the defensive for the first time ever, and needing to deliver an album so good it shines the blemishes and shaves off the rough edges and scrapes that Pusha left on his normally spotless veneer.

His forthcoming album Scorpion could be that, if he’s spent the last year truly crafting something special. But if the latest single “I’m Upset” is any sort of preview, it has only served to lower expectations. That song, combined with previous leaks, doesn’t seem to hint at an overlying theme for the album. If anything, those songs only show that Drake is going to release yet another, disjointed effort meant to cover as many bases as possible for commercial purposes, not to deliver artistically.

For the first time in his elongated run, Drake stands perilously close to that precipitous edge of the cliff that all artists eventually run up against: the difference between relevance and irrelevance, the difference between platinum and flop, and the difference between the top of the mountain and the devastating avalanche-aided tumble to the bottom.

It’s easy to say Drake is simply too massive to ever truly disappear or fall from grace, and that may be true, but every run has come to an end in some way, shape or fashion. Ominously, Drake may have sealed his own fate and projected his own demise back in summer of 2016 when he said on “4PM In Calabasas”: I got a lot to lose, ’cause in every situation I’m the bigger artist, always gotta play it smarter. He was right; he is the bigger artist, and now we’re going to find out just how much he had to lose, or if he played it smart by bowing out just in time.

Scary hours, indeed.

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