No one knows exactly what they talked about on the morning of Dec. 13, hundreds of feet above Fifth Avenue. “Multicultural issues,” if you believe Kanye West’s twitter account. “Life,” Donald Trump told a hoard of reporters as he escorted West out of his golden palace. “We discussed life.” Meanwhile Kanye stood by, subdued — the latest to kiss the ring of the gloating president-elect, his own dignity dimmed accordingly.

To many of West’s longtime fans, this would seem to be the ultimate in a long string of humiliations — outbursts of arrogance which have become harder to make excuses for as the once-brilliant rapper retreats into a self-absorbed world of luxury and Kardashians, showing serious signs of mental illness that have prompted several former associates to insist we should be concerned for his well-being.  

This latest episode is impossible to separate from that unraveling, considering the near incoherent onstage rant that preceded West’s forced weeks-long stay in a Los Angeles psychiatric hospital — the rant in which he derided Hillary Clinton, admitted he would have voted for Trump and declared “It’s a new world!” to a booing crowd before ending the concert only three songs in.

Taking all this into account, it’s disturbing but perhaps unsurprising that one of Kanye’s first actions after emerging from psychiatric care was to visit the fortress on Fifth Ave. Even on the surface, they would seem to have a distressing amount in common: they share a compulsion to surround themselves with luxury goods and beautiful women in lifelong quests to assert a gaudy sense of status; both have cultivated an increasingly hostile relationship with the press; both have become known for long, stream-of-consciousness rants that inevitably loop back to their own accomplishments; both have developed reputations for being “outspoken,” as their fans might call it. There is certainly a similarity in the way they both ramrod through norms of civility without second thought, no matter how misogynistic or crude they come off; insisting on their right to be themselves, however offensive or disconnected from reality.

That unfiltered “outspokenness,” and the assumed authenticity connected with it, would seem to be as much a part of Kanye’s brand as it is of Trump’s. The grandiose sense of self, too, is as central to Kanye’s “greatest artist of my generation” mystique as it is to Trump’s power-player shtick. These are men convinced they are great and capable of doing anything they want, breaking any boundary, despite the broad choruses of naysayers. From a career of playing the outsider — first as the kid with the backpack and the pink polo trying to break into early 2000s gangsta rap, and now as a musician trying to break into high fashion — Kanye probably saw a lot to admire in the way Trump withstood waves of awful press and countless gaffes, only to triumph over Washington’s political culture in the end. This isn’t just speculation — Kanye recently compared their struggles himself, bursting out, “Just look at the president. He wasn’t even in politics and he won!”

But there’s a limit to this game we’re playing — stacking up attributes in the middle of the Kanye West/Donald Trump Venn diagram. At a certain point, we do a disservice by equivocating these two public personalities — and this is where I believe Kanye’s fatal mistake lies as well. Kanye may see an ally in Trump, someone to crawl to when he feels at his lowest — but he’s playing into the authoritarian’s endless circus 0f self-gratification, trading his integrity for a hit of someone else’s ill-gotten success.

Whatever he was before, Trump is now a politician, among the most powerful in the world — a position he attained by inflaming racial anxiety against minority groups and smearing his opponents as weak establishment stooges. Trump’s gold-tipped, ultra-nationalist strongman image is one of brash, incredible power, and it has an immense gravitational pull for many people. As Slate’s Katy Waldman writes, “it may not be shocking that Kanye, whose visionary tirades about the potential of the artist have a fascist undertone, gravitates toward a bully like Trump.” And Kanye’s grandiose fantasies of power and control, gloriously realized on ornate, thunderous albums like My Beautiful Dark Twisted Fantasy or Watch the Throne, certainly fit into that mold — fascism’s worship of strength and human perfection at any cost. As Waldman writes,

“West and Trump’s dynamic — the artist and the strongman — evokes a traditional symbiosis between aestheticism and fascism. In the visually ravishing films of Leni Riefenstahl, the crisp goose-stepping of smartly uniformed troops, the propulsive fervor of futurism, we’ve seen politics married to the pursuit of the beautiful before.”

screen shot from Kanye West's video for "Power"

screen shot from Kanye West’s video for “Power”

In sucking up to Trump, isn’t Kanye acquiescing to lust for fame and power, the most base among his demons?  Has the pursuit of the image, that all-consuming black hole at the pinnacle of our society, finally claimed Kanye’s soul?

To be less dramatic, was the flash and charisma of Trump’s political takeover the last push Kanye needed to completely forget where he came from? He even got a Slim Shady hair-dye — don’t go Hitler Youth on us quite yet, Kanye!

There was a time when he truly embodied the underdog — just a kid from Chicago, fighting to be heard. There is real courage in the way Kanye has stood up for the downtrodden in the past, like when he took Bush to task for his handling of New Orleans black community during Katrina, or when he called for an end to homophobia in hip hop.

As a fellow fan told me the morning of the Trump Tower visit, “Kanye may have forgotten that he’s a black guy from Chicago, but I haven’t.”

“Oh god…what timeline are we on?” I remember someone saying when I mentioned the Kanye-Trump meeting. I laughed — but it was a hollow horselaugh, because the absurdity can only amuse for so long. Then I remember all those adolescent mornings and afternoons I spent immersing myself in Kanye’s songs — riding the bus to school with College Dropout in my earbuds, or lounging around my room letting Late Registration repeat over and over — and I grimace.

Like so many people of my generation, I grew up with Kanye West — he loomed large over the pop culture of the last decade, as much for his bursts of wild behavior as for his music. But the music! As a teenager it swelled to fill my entire universe. I saw Kanye as the pinnacle of hip-hop evolution, a master of samples who subjugated entire musical worlds to his will. You could hear it in the classical orchestras, the synth-pop, chamber pop, the warm soul-inflected soundscapes of his first albums. All that virtuosic mastery meant you could defend Kanye on musical grounds to every white adult who shook their head in disbelief. You call that music? Hell yes! It had personality. A personality, to be exact, which was always fresh and defiant, but also self-conscious, at times anxious and vulnerable. He was the perfect cipher for adolescent anxiety, because he spoke its language — constantly feeling victimized and still somehow overcoming it, whether in his struggle as an artist to make it out of obscurity, fighting for respect as a black man in America, or simply as someone who wanted to be their authentic self on the public stage without conforming to expectations of how a rapper should act. This was the Kanye people loved. This was the Kanye I loved — and still do, on some level.

In the gangsta/club rap wash of the 2000s, Kanye’s musical ambition and pursuit of authenticity didn’t just make him famous — it made him into something of a saint, and his disciples, of which I would eventually be one, gave him numerous passes for the arrogance that fame drew out of him. That arrogance would come to overshadow the music as the years flipped past, even as the music grew grander alongside his warping persona — despite racking up Grammys, he threw tantrums at award ceremonies, accused the president of racism (rightly), drank too much at the VMAs and stage-crashed America’s sweetheart…the list goes on.

First, his mother died. Then a string of public, failed relationships. Then the marriage to Kim Kardashian, the album-long rant against the fashion industry (Yeezus) that saw him flip a civil rights anthem into a hopelessly self-absorbed breakup song, the laughably deluded, off-the-rails interviews on Sway in the Morning and BBC 1, the “BILL COSBY INNOCENT” tweet…

The personality on display was increasingly tone-deaf, prone to fits of self-pity — the I’m-so-misunderstood platform that had once been compelling in its vulnerability was becoming a caricature of its former self. The rants and freak-outs, once just another facet of the artist’s colorful and ambitious personality, sounded increasingly like cries for help — cries which only became louder as he brawled with paparazzi and dropped hints that he’d been off-and-on antidepressants over the past few years.

And now, here we are. Kanye West, the man who once called the President out on live TV for racial insensitivity, standing beside Donald Trump like another one of his lapdogs. One rumor alleged the two discussed a role for Kanye in the new administration — whatever bone Trump throws him will have come at a high price.