On Friday, Mac Miller died of an apparent overdose in his California home. This increasingly common story doesn’t become any less tragic every time it’s told, whether the victim is a loved one, a celebrity, or a stranger.

In the wake of his death, fans will likely stress the fact that Mac Miller, or Malcolm James McCormick, was so young—only 26 years old. They’ll talk about his talent, and his promise, and the fact that he meant so much to so many people. Miller struggled with mental health and substance abuse and bravely put those conversations into his music, out of the shadows, forging important connections with listeners in the process. He was not afraid to make an impact, or to take a stand where it counted.

In 2011, Mac Miller released the single “Donald Trump,” his first hit to chart on the Billboard Hot 100. The track and accompanying music video are an ode to what Trump used to symbolize, back when his name was just a shorthand for flashy living and extreme excess. Miller rapped about his own imminent come-up, saying, “Hopefully, I’ll be at the top soon / For now, I'm at my house on the couch, watching cartoons.”

“Take over the world when I’m on my Donald Trump shit / Look at all this money, ain’t that some shit” the track repeated, with the Trumpian promise that “We gonna take over the world while these haters gettin’ mad.” Of course, the Pittsburgh native wasn’t making a political statement at the time. And Trump, then a real estate mogul and reality TV personality, made a video in 2011 praising the single. Gesticulating wildly, Trump informed his YouTube followers that people had been calling him about the “Mac Miller rap song,” and told them that “it just hit over 20 million.” Trump went on to crown Mac Miller the “new Eminem,” despite having difficulty parsing out the actual lyrics on the track. “The Donald Trump song just hit over 20 million, that’s not so bad,” he concluded. “I’m very proud of that.”

But in February 2012, Trump took to Twitter to address Miller directly, complaining that the song named after him “has had over 40 million hits. Maybe he should pay me something.” The tweets escalated, as they tend to do. By March 2015, Trump had tweeted about Miller nearly 50 times.

Trump appeared to have been particularly enraged by a 2013 Complex interview in which Miller expressed profound regret over the track, saying, “I think he’s a dick…when he started running for president I was like ah fuck, this is horrible, I have a fucking song with this dude’s name and now he’s just being such a fucking douchebag.” Choice Trump responses included: “Little @MacMiller, I’m now going to teach you a big boy lesson about lawsuits and finance. You ungrateful dog!” and “Little Mac Miller’s next album may bomb. He can’t use my name again for sales.”

That same year, the future president of the United States tweeted, “It was just announced that @MacMiller’s song ‘DonaldTrump’ went platinum—tell Mac Miller to kiss my ass!” The Apprentice star was not appeased by the plaque that Mac Miller reportedly sent him when the track went platinum, calling it a “crummy gift.”

But in 2015, The Hill revealed that the Republican presidential hopeful still took pride in the song, and “ended an interview with The Hill by playing rapper Mac Miller’s ‘Donald Trump’ song.”

“The billionaire business mogul and reality TV personality had an aide in his Trump Tower office lobby load the song onto a computer,” the article continued. “‘Do you have that Mac Miller thing?’ he called to his staffer, exiting his corner office on the 26th floor. ‘I want to see how many hits.’ The YouTube video for the song has more than 99 million views. ‘Almost a hundred million hits,’ he said, nodding his head.” Later, Trump added, “By the way, great song.”

In December 2015, Mac Miller tweeted, “Just please don’t elect this motherf**ker man.” In the same thread, he added, “Also white people, reverse racism isn't real. Racism describes a system built to keep a race or ethnicity away from success and evolution,” and asked, “Dear White People who listen to rap music... What have you done for the #BlackLivesMatter movement”? He concluded, “Just don't forget about the ridiculously large amount of humans who are down to have Donald Trump be present. There is work to do.”

“I hope it doesn’t lead to people thinking I’m supporting his run,” Miller told Vanity Fair about his Trump-inspired track in early 2016. “I made the song in 2011. It was just somebody who symbolized financial success to everybody at that time.”

“He’s entertaining but not somebody I want to be the face of what the United States of America represents,” the rapper continued. “Plus he doesn’t fuck with Obama… can’t fuck with somebody who doesn’t fuck with Obama.”

In case he had not yet made himself clear, Miller graced The Nightly Show in March 2016 and shared more thoughts on the reality TV candidate. “I only have one thing to say: I fucking hate you, Donald Trump,” he began.

“Make America great again? I think you want to make America white again,” he continued. “I come here today as a white man with the hope that maybe you’ll listen to me. In other words, let me ‘white-splain’ this to you, you racist son of a bitch.”

He called Trump an “egomaniacal, attention-thirsty, psychopathic, power-hungry, delusional waste of skin and bones” who would “do, say, or allow anything if it means you’ll just get one more minute in the limelight.” Were he to be elected, Miller insisted, “I’m not going anywhere. I’m gonna be here every day telling the world how much I hate you, how much of a clown you are and how we as a nation are better than you will ever be as a racist fuck-wad of a human, because I love America, and I’m never giving it up to a troll like you, you bitch!”

Despite Mac Miller’s frequent and fervent Trump bashing, Trump remained attached to his namesake track. According to released transcripts related to the infamous June 2016 Trump Tower meeting between Donald Trump Jr., Jared Kushner, Paul Manafort, and Russian lawyer Natalia Veselnitskaya, Trump enjoys listening to “Donald Trump” in his free time. British music publicist Rob Goldstone recalled in the transcripts the last time he saw Trump in person: “We went and had about 10 minutes with Mr. Trump... Mr. Trump at the time was listening to very loud rap music when we walked in, because he knew I was in music, said, look, I’ve been presented with a platinum disk for a song called, ‘Donald Trump,’ to which I—that’s how I remember this incident. I cautioned him that he should perhaps look at the words to the song before he enjoyed it so much.”

When Trump was elected president, “Donald Trump” charted again, reentering the iTunes Top 30. But Mac Miller was able to embrace the song’s popularity while still roasting its subject, telling Rolling Stone, “I still play it. It’s a banger. It goes hard at shows. We change it up a little bit, like we say ‘Fuck Donald Trump’ at the beginning. It has never been an ode to him.”