Hailing from Edmonton, Renato Pagnani is a music journalist who’s contributed to Pitchfork, the Edmonton Journal, Rolling Stone, and The FADER. In 2015, he was on the grand jury for the Polaris Music Prize, given to the best album in Canadian music, which Buffy Sainte-Marie won for Power in the Blood. I spoke with him to figure out why Drake — arguably Canada’s most popular artist and someone who’s singlehandedly responsible for making Toronto’s music globally relevant and important — just can’t win the top prize for Canadian music.

This year, Drake was nominated for his retail mixtape If You’re Reading This It’s Too Late. Previously, he made the Prize’s shortlist Nothing Was the Same in 2014 and Take Care in 2012. In hindsight, Take Care probably was the best effort in the pool that year (Feist won for Metals), but at the time, he was still starting from the bottom, earning credibility as a rapper and an artist. Still, Pagnani isn’t surprised by that particular loss, telling me 2012 “was the strongest shortlist in Polaris history.”

Before understanding why Drake fails, though, Pagnani explains to me why Sainte-Marie did deservingly win. “Sainte-Marie is kind of a legend amongst Canadian music. She’s 74, and she’s kind of been in the vein of a protest singer for her entire career.”

Her status in Canada is likely akin to that of American beatniks of the ’60s: We know them but don’t really listen to their music regularly.

“This is somebody who has won an Academy Award and a Golden Globe. She was a regular cast member on Sesame Street for five years back in the ’70s. I mean, she was even at one point essentially blacklisted and her music banned from the radio. Lyndon B. Johnson actually wrote letters to radio stations, praising them for not playing her music back in the day.”

With Sainte-Marie’s credentials firmly established, it’s worth considering what Drake has to do to climb the Polaris mountain. “I think there’s still some resistance to rap as a whole amongst the jury,” Pagnani says. “I don’t think it’s intentional, but it exists. I think any genre that’s not guitar-based goes into an award like this with an automatic disadvantage.” He says it just might not be received as immediately “‘Canadian’ as much as, you know, a throat singer from Nunavut,” referring to 2014 winner Tanya Tagaq.

But what about all that 6 shouting Drake does? Shouldn’t his global ambassador role (one he literally fills for the NBA’s Raptors) give him a boost as the country’s most important artist? That success comes internationally, though — not just in Toronto. That could affect his actual presence in Canada. “I think one of the big reasons Drake has found success outside of Canada is he’s kind of come up with a new sound. He and his producers have kind of spun it in a different direction and came up with what people refer to now as the ‘Toronto sound.’” The reality remains, he tells me, “Drake very much is equally influenced by Houston rap as he is Toronto rap.”

Ultimately, Pagnani says all Drake can do is put out good music. “I think a rap album has to be twice as good to even be considered to win the prize.…If You’re Reading This It’s Too Late has a bunch of moments. Its best moments are quite possibly the best moments in Canadian music this year, but I will admit that it doesn’t hang together as a capital-A Album in the traditional sense that his previous two did. It’s quite long. There are a few moments that he could have cut, but it was also released as kind of challenging the preconceived notions of what an album is.”

Pagnani thinks Drake’s best shot at the award may come once this current Drake wave ends and we appreciate his work in hindsight — getting “Scorsese’d,” as he calls it. Drake may be Canada’s most important artist, but his job is bigger than simply being a musician from the North. He makes his home nation relevant, which allows smaller acts to shine. His shortlist presence alone gives a boost to the Prize, giving winners Sainte-Marie and Tagaq, as well as the various nominees the limelight their work deserves.

Photos via Kevin Winter/Getty Images for Coachella