One of the most fascinating—and tragic—beefs in the history of hip hop is the complicated, sometimes heartbreaking, fallout between Kanye West and Big Sean. What started as a mentorship and collaboration between two of rap’s most influential figures slowly evolved into a public feud that highlighted the darker side of the industry: betrayal, miscommunication, and the struggle for power. At the heart of the beef, though, is something that is more common than we often realize—feelings of being hurt by someone you once considered close.

Kanye West, one of the most influential figures in rap history, was a guiding force for many up-and-coming artists in the 2010s, Big Sean included. Signed to Kanye’s Good Music label, Big Sean’s career flourished under Kanye’s mentorship. But, as we’ll see, the same man who gave Big Sean his big break would later become the source of his deepest frustrations.

The Rise of Big Sean

Big Sean was signed to Kanye West’s Good Music label in 2007, at a time when Kanye was already one of the biggest stars in hip hop. For Big Sean, who had been grinding to make a name for himself in the industry, this was a dream come true. Kanye’s co-sign was everything, and Big Sean was ready to pay his dues. Over the years, Big Sean contributed to Kanye’s projects, worked with the label’s artists, and eventually built his own reputation in the game.

Kanye was known for his erratic, larger-than-life persona, but to those who worked with him closely, it wasn’t all genius and glamour. Big Sean, like many others in Kanye’s orbit, quickly learned that Kanye could be unpredictable, demanding, and sometimes impossible to work with. Yet, as a rising artist with much to prove, Big Sean remained loyal, always putting Kanye’s needs first, even if it meant sacrificing his own comfort.

The Turning Point: “Blessings” and the Studio Drama

The tensions between Kanye and Big Sean came to a head during the creation of Big Sean’s 2015 album Dark Sky Paradise. One of the standout tracks, “Blessings,” was a collaboration between Big Sean, Kanye West, and Drake. Things seemed to be going smoothly—until Kanye decided he wanted to get involved in the final stages of the song. Big Sean had already locked in Drake for the song, and the track was nearing its completion. But when Kanye heard it, he loved it so much that he wanted to add his verse—except there was one problem: the album was scheduled to release the next day.

Big Sean, ever the loyal artist, agreed to help Kanye record his verse at the last minute. At this point, Kanye was notoriously unpredictable, so Big Sean scrambled to make sure everything came together in time. He contacted Kanye’s engineers and confirmed they’d get the verse ready for release. But when the deadline approached, Kanye’s verse was nowhere to be found. Big Sean reached out to Kanye, only to hear vague excuses. This wasn’t unusual for Kanye, who was known for his last-minute creative bursts, but it left Big Sean in an incredibly tough spot. He had promised Drake that Kanye would be on the track, and he had a deadline to meet.

Eventually, Big Sean flew out to where Kanye was working to finish the verse, but when the time came to drop the track, Kanye still hadn’t delivered. The tension was building, but Big Sean felt that he had no choice but to press on and release the song without Kanye’s contribution. And this is where things really started to spiral.

The Fallout: Public Disrespect and Accusations

After Big Sean released Dark Sky Paradise and “Blessings” without Kanye’s verse, the relationship began to sour. Kanye, who was used to being the center of attention, was offended that Big Sean had gone ahead with the song without him. Despite Big Sean’s best efforts to explain, Kanye didn’t take kindly to being left out of the project, and he began to act out. Kanye’s jealousy and sense of betrayal began to surface in public.

Kanye didn’t just leave things behind closed doors. In an infamous interview during his 2020 presidential campaign, Kanye claimed that signing Big Sean was “the worst thing I ever did.” The comment shocked fans and industry insiders alike. Big Sean, who had always respected Kanye and credited him with launching his career, was blindsided. Kanye had publicly dismissed him as a failure, and it stung. To Kanye, Big Sean had betrayed him by not supporting his presidential run, but for Big Sean, it felt like an unjust attack on everything they had built together.

Big Sean, hurt and confused by Kanye’s words, responded by sharing the story of their falling out. In interviews, he explained that the situation wasn’t as simple as Kanye made it seem. He hadn’t intentionally disrespected Kanye, but rather, he had simply been trying to meet the demands of the industry—releasing his album on time and working with his peers. Big Sean wasn’t just hurt by Kanye’s words, but by the whole situation. A mentor turning on his mentee, calling him out in front of the world—it wasn’t just a bad business move; it felt personal.

Money Matters: The $6 Million Audit

As if the emotional fallout wasn’t enough, Big Sean’s financial situation with Good Music took a darker turn. When Big Sean’s career began to reach new heights, he started questioning how much money he was actually making from his music. His manager, who had experience working with some of the biggest names in the industry, suggested that Big Sean conduct an audit to make sure he was getting paid properly.

The results were shocking: Big Sean discovered that he was owed $6 million in unpaid royalties. While Kanye’s label, Good Music, was handling his finances, Big Sean soon realized that the money was going missing, and it was Kanye’s label that was responsible for mismanaging the funds. To make matters worse, Kanye himself was earning more money from Big Sean’s music than Big Sean was. It wasn’t necessarily Kanye’s fault—he might not have been directly involved in the financial mismanagement—but it painted a picture of a bigger issue within the label. Good Music was taking a substantial cut of Big Sean’s earnings, and it was clear that Big Sean was getting a raw deal.

While Big Sean didn’t immediately confront Kanye about the money, the financial revelations only added to the strain in their relationship. The respect Big Sean had for Kanye began to erode as he realized the ways in which he had been taken advantage of.

Healing or Moving On?

Despite everything that had happened, Kanye reached out to Big Sean at one point to try and mend their relationship. Kanye apologized—sort of. He said, “We did some things wrong,” but also made it clear that Big Sean had played his part in the fallout as well. Big Sean, however, wasn’t ready to forgive so easily. He rejected Kanye’s apology, citing that the damage had already been done. In his own interviews, Big Sean explained that sometimes, things just don’t work out, and this was one of those situations. He still loved and respected Kanye for all he had done for him, but the two were no longer close. They had moved in different directions, both professionally and personally.

The End of the Road?

So, where does that leave us? Kanye West and Big Sean’s beef is a stark reminder of the complexities of the music industry, where loyalty, money, and creative control collide. It’s also a cautionary tale about how sometimes, the people we admire and look up to can let us down in ways we don’t expect. For Big Sean, Kanye was a mentor, a friend, and a business partner—but in the end, their relationship soured because of miscommunication, unmet expectations, and, ultimately, a betrayal of trust.

While Big Sean has said that he still respects Kanye, it’s clear that the bond they once shared is gone. The tragic part of their beef isn’t just about what happened between them—it’s about how it could have been avoided, and how the fallout could have been different if both men had communicated better and supported each other through the inevitable ups and downs of their careers. As fans, we can only watch and hope that they one day reconcile, but for now, Kanye vs Big Sean remains one of hip hop’s most heartbreaking stories.