Big Sean & Kanye West: A Complete History

Historically, mentor-mentee relationships are a delicate proposition in hip-hop. While they usually start off harmoniously, it can be difficult to sustain them. Over the years, masters and apprentices that seemed almost symbiotic have seen their relationships swiftly turn to rubble. Other times, periods of estrangement will make it seem as though all is lost, only for them to reconcile down the line.

But in the pantheon of hip-hop mentorships gone awry, that of Big Sean and Kanye West is a unique case.

Where many of these signee/label boss dynamics present them as brothers, the dealings between Ye and the Detroit native seemed more transactional than most. While Big Sean grew to become GOOD’s most commercially successful artist not named West, there was always a sense that they weren’t hanging out on the weekends nor involved in each other's creative process too profoundly, if at all.

Now, 14 years after he signed on the dotted line with GOOD Music, Sean and Kanye’s partnership has gone from seemingly amicable to fractured and, in the mind of one party, entirely regrettable.

Long before they were trading shots, the origin of their relationship was aspirational in a way that feels near movie-script. Harboring dreams of rap stardom since his high school years, Big Sean seized upon the chance to confront his hero when he visited his native Detroit. After hearing from a friend that Ye was at a local radio station for an interview, the young MC seized his moment, and, as he told Hardknock TV, the encounter instantly changed his life.

"I was cashing my 100 dollar check that I worked so hard for. It was a Saturday so the line was hella long and my phone rings," Sean recalled. "He called me and was like yo man, you listening to the radio? Kanye down at 102… He was like, man you should go and just rap for him man. As he’s walking away I like, chase him down and I’m like yo man, can I just spit a 16 for you real quick as you walk out. He’s like I don’t really have time. I’m like please man, you my hero… I’m just rapping cause I knew it was my one opportunity."

It would still be two years before Big Sean would formally sign to GOOD, but the pair kept in touch, with Ye reportedly sending Sean beats to rap over and offering constructive criticism on what he did with them.  

"I wasn't signing acts at that time. But I was so inspired by what he did. His voice was very compelling.”"It was like out of the movies," Kanye said of their initial meeting. "I could hear his personality and character and style in it. He just walked up to me and said a rap and I said, 'I'mma sign you.'"

Rather than being the instant ascension to fame and fortune that everyone imagines, Big Sean has since revealed that his relationship with Ye started humbly. After Fat Joe estimated that Sean’s signing-on fee would’ve been around $50,000 during an interview, the Terror Squad icon, and the world, were collectively shocked when Sean conceded that "my first advance was $15,000, bro."

Despite the fact that he didn’t receive a lot of money upfront, Sean would soon prove his worth when, after a stream of well-received mixtapes, he dropped debut album Finally Famous in 2011. Officially launched by Ye at a star-studded listening party, the record was a hit and debuted at number 3 on the Billboard charts. 

At this juncture in his career, it seemed that Kanye was very much on board with Sean’s sound and they had a mutually beneficial relationship. With Sean playing a prominent role in GOOD’s famed compilation album, Cruel Summer, an interview with Big Sean saw him lay out their dynamic and express his admiration for West in one fell swoop. 

"As a crew, G.O.O.D. Music is taking it to levels that really haven’t been done collectively. Kanye is someone who knows how to make classic albums, a true thinker. He got me in the mindset of being a true thinker and always planning out every move you got going," Sean said, before continuing, "I used to be frustrated with Kanye all the time until I realized that he didn’t sign me for me to be up under him," Sean said of Ye pushing him to become self-sufficient. "He signed me for me to be my own artist. I learned that in a way of putting out my own music, putting out my own mixtapes, which I still believe in, which I got plugged."

Despite Sean suggesting that there had been times where he’d wanted Ye to be "more involved," the Detroit rapper revealed that West was "proud of him" when it came to the release of his sophomore record, 2013’s Hall Of Fame.

"He was jamming to it," said Sean. "There's always some things that we may disagree on, but as an artist, you just gotta roll with what you wanna roll with. He definitely respects that and supports me and I support him."

In spite of the pride that he felt, Kanye’s role in Big Sean’s career was to provide tutelage more than it was to actively shape his music. In comparison to other artists on the roster, the pair haven’t actually interacted a great deal since their collaborations on 2015’s Dark Sky Paradise.

During the course of his career, Ye played an active role in seven of the Detroit MC’s seventeen platinum-selling singles. But from the aforementioned record onwards, there was seemingly a distancing, whether from a production standpoint or as a guest, although Kanye was still named as an executive producer on Detroit 2, he wasn't actually on the tracklist. In the wake of this most recent album, Ye did publicly congratulate Sean, too.

Where a label boss will usually allocate some space on his records to provide a springboard for their artists, Ye-- who isn’t exactly frugal when it comes to giving out features on his records-- never called upon Sean to appear on anything on any of his solo releases (with the notable exception of MBDFT iTunes store bonus track "See Me Now").

While he initially seemed earmarked for an appearance on the cancelled TurboGrafx 64, no further attempts were made to give Sean some shine on a Ye record. Likewise, the plans for Sean to contribute to 2018’s slate of seven-track albums from GOOD were abandoned after the Detroit artist "wasn’t feeling the vibe."

Pusha T, John Legend, Kid Cudi, and even short-lived signee, 070 Shake, have all been given prominent placement on Kanye’s records, so thus it seems bizarre that in the ten-plus years that he was on the payroll, Sean was never deemed suitable for inclusion on an album.

However, Ye’s recent derogatory statements about his former signee would suggest that he didn’t necessarily respect his abilities or value his contributions to hip-hop in the way that you’d assume from a label head. 

Before the tail end of 2020, it’s unlikely that anyone gave the possibility of a rift between Sean and Kanye a second thought. After years of what everyone assumed to be peaceful co-existence, the first discernible seeds of discontent appeared to be sown during Ye’s campaign for ownership of his masters. After Ye proclaimed that he would return his 50 percent stake in their recordings to the artists on his roster. Sean enthusiastically proclaimed "thank you! This would help so much!"

Benevolent as this may have seemed at first glance, Charlamagne Tha God took issue and suggested that Kanye’s gesture belied the situation that he’d placed Sean Don in. 

"The restraint that Big Sean shows to Kanye West is remarkable," Charlamagne remarked in September of 2020. "It lets me know that he really is a healed individual because Kanye West— I hope one day Big Sean tells his story. Just know, Kanye West owes Big Sean a whole lotta money. And he got Big Sean in a very terrible contract to be out here screaming about giving folks their masters back and all types of other things." 

While Big Sean never formally confirmed or denied Charlamagne’s comments, acknowledgement of them seemed to come during his verse on Benny The Butcher’s “Timeless” in which he spit, "Signed a slave deal, now a n***a up, ownin' my master," before going on to say that there’s "labels that's up B’s that owe me M’s."

Although it caused a minor commotion at the time, nothing more was said on the matter until, a full calendar year later, Sean informed his audience that he’d be leaving GOOD in favour of his own imprint dubbed "FF To Def."

"By the way this the first project where I’m on my own label as well, no more lil dawg shit!!!!" Big Sean announced. "I bossed up! #DONLIFE."

When asked about his relationship with Ye by a fan, Sean insisted that it was "a forever brotherhood, but business wise, I had to start getting a bigger cut! I worked my way out that deal."

Rather than send his former signee well wishes on his new venture, things have apparently since turned sour. During an appearance on Drink Champs, Kanye harshly stated that plucking Sean from obscurity was the "worst thing" he ever did.

"I already decided that when I die, on my tombstone it’s gonna say: ‘I deserve to be here because I signed Big Sean," Ye said, much to the shock of N.O.R.E. 

Instead of solely revolving around music, the label boss revealed that there was a personal component to it, with Ye believing that he’d been the victim of disloyalty and ungratefulness at the hands of Sean. 

"I know this man mama, bro," declared Ye. "You know what I’m saying? I changed this man family and both John Legend and Big Sean when I ran for office got used quick by the Democrats to combat they boy that actually changed they life. That’s some sell-out shit and I don’t rock with neither of them and I need my apology. N***as is scared."

In response, Sean suggested that the man who he’d previously accredited with giving him "honest energy" was now being deceitful in his own right. "Was just with this man, he ain’t say none of that," Sean tweeted. "And this was after the interview! I’m dying laughing at you."

After a fan speculated that he owed him 3 million, Sean then tweeted and deleted that it was "more like 6."

With the battle lines drawn, some fans have speculated that the reference to "your circle shrinkin', see some boys escapin', rest of them is guilty by association," from Drake's "No Friends In The Industry" hinted at Big Sean’s departure. The Detroit MC has since suggested that his side of the story will come out and wryly teased his own appearance on Nore and DJ EFN’s show, declaring, "I can’t wait to go on Drink Champs now."

Left torn apart by the contractual side of the industry, Big Sean and Kanye’s shared history together was at once prosperous and yet still feels like a missed opportunity. Now left strewn to the wind, there’s no telling what could’ve manifested itself, both artistically and commercially, if these two ever locked in for a full project. But even if he may regret it,  Ye giving Big Sean a shot in that Detroit radio station created a superstar that is sure to have a fruitful career for years to come. With or without his friendship.