Kid Cudi Explains Why He Reconnected With Kanye West

Kid Cudi is opening up about his decision to reunite with Kanye West on stage during West’s recent Chicago concert, saying their nearly 20-year friendship is something outsiders may not fully understand.

West performed two shows in Chicago this week, with the second taking place Friday night and featuring several surprise guests, including Rick Ross, Travis Scott, Don Toliver and Kid Cudi.

Cudi’s appearance sparked criticism from some fans and commentators, including radio DJ Peter Rosenberg, who said he was disappointed by people who were “being openly lame about Kanye.”

Cudi responded on X, saying he understood Rosenberg’s frustration but stood by his decision to perform with West.

“I understand ur frustration Peter, I fucks w u, but I dont really care if ur disappointed in me,” Cudi wrote.

He explained that his relationship with West goes far beyond their professional connection.

“That man is my brother,” Cudi said. “U not family.”

Cudi said the two have shared almost two decades of friendship and artistic history. He also said that his conversations with West now feel similar to the early days of their relationship.

“Ive been around Ye, and I can honestly say talking to him now is how it use to be when I first signed to him, but even better,” he wrote.

West has faced intense backlash in recent years over a series of controversies, including antisemitic and pro-Nazi statements. In January, he published a full-page advertisement in The Wall Street Journal in which he apologized for and withdrew his previous antisemitic remarks.

Cudi said he believes people close to West should allow him room to move forward.

“Everyone deserves some grace when they family,” he wrote. “I was the hardest on him out of anybody. I held him accountable. He apologized and it was sincere.”

Cudi and West have had a complicated friendship over the years, with the two artists publicly falling out several times.

In a 2025 interview with CBS Mornings, Cudi said West had broken what he called “the code of a friendship.” He also acknowledged that the pair had attempted to repair their relationship before, only to fall out again.

One of their most public disputes came in 2022, after West criticized Cudi for being friends with comedian Pete Davidson, who was dating West’s former wife, Kim Kardashian, at the time.

“Just so everyone knows Cudi will not be on Donda because he’s friends with you know who,” West wrote in a since-deleted Instagram post, tagging Cudi and Kardashian.

Cudi fired back on X, accusing West of changing the story after they had already discussed the situation privately.

“We talked weeks ago about this. You’re whack for flipping the script and posting this lie just for a look on the internet. You ain’t no friend. BYE,” Cudi wrote.

Despite their turbulent history, Cudi now says the relationship has changed. For him, the reunion on stage was less about West’s public image and more about a friendship that has lasted for nearly two decades.

His message was clear: while fans and critics may have their opinions about West, Cudi believes he has his own reasons for choosing to stand beside someone he considers family.