Adidas said on Tuesday that it is cutting ties with Kanye West, ending what may have been the most significant corporate fashion partnership of the rapper and designer’s career after he made a series of antisemitic remarks and embraced a slogan associated with white supremacists that earned him widespread condemnation.

Adidas, which began collaborating with Ye, as West is now known, nearly a decade ago, after he left Nike, has long weathered public barbs from the rapper. Its partnership with Yeezy, Ye’s company, which encompasses sneakers and clothing, is estimated to be worth billions, making it among the largest sources of Ye’s wealth.

For Adidas, working with Ye gave the company a boost of creative cool and credibility that helped attract high-fashion collaborators like Gucci and Balenciaga.

“Adidas does not tolerate antisemitism and any other sort of hate speech,” the company said in a statement. “Ye’s recent comments and actions have been unacceptable, hateful and dangerous, and they violate the company’s values of diversity and inclusion, mutual respect and fairness.”

The company, based in Germany, said it would terminate the partnership immediately, end production of Yeezy-branded products and stop payments to Ye and his companies. The move was expected to subtract up to 250 million euros ($246 million) from the company’s profit this year, it said.

Over the past month, West tested the boundaries of acceptable behaviour even for a noted provocateur like himself. At his YZYSZN9 Paris Fashion Week show, he wore a shirt with the slogan “White Lives Matter”.