The "Keeping Up With the Kardashians" star also supported Blake Griffin at a comedy show he hosted to raise funds for his Team Griffin Foundation in Hollywood. In fact, during the event, Kendall Jenner was seen wearing Griffin's Ermenegildo Zegna coat over her shoulders as she sat beside other basketball players while Griffin was on stage. 

"Kendall was enthusiastic throughout Griffin's opening performance, but in the middle of a set by John Mulaney, she and several of the other basketball players went backstage," an insider revealed to People. Then, after Griffin was spotted hitting the town with a mystery woman the following January, his relationship with Jenner was rumored to be over and a source told People they were "cooling off."

After the split, Elle reported that things got awkward at sister Kylie Jenner's birthday party in 2018 when Kendall showed up with fellow NBA star Ben Simmons. "Kendall and Ben just breezed past Blake without saying a word to him," the outlet noted, with a source saying they "didn't interact at all" and that "it was awkward."

The following year, it appeared that Griffin took a jab at Jenner's family during the roast for Alec Baldwin on Comedy Central. Per the New York Post, he directed his remarks to Caitlyn Jenner, saying, "On behalf of the entire NBA and half the rappers on the Billboard charts, I want to thank you for giving your daughters their daddy issues."