From feuding with Kanye West to romancing Kylie Jenner, Drake has a complex relationship with the Kardashians
With rumors of a brewing romance between rapper Drake and billionaire makeup mogul Kylie Jenner, it is interesting to take a look at how the 33-year-old musician's relationship with the Kardashian family has developed over the ages.
Although everything seems to be all hunky-dory between Drake and the KarJenner clan at present, it was not always smooth-sailing between them, the main subject of contention being Kanye West.
Kanye and Drake have collaborated over a number of musical endeavors over the years, being on more or less cordial terms both personally and professionally, that is until last year when the Yeezy owner produced a song of the 'God’s Plan' rapper’s rival Pusha T, called 'Infrared'. An immediate feud started between Drake and Pusha T on social media, after which, the latter released a song called, 'The Story of Adidon' where he revealed that Drake secretly fathered a child, US Weekly reported.
After Kanye was blamed for telling Pusha T about Drake's son, the "I Love It" rapper publicly denied the claims. “I did not have any conversations about your child with Pusha,” he tweeted at the time. “I don’t play with the idea of people’s children after I spoke to Wiz [Khalifa] a few years earlier.”
However, Kanye's efforts to mend things with Drake flew out of the window after speculations arose later that month that Drake's reference of “Kiki” in his song “In My Feelings" was actually Kanye's wife, Kim Kardashian, whom he had sex with in the past.
“People making rumors or thinking you f—k my wife and you’re not saying nothing … that don’t sit well with my spirit,” West slammed back in an Instagram video at the time. “You know, if I had a girlfriend from Chicago, her name was Renita, and you was married to Rihanna, I wouldn’t make no song called ‘Riri.’ So when you’re like, ‘I don’t know where it came,’ you too smart for that bro.”
Bringing up Rihanna's reference in his angry response was a deliberate jab at Drake as he was once rumored to have hit on the "Diamonds" songstress shortly after she and Chris Brown called it quits.
Things between the two counterparts got further heated up in December of the same year when Drake said he was convinced that it was Kanye who told Pusha T about his son. “I tell him I’m having trouble with my son’s mother. We had a conversation,” Drake said at the time. “Oh this guy’s trolling me. This was like a manipulative, like, ‘I wanna break you’ thing. ... I said, ‘Alright, I’m gonna go back to distancing myself again. I know what this is.’”
Kanye fired back a couple of months later at Drake, claiming that the latter had tried to threaten him and his family. “So Drake if anything happens to me or anyone from my family you are the first suspect — so cut the tough talk,” West tweeted at the time. “You trying to be a bully. I never been bullied in my life and I never will be. That’s why I made it this far in a pink polo.”
The tension between the two died down (at least in the media) after that.
Then, days before news broke that Kylie was apparently seen striking a romantic "connection" with Drake at his 33rd birthday party, Kanye had some nice words for his former friend at an October 2019 interview with Apple Music’s Beats 1.
“I ain’t even thinking, I want all blessings for Drake. I’m an ordained minister, if he want me to like, when he finally get married I’ll show up and be like, ‘We’ve had our ups and downs!’(sic)" he said.
Neither Kylie, nor Drake has officially confirmed their relationship.