While browsing through Kylie Jenner’s old Instagram posts, I found something unbelievable: Drake and Big Sean both performed at one of her parties. They spent the evening entertaining guests and showering Kylie with love and affection. Not many people can say they’ve had Drake give them his gold chain!
“You say in war he helped your baby’s mother’s mother. Yeah, that was hard, that was… hard. What’s going on? What does that mean? What does that mean? We were confused. You know what it means.”
Now, Kanye West has officially stepped into the ongoing drama with Drake, and things are getting wild. There’s a rumor that Drake’s questionable behavior goes way back, with whispers that he started making moves on Kylie Jenner when she was just 16. This whole saga kicked off when Kendrick Lamar dropped some bombshells in his diss tracks, accusing Drake of some seriously shady behavior, comparing him to R. Kelly and P. Diddy.
As if that wasn’t enough, Kendrick even hinted at some kind of secret PDF file operation happening at Drake’s mansion in Toronto. Fans have now gone into detective mode, digging into Drake’s past behavior with young women in the industry, from his young fans at concerts to Kylie Jenner. Drake’s list of creepy encounters seems to be growing longer by the day.
Kanye has stepped into the spotlight, dropping some truth bombs about Drake’s complicated history with Kylie Jenner. Rumor has it that Kylie’s mom, Kris Jenner, might have turned a blind eye to Drake’s alleged advances. There’s a lot to unpack here, so let’s break it down.
Drake and Kylie go way back. He’s been part of the Kardashian-Jenner inner circle for years, dating back to when Kylie and Kendall were kids. For Kylie’s 16th birthday in 2013, Drake, who was 27 at the time, attended her party and performed. He reportedly got quite close to her throughout the night.
Fast forward to 2019, Kylie and Drake sparked romance rumors when they were seen getting cozy at Drake’s 33rd birthday party. There’s some background to this drama. Drake and Kylie’s baby daddy, Travis Scott, were once close and even collaborated on the hit “Sicko Mode” in 2018. Drake was so excited about Travis’s success that he took to Instagram in December 2018 to celebrate “Sicko Mode” reaching number one on the Billboard Hot 100, calling Travis his brother.
In a now-deleted post, Travis echoed this sentiment on Twitter, saying, “Drizzy my bro man, since the back of a life this has been destined. Thank you.” Despite this brotherly bond, Drake did not invite Travis to his 33rd birthday party, although Kylie was on the guest list. This party took place just weeks after news broke that Kylie and Travis were taking a break.
An insider told People magazine at the time, “Kylie and Travis are taking some time but are not done. They still have some trust issues, but their problems have stemmed more from the stress of their lifestyles.” Despite assurances from Kylie’s inner circle that it was just a break, she attended Drake’s party solo on October 24th at Goya Studios in LA. Eyewitnesses reported that Kylie and Drake were quite flirty, with sparks flying between them. Kylie seemed very focused on Drake that night, spending most of her time near him and his friends. One insider told The Sun, “Kylie was rapping to his songs and dancing with her friends while she was next to Drake.” Although they weren’t dancing together, they appeared to have a strong connection.
A second insider confirmed to Us Weekly that Kylie and Drake were having fun together, laughing and enjoying each other’s company. “She seemed really happy and in a great mood, and she and Drake looked very comfortable with each other,” the insider shared. “There seemed to be an attraction there.” The rumors swirled for weeks until Us Weekly finally confirmed that Kylie and Drake were indeed a couple.
“Kylie and Drake’s friendship recently turned romantic,” one insider told the outlet. “At his Halloween party, they were affectionate and clearly together. They’ve been seeing each other romantically.” Drake also attended Kendall’s birthday party, and another source told Us Weekly that “Drake has always had a thing for Kylie.” But what do they mean by “always”? Since he first met her when she was 15 or 16?
Regarding Kylie, there were rumors that she was just playing around with Drake to make Travis jealous. An insider close to the KarJenner family told People, “Kylie doesn’t seem to be dating. She sees Drake occasionally, but it doesn’t seem serious. Kylie considers herself single. She has known Drake for a while. It mostly seems like they have chemistry, flirt, and hang out. Nothing too complicated.”
Just when everyone thought the situation couldn’t get messier, in March 2020, ET reported that Kylie and Travis were officially back together. But then, a few weeks later, Kylie was spotted out with Drake again, this time at a nightclub in Santa Monica. Even though they left separately, the rumor mill went into overdrive once more, with people speculating that Kylie might be stepping out on Travis with Drake.
As for Drake, he seemed to be enjoying the attention these rumors brought, whether there was any truth to them or not. Fast forward to May 2020, and he made headlines again by accidentally releasing a snippet of an unreleased track with Future, where he referred to Kylie as his “side piece.”
After facing backlash online, Drake issued an apology, claiming it was all a mistake. He explained that someone on his team accidentally played the unreleased track during Night Owl Sound’s IG Live. Drake wrote on his Instagram story, “A song that Mark played last night on Night Owl Sound live set shouldn’t have been played. It’s a song that leaked three years ago and was scrapped shortly after. He was just digging too deep into the Drake/Future catalog. The last thing I’d want to do is wake up having any friends of mine feeling disrespected, so I just had to say that to start off the day.”
While some folks were busy trying to figure out if Kylie Jenner and Drake were involved in something shady behind Travis Scott’s back, others were calling out Drake for being inappropriate. One fan said, “Drake calling Kylie Jenner a side piece on a song three years ago when she was 19 and he was 30 doesn’t sit right with me.” Others accused Drake of being a fake friend to Travis, with someone commenting, “Drake really a demon. How are you gonna be buddies with Trav and talk about Kylie Jenner as a side piece on a song with Future?”
Let’s not forget Kris Jenner’s role either. Looking at Kylie’s relationships with Drake, Tyga, and Travis Scott, it seems like Kris has been pushing her young daughter toward these older rappers. Kanye West even jumped in, claiming that Drake not only hooked up with Kylie but also with her mom, Kris.
This all started in October 2022 when Kanye posted on Instagram, saying, “Drake a f*** your baby mama’s mama. That’s real war.” People were initially confused, but soon Twitter users pieced it together, suggesting Kanye was hinting that Drake could be the father of Kylie’s second baby and also that Drake had slept with Kris.
When Kanye appeared on Drink Champs, they asked him to explain his post. While he didn’t directly address the rumors about Drake being Kylie’s baby daddy, he implied that Kris Jenner had hooked up with Drake behind her boyfriend Corey Gamble’s back. Kanye said, “You say in war he helped your baby’s mother’s mother. Yeah, that was hard. What’s going on? What does that mean? What does that mean? We were confused. You know what it means. So, and I put like Corey knows what it means.”
These rumors about Drake and Kylie have resurfaced due to recent allegations from Kendrick Lamar about Drake supposedly being a pedophile. Fans are urging people to take these claims seriously, pointing out Drake’s history of getting close to young women. One person wrote, “Y’all keep asking Kendrick for proof. We’ve seen this man messaging a 14-year-old talking about boy advice, weirdly celebrating Billie Eilish’s 18th birthday, following high school girls’ basketball players, the 17-year-old video on stage, and there’s probably more. He ain’t a pedophile, but a happy.”
Another added, “Let’s also not forget Drake planting that highly inappropriate kiss on Kylie’s cheek when he performed at her sweet 16, and he was 27.”
What do you think about these allegations of Drake getting close to Kylie and other young women? Is he a menace who needs to be held accountable, or are people blowing this out of proportion? Share your thoughts below.