Drake and Amari Bailey's relationship, explained: Inside the rapper's connection with Hornets prospect

Amari Bailey's NBA career may be just beginning, but he's already used to rubbing shoulders with the stars. 

He has been in the limelight from a young age after featuring heavily on the Lifetime series Bringing Up Ballers as a middle schooler. His mother, Johanna Leia, was one of four Chicago-area mothers who starred as she navigated the intense world of youth basketball as a single parent. 

After leaving middle school, Bailey played his high school ball alongside Bronny James at Sierra Canyon School in Los Angeles. A-list celebrities would often turn up to watch the team's games, including Michael B. Jordan, the Kardashians and Drake. 

Now, after an impressive freshman season at UCLA, Bailey is finally taking the step up to the pros. He was selected by the Hornets with the No. 41 overall pick in the 2023 NBA Draft, and he is competing for Charlotte at this year's Summer League. 

As it turns out, Drake's relationship with Bailey goes beyond just a fan watching on. Here's everything you need to know about the connection between the two.

Drake and Amari Bailey's relationship, explained

The world-famous rapper established a friendship with the talented young baller, even gifting him a custom chain. The diamond-studded accessory features the No. 10 from Bailey's high school jersey alongside the owl logo from Drake's October's Very Own fashion brand. 

 

 

 

 

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A post shared by Rap Direct (@rapdirect)

Bailey also posted images on Instagram of the two hanging out off the court, including this pair of photos from June 2021. At the time, Bailey was still in high school at Sierra Canyon.

 

 

 

 

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A post shared by @amari

Their relationship is rumored to be the result of Drake taking a romantic interest in Bailey's mother, Johanna Leia. The musician reportedly rented out the entirety of Dodger Stadium in Los Angeles to enjoy a private dinner with Leia along the third base line, which was captured by a Los Angeles helicopter reporter. 

Some have speculated Drake and Leia met at one of Bailey's high school basketball games. The two were seen chatting as Bailey competed in Sierra Canyon's regional semifinal matchup against Etiwanda on June 17, 2021. Sierra Canyon fell to a loss, but Bailey did drop 37 points. 

Drake’s sitting courtside for Sierra’s Regional Semi-finals and Amari almost caught a MEAN body just now. 😤 @SCanyonSports pic.twitter.com/18OV1oQhSH — SLAM HS Hoops (@SLAM_HS) June 18, 2021

However, rumors suggest any relationship between Drake and Leia was short-lived. The two have since moved their separate ways, and Bailey hasn't posted anything on social media with the rapper in about two years. 

MORE: Final 2023 NBA Draft big board: Ranking the top 60 prospects — and their pro comparisons 

Amari Bailey college stats

Below are Bailey's stats from his lone season at UCLA, which ended with the Bruins falling to Gonzaga in the Sweet 16.