Jack Harlow Lost ‘A Lot Of Money’ Trying To Match Bets With Drake At The Kentucky Derby

Drake’s penchant for sports betting is becoming almost as well known as his biggest hits. Likewise, Jack Harlow’s admiration for Drake has become common knowledge. However, Jack recently learned the hard way that following in his hero’s footsteps isn’t always the best move.

During an interview with The 85 South Comedy Show he admitted that trying to keep up with Drake — who has a lot more money to blow at this stage in his career than Jack Harlow — lost him “a lot of money” recently at the Kentucky Derby. “I just told Drake I would bet what he bet,” he confessed. “So I copied him.”

Meanwhile, the two rappers have spent a lot more time together, vacationing in Turks & Caicos, visiting the Kentucky Derby, and of course, working on music. Their collaboration “Churchill Downs” — named for the Kentucky Derby’s famous racecourse — appeared on Jack’s new album, Come Home The Kids Miss You, after leaking early a week before its release.

That’s where knowing Drake came in handy; Jack shared the encouragement Drake gave him after the leak, which helped him put the disappointment in the past. Maybe the next bit of advice Drake can give him is how to turn his most recent faux pas, when he admitted to not knowing Brandy and Ray J are siblings, to his advantage the way Drake always has. Although considering his recent Instagram response to Brandy’s battle challenge, maybe he’s already getting some guidance in that respect as well.