Digging Into Drake's Cash Money Label Drama

Birdman and Drake attend Drake x Crown Royal x 5Ninth at 5Ninth on June 15, 2010 in New York City.

Jas Prince is the son of Pusha-T beef-slayer, J. Prince. In 2007 (or maybe it was 2006), Jas’ pops, the founder of Houston’s influential label Rap-a-Lot, suggested that his son find an artist of his very own. After some internet searching, the junior Prince found Drake’s MySpace page.

“I found him myself,” Jas recalled a few years later. “I sent him a message lettin’ him know who I was and that I wanted to work with him.” Right away, Jas thought that Drake would fit perfectly in Lil Wayne’s camp.

Not long after, Prince, according to a lawsuit he later filed, enlisted Wayne’s manager Cortez Bryant to “persuade Drake into entering an exclusive recording agreement and an exclusive management agreement with the two of them."

Later that same year, Bryant formed Aspire Music Group with his co-manager Gerald "Gee" Roberson and Derrick Lawrence. They then signed Drake to a management contract without telling Prince about any of it, he claimed.

The inevitable finally happened in mid-2009, when Drake signed to (wait for it) Aspire/Young Money/Cash Money, distributed through Universal after a significant bidding war.

By this time, a lot of water has passed under the bridge between Jas Prince and the people in Aspire. Jas’ original deal for a little over one-fifth of Aspire’s cut of Drake’s dough plus an additional 5% of the total went off the rails when Drizzy fired Bryant and Roberson in late 2011.

So, with everything in flux, Prince sued Aspire, saying they hadn’t been paying him his fair share. The years-long suit added Young Money to the list of defendants at some point, and was eventually settled in 2016 for a reported $11 million payout.

Drake’s 2015 surprise album If You’re Reading This It’s Too Late was released on Valentine’s Day, but it was no valentine to Birdman or Cash Money. The record, billed as a “mixtape,” was briefly available for free on SoundCloud before being taken down. There was rampant speculation that the album was a disillusioned Drizzy’s final one for Cash Money. That speculation was helped along by the fact that the project’s long list of thank you’s—all the way down to  "Amanda who took me to that poetry reading in Baltimore"—had no mention of Cash Money or the label’s head honcho Birdman.

The album’s “Star67” contained a line that many people considered to be a dig at Cash Money: "Walk up in my label like, ‘Where the check, though?’/ Yeah I said it, wouldn't dap you with the left, ho."

During an interview with Zane Lowe, Drake spoke on the ongoing legal drama between Birdman and Lil Wayne, and was notably gracious to both parties.

"I’m a person that’s very grateful for all the names that you mention, specifically Birdman and Wayne. I have a mutual respect for both guys. I pray that it works out,” he said. “That’s business, man. It’s a situation I pray gets resolved.”

Aspire sued Cash Money, Young Money, and Universal last year, claiming that the labels weren’t paying them their promised share of Drake’s profits. Aspire lawyer Jethro Eisenstein told Complex recently that the case is ongoing.

On Drake’s newest album Scorpion, the lyrics of “Is There More” (“Soon as the album drop, I’m out of the deal”) set off yet another round of speculation that Drake is disenchanted and ready to leave the only label(s) he’s ever known as a professional rapper. To be continued?