Digging Into Drake's Cash Money Label Drama

The number one stunna’s label and Canada’s biggest export have had many ups and downs in the past decade. Here are the key moments.

Drake Baby NYC
Image via Getty/Johnny Nunez

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

“Soon as the album drop, I’m out of the deal,” Drake raps on the Scorpion track “Is There More.” The shocking line seems to indicate that Drizzy’s record contract with Cash Money and its Lil Wayne-founded imprint Young Money—a deal that dates back to 2009—may finally be at an end.

There was plenty of speculation about this leading up to Scorpion, with industry insiders claiming that the project would conclude Drake’s eight-album deal with the label. That number hasn’t been confirmed, and there have been conflicting reports about which of the rapper’s albums would actually count towards the total. But no matter how you count it, it seems likely that Drake’s 2009 contract may finally be fulfilled.

Drake and Cash Money is a pairing that has not always been easy. There have been lawsuits, subliminal disses, and mysterious SoundCloud drops aplenty. Here are the highlights.

2007: The Most Important MySpace Page Ever

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.

2008: Jas Teams Up With Lil Wayne’s Manager

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.

June 2009: Drake Signs With Cash Money/Young Money

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.

July 2012: Jas Prince Sues Aspire

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.

February 2015: If You’re Hearing This, It’s On SoundCloud

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."

May 2015: “While They Was Skimming Off the Budget”

During a live show in Detroit, Drake fuels more rumors of label disenchantment with a freestyle: “Had niggas tell me to my face how we were family and how they love me/While they were skimming off the budget.”

April 2016: Nothing But Grateful

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.”

Fall 2016: “...and Nothing Else”

During a show with Lil Wayne, Drake pointedly said that he is Young Money “and nothing else,” omitting the fact that he is signed to Cash Money as well. At that same show, Weezy said “Fuck Cash Money” while Drake was onstage.

March 2017: Keeping the Lights On

On his More Life cut “Can’t Have Everything,” Drake said he was the one keeping his label afloat: “I mean, I keep the fuckin' lights on in the building/Man, my record deal should be 500 million.”

April 2017: Aspire Lawsuits, Continued

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.

Dec. 2017: Family Feud

In the final days of 2017, Lil Wayne put out a freestyle over JAY-Z’s “Family Feud,” with a guest verse from Drake. On it, Drake expresses dismay at how Wayne is being treated, though Drizzy notably does not mention Cash Money or Birdman by name.

“Tell me if TD Bank is approving loans/I'm thinking of paying Wayne what Universal owes/My nigga spent a lifetime going platinum and gold/He should own half of the label, shit out of control.”

June 2018: Out of His Deal?

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?

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