After three weeks of going at each other’s necks on Complex’s "Everyday Struggle," DJ Akademiks and Joe Budden invited Lil Yachty as the morning show’s highly anticipated first guest on Tuesday. Budden has been critical of the Atlanta rapper on past episodes—he’s questioned his credibility and labeled him a rap troll—making their long-awaited face-off impassioned, if not productive. But the heated convo came to a record-screeching halt once the topic of recording contracts came up.

Joe asked Yachty whether he’d signed a 360 deal—an agreement that entitles a record label to portions of an artist’s every revenue stream—and, to paraphrase the great Doughboy, it seemed as if the Quality Control/Capitol artist don’t know, don’t show, or don’t care about the terms of his contract. A perplexed Lil Boat said he’s “heard about” 360 deals, but doesn’t know if he agreed to one. “I know I have an amazing deal,” he said, pointing out that he recouped a signing advance of more than $1 million. “I have an amazing attorney.”

The interaction got a bit awkward, especially after Yachty had been boasting about how his business game is sharper than that of his musical peers. But his unfamiliarity isn’t without precedent. (In fact, a 2016 Fader profile of Yachty raised questions about who controlled his publishing rights; however, Yachty tweeted earlier today that he does own his publishing.) There’s a long history of hip-hop artists who haven’t been well versed in the deals that determine how their money pie is sliced—situations that notoriously play out in favor of the label.

Perhaps the most notable example is N.W.A. The World’s Most Dangerous Group began its dissolution when Ice Cube departed in 1989 due to a dispute with manager Jerry Heller over royalty payments that he deemed unreasonable (they settled out of court). Dr. Dre, who co-founded Ruthless Records with Eazy-E, left the group in 1992, feeling he wasn’t being fairly compensated for his music and that he should’ve received additional profits for his role as a label head. “[Eazy] took advantage of me not knowing the record business back in the day,” Dre said in Ben Westhoff’s 2016 book Original Gangstas: The Untold Story of Dr. Dre, Eazy-E, Ice Cube, Tupac Shakur, and the Birth of West Coast Rap, suggesting that Eazy and Heller were in cahoots.

In 1985, Salt-N-Pepa—on the verge of becoming one of hip-hop’s marquee acts—signed a contract with Next Plateau Records that granted their manager Herby Luv Bug half of a $5 million check for production costs, while the group’s three members split the remainder. Herby was initially receiving 100 percent of the group’s royalties until they renegotiated years later. A decade later, TLC infamously filed for Chapter 11 bankruptcy—just after the release of 1994’s diamond-certified classic CrazySexyCool—due to a shitty 360 deal they signed with LaFace Records and the production/management company Pebbitone. New York Times broke down the specifics in a 1996 article:

TLC's contract with Pebbitone gives the group 7 percent of the revenues from the sale of the first 500,000 copies of the debut and second albums. That increases to 8 percent on sales over a million copies—a "platinum" seller. Even if the group stays hot long enough to justify an eighth album—a rarity in the genre—the members' percentage increases to just 9.5 percent on sales of more than a million copies. The royalty range in the industry varies from TLC's rate at the low end to up to 13 percent at the high end.

To be fair, it’s unclear whether Yachty is locked into an unfavorable contract. But it was alarming to witness the extent to which he seems uninformed about the particulars, especially given all of the historical hazard signs. Q-Tip told us “record company people are shady” on ATCQ’s “Check the Rhime” way back in 1991. The Lox’s We Are The Streets (2000) and Jadakiss’ Kiss Tha Game Goodbye (2001) both parody the reportedly unscrupulous contracts they signed with Puff Daddy’s Bad Boy Records, explicitly warning: “No matter how hard you try, after you sign, you cannot escape the rape.” Macklemore is woke, too. “Rather be a starving artist than succeed at getting fucked,” he rhymes on 2012’s record label takedown “Jimmy Iovine.”

The difference between today’s music industry and the wack deals of yesteryear is that the internet has allowed—and in some cases, forced—artists to be much more hands-on in their career’s management. At just 19 years old, Lil Yachty has done a great job of honing his sound and image. And it seems to have gone a long way, given his endorsement deals with Target and Sprite, and creative director role at Nautica. Hopefully, for his sake, the dividends will pay off fairly, and he’ll be fully informed next time he scribbles “Lil Boat” on a dotted line.