Who Is Cash XO & Why Did Drake Diss Him?

People who work behind the scenes often try to stay out of the spotlight. However, their modest popularity certainly does not diminish their importance and influence. One such figure is Cash XO, a luminary figure in the entertainment industry who manages one of music’s biggest stars, The Weeknd. While some are familiar with his name and works, a significant amount of people are unaware of who Cash XO is.

Following a name drop on Drake’s unconfirmed diss track, Cash’s name is currently making media rounds. Since the track was leaked, it has stirred up significant internet discourse. While the rappers Drake allegedly disses are easily recognizable, some listeners have wondered who the Cash he mentions is. Here’s a look at who Cash XO is, and why Drake supposedly dissed him. 

Cash XO’s Background

Cash XO was born Amir Esmailian on December 28, 1983 in Tehran, Iran. At the age of five in 1988, Esmailian and his family fled the country due to conflicts arising from the Iran-Iraq war. They eventually made their way to Ottawa, Canada, where Amir Esmailian was raised. Growing up, he enjoyed music like most people. However, there was certainly no telling how much of a big deal he would end up becoming in the music industry.

At the age of 19 in 2003, he got his first significant job in the industry. He was hired as the head of street promotion for Capital Prophets label, kickstarting his career before his twenties. By 2007, he stepped into a managerial role, serving as co-manager for Palestinian-Canadian rapper Belly. However, it was in 2011 that his life significantly changed after a friend shared some tracks by The Weeknd with him. Since then, Amir “Cash” Esmailian has built a reputable career and legacy with the singer.

What Does He Do?

As aforementioned, Cash XO first heard of The Weeknd in 2011. Soon after, he moved to Toronto, Canada to link up with the singer. Since then, Cash XO has managed the “Blinding Lights” singer and they have risen in the music industry together. They are both co-founders of XO Records which was established in 2012. In addition, Cash XO is a producer and songwriter. He has credits on songs by prominent artists, including The Carters, Future, and Travis Scott, among others. 

Speaking to Complex in 2017, Cash XO said, “I live, breathe, sleep, eat, shit XO.” That just goes to show his dedication to both The Weeknd and XO Records. For his work and undeniable influence, Cash XO has been recognized as a power player in the industry several times. He made it into Billboard’s “40 Under 40: Music’s Young Power Players” list of 2015. In 2024, he was also one of the names included in Billboard’s “Power 100” list. Cash XO is an important figure in The Weeknd’s life, and has been instrumental in his ascent. 

Why Did Drake Diss Cash XO?

Drake has had shots fired at him from multiple directions over the last few weeks. The rapper has caught smoke from Kendrick Lamar, Rick Ross, and ASAP Rocky. Surprisingly, on “All To Myself,” a track on Future and Metro Boomin’s WE STILL DON’T TRUST YOU, it seems The Weeknd also disses Drake. 

On April 14, 2024, an alleged Drake diss track titled “Push Ups” leaked online, leading to debates on whether the song is real or AI. However, since then, Drake has seemingly acknowledged that it was, indeed, his real response, even if it didn't land an official release.

On the song, the rapper took shots at everyone, including Cash XO. "Y'all nigga manager was Chubbs lil' blunt runner," he raps, suggesting that Cash once used to work under Drake's head of security. "Claim the 6ix and you boys ain't even come from it/ And when you got rich, you had to run from it," he continues, implying that, despite claiming Toronto, they didn't actually come up from the city nor did they stay once they saw further success. Then, he drops specific names. “Cash blowin' Abel bread out here trickin'/ Shit we do for bitches he doin' for n***as... Spend it like you tryna fuck, boy, you trippin', boy, you trippin'” he spits, alleging that Cash wastes The Weeknd’s money on other men. Obviously, Cash XO did not diss Drake himself. However, it’s no surprise the manager has been dragged into it as feuds are very often messy and without rules.