When Rick Ross first entered mainstream rap’s consciousness, it was the summer of 2006 and his first two singles were both blowing up the airwaves. Beginning with “Hustlin’” and its subsequent remix featuring Jay-Z and Young Jeezy – it was the release of Ross’ Scarfacesoundtrack-sampling second single, “Push It,” that really took his newfound celebrity to the next level. Rick Ross’ debut album, Port of Miami, would go on to sell 187,000 copies in its first week, and ultimately hit platinum status in 2016. But that was thirteen years ago. Fast forward to the present and it’s now been over two years since the release of Ross’ most recent album, Rather You Than Me, and nearly four years since Black Market, his worst-selling album to date. While the drop in sales isn’t a huge surprise due to the onset of streaming – coming off the two worst selling projects of his career, Rozay has a lot to prove with all that he has planned for 2019.

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Although he’s been relatively quiet on the music front as of late, aside from a look on Drake's latest, Ross has still found himself in the headlines, not for the best of reasons. Just last year Ross paid off a nearly $5.8 million-dollar tax debt to the IRS, was called out by his baby mama for not seeing his son in over a year, and suffered a heart attack. While Rozay has suffered seizures dating all the way back to 2011, in 2018 Ross was hospitalized and on life support for the reported heart attack. And according to his baby mama, Tia Kemp, the last time his son saw him was when he was unconscious in the hospital. Meanwhile, now that he has recovered and is seemingly back in good health (and continuously showing off his improvements on that end), Rozay has announced his first memoir, titled Hurricanes. The book, co-written with Neil Martinez-Belkin, will touch on “surviving the storms of life,” and is set for release on September 3rd.

Even if the name and music of Rick Ross has been less publicized in recent years, his influence remains all over the modern rap game. Take a look at the current rap charts right now and you’ll find a bevy of artists whose careers have in some way been influenced or impacted by Rozay, low key or otherwise. Whether it’s superstars like Drake, Meek Mill, and DJ Khaled, or newer faces out of Miami such as Kodak Black and City Girls – Rick Ross’ legacy may be in those artist’s hands more so than his own at this point in his career.

In an effort to both diversify his rap money and grow his business résumé, in 2011 Rick Ross bought his first Wingstop franchise in Memphis. A year later he was rapping on the Gucci Mane mixtape track, “Trap Boomin” – “I hit a lick and went and bought a Wingstop (Twenty of ‘em) / I sprinkle lemon pepper in that re-rock.” Not too long after, Ross stated on his remix of Lil Durk’s “Us” featuring Drake, “Them other boys well known for letting n***** starve / We eating good, not my 40 Wingstops.” Judging by these lyrics, Rick Ross went from owning a single Wingstop to 40 different locations in a year. However, according to a 2014 Forbes article, at the time Ross only owned nine locations. Then in 2015, Tech Insider reported Rozay now owned 25 locations, adding yet another a year later in Montgomery, Alabama; as well as his childhood Carol City, Florida location of Checkers in 2017.

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Regardless of the inflated numbers, it’s statements like these that have made the Miami rapper potentially more affiliated with the fast-casual chicken wing restaurant than music in this later-stage of career. Whether hip-hop fans are looking for a new teenage SoundCloud rapper or a mid-40s chickentrepreneur (see what I did there) remains unanswered, but the veteran rapper has clearly leaned into his investment as the unofficial face of the food chain – “Wingstop owner, lemon pepper aroma / Young, black n****, barely got a diploma.” 

In a 2018 interview, Wingstop CEO Charlie Morrison gave a lot of credit to the rapper’s investment/endorsement, saying: “He has a strong connection with our core consumer who is young, millennial, and follows Rick Ross and artists like him. He’s always very engaging and very supportive of the brand. He might be at a boxing match or one of his concerts or somewhere else and he almost always has a Wingstop cup in his hand. It keeps us relevant.” 

Outside of waning musical relevance, recent controversy, and chicken wings; what currently lies ahead for Rick Ross is Port of Miami 2: Born to Kill – the long-awaited follow-up to his 2006 debut album. At this juncture in his career, returning to his classic introduction to the rap game 13 years later is a wise move. The man hasn’t had a platinum album since, and among his eight other albums, it’s difficult to select a second record half as timeless as Port of Miami. Street singles, “Florida Boy” featuring T-Pain & Kodak Black, and “Port of Miami 2 Freestyle” have already been released in anticipation of the upcoming record release – the 10th studio album in his nearly twenty-year career. Will this be his best, and possibly final shot to claw his way back into rap’s upper echelon? Possibly. But in an attempt to hedge his bet, Rozay is also expected to release MMG Self Made Vol. 4, the fourth in the Maybach Music Group compilation series, before the end of the year.

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Even though the odds seem stacked against the man born William Leonard Roberts II, it’s nothing this big personality and big-bodied rapper can’t handle. A new classic album with one or two radio hits can easily right his ship’s course. Now we just sit back and watch it all unfold at midnight tonight, with a 10-piece of lemon pepper Wingstop wings and a bowl of sliced pears.

Do you think Ross is about to drop some major heat? Sound off in the comments.