Six years ago, Shawn “Jay-Z” Carter found himself on the verge of finalizing one of the biggest deals of his life. The prize: A Jay-Z branded Jeep Commander that would roll off the lot boasting an audio system preloaded with all of Jay-Z’s songs, an interior swathed in butter-cream leather and an exterior slathered in a coat of patented Jay-Z Blue paint. For his efforts, the rapper would receive a 5-10% royalty on each $50,000 vehicle sold.
The Jay-Z Jeep would have been a multimillion-dollar bonanza had it ever hit the streets, but it fell through at the last minute. Through no fault of Jay-Z’s, a change of management at Jeep parent Chrysler iced the plans (the episode wasn’t reported until I stumbled upon it while reporting my new Jay-Z biography, Empire State of Mind). Those close to the negotiations say that the situation turned into a fiasco of epic proportions.
“That deal was the most [screwed]-up deal that I’ve ever seen or heard of,” says Michael “Serch” Berrin, the rapper-turned businessman who helped put together the Jay-Z Jeep proposal. “I came to Jay with the automobile industry in my back pocket to do a Shawn Carter edition vehicle that he approved, only to have the automobile industry basically shoot it down for fear that he was a bigger star than the car.”
Though Jay-Z is a perennial hip-hop Cash King, the eponymous Jeep is one of many deals crowding his entrepreneurial wastepaper basket. But listen to some of his work and you might get the impression that he’s never made a misstep in his life. He utters the phrase “I will not lose” in at least three different songs and constantly peppers himself with godlike monikers “Jay-Hova,” “Hova,” and “God MC” throughout his oeuvre.
In many ways, though, Jay-Z’s failures are more instructive than his successes, especially for people who aren’t lucky enough to be famous rappers.