“For those that think Hov’ thing is bling blingin’ / Either haven’t heard the album or they don’t know English / They only know what the single is, and singled that out / To be the meaning of what he is about / And bein’ I’m about my business, not minglin’ much / Runnin’ my mouth, that shit kept lingerin’ / But no dummy, that’s the shit I’m sprinklin’ / The album with to keep the registers ringin’ / In real life, I’m much more distinguished…” –Jay-Z, “The Bounce.”

On Sunday, June 16, during game five of the NBA Finals, the pop culture zeitgeist was dominated by the two teams participating in the series—the eventual champion Miami Heat and the San Antonio Spurs—and to a lesser extent, Kanye West’s latest album, Yeezus. Then, Jay-Z stepped in to interrupt our regularly scheduled programming. Hov and the good people at Samsung made a declaration, “We need to write the new rules.”

Since his official debut in 1996, Jay-Z has been a relevant cultural figure and arbiter of all that is trendy in mainstream Hip Hop. We’ve seen this from early co-signs of Cristal, $850 Manolo Blahnik Timbs, and more recently, “Rollies that don’t tick-tock.” Jay-Z’s lyrics have likely appeased companies like these, as well as impacted their sales. And even when things went sour with brands Jay gave his stamp of approval to (observe how shouting out Belvedere and Cristal respectively gave way to Armadale and Ace of Spades), he just changed gears and backed another brand.

As a fan of Jay-Z’s early work, I’ve watched his current ventures with RocNation Sports and his partnering with Samsung to give away one million free copies of Magna Carta Holy Grail. I’ve seen him applying the Jay-Z touch of formerly unpaid endorsements cloaked as trendsetting be applied to legitimate business ventures. And, if Jay-Z’s recent moves—direct forays into advertising and sports branding and unofficially campaigning for President Barack Obama to name a few—are any indication, I think he is now much more valuable as an ambassador for Hip Hop than a contemporary, competitive emcee.

Cashmere Thoughts: Jay-Z’s Early Brand Associations

“Fresh to death in Moschino / Coach bag / Lookin’ half Black and Filipino, fakin’ no jax / Got you a beeper to feel important / Surrounded your feet in Joanie Dega’s and Charles Jourdan…” –Jay-Z, “Ain’t No Nigga.”

I’ve always felt Jay-Z’s mission has always been the same. When he dropped Reasonable Doubt in 1996, it wasn’t about getting famous; it was about getting on top. His moneywise rhymes represented an authentic, artistic talent fostered by an upbringing in the Marcy Projects and a history of drug dealing. Singles from the album like “Feelin’ It” and “Dead Presidents” balanced mainstream inclinations with honest, personal expression. Similarly, On “D’Evils,” he famously asserted, “Nine-to-five is how you survive, I ain’t trying to survive / I’m tryina live it to the limit, and love it alive,” hammering home his money-hungry persona. Ingenuity, coupled with an all-star roster of contributing producers helped cement Reasonable Doubt as a notable release next to other albums in 1996, like Nas’ It Was Written and Tupac’s All Eyez On Me.

Back then, I don’t think Jay-Z was so much shouting out brands as he was trying to link himself via association with the upper echelon. I still remember when he had the umlaut above the letter A in his name. Rappers have been flossing since Eric B & Rakim were posing in Dapper Dan outfits. But, to me, it felt as if Jay was differentiating himself through the brands with which he was associated. Back on “Imaginary Player,” he boasted, “I gotta be like the pioneer to this shit, you know. I was popping that Cristal when all y’all niggas thought it was beer and shit…wearing that platinum shit when all y’all chicks thought it was silver and shit.”

True to his word, Jay was ahead of the pack in terms of flossing. If other rappers were wearing Rolexes, he was rocking an Audemars Piguet. If the competition was pulling up in Mercedes Benzes and BMWs, Jay brought out the drop top Bentley Azure. As the flossing and unofficial brand endorsements continued, I thought the lyrical introspection waned a bit. Jay-Z maintained steady popularity with singles reinforcing his lust for money and women, while still providing catchy beats and hooks. As a listener, the new approach felt vapid to me. But Jay continued to drop reminders that his plan was now a two-pronged strategy.

Show You How: Shawn Carter The Emcee & Ad Man

“I do this for my culture / To let them know what a nigga look like when a nigga in a roadster / Show them how to move in a room full of vultures / Industry is shady, it needs to be taken over / Label owners hate me, Im raising the status quo up / Im overcharging niggas for what they did to the Cold Crush / Pay us like you owe us for all the years that you hoed us / We can talk, but money talks, so talk more bucks… –Jay-Z, “Izzo (H.O.V.A.).”

I always found it interesting that one of Jay-Z’s more profound lines about Hip Hop’s history and his place within it was buried in a shallow hit like “Izzo (H.O.V.A.).” On the most basic level, the single was a commercial success; it peaked at the #8 spot on Billboard magazine’s “Hot 100” while in the midst of a 20-week run. On the other hand, this was Jay-Z’s case for increased cultural relevance. I thought it was Jay explaining that he wasn’t just amassing wealth for sport as if he were Donald Trump. He links himself with The Cold Crush Brothers, who were one of Hip Hop’s pioneering groups. But the vast majority of people outside of Hip Hop weren’t (and still aren’t) familiar with them. Part of that is because Big Bank Hank of the Sugarhill Gang stole some of Cold Crush member Grandmaster Caz’s rhymes and used the unaccredited bars on “Rapper’s Delight.” But part of their lack of recognition and commercial compensation was also rooted in a bitter label dispute between Tuff City and Profile Records, which stunted the sales of their 1984 hit “Fresh, Wild, Fly & Bold.” So I thought Jay-Z was trying to toe the line between establishing and maintaining an amount of cultural significance while assuring that he didn’t get financially cheated like so many of Hip Hop’s founding fathers. This was something we saw pre-Blueprint on singles like “Come And Get Me,” but it appeared more frequently after “Izzo (H.O.V.A.).”

Fittingly, another thing that appeared more often in the post-Blueprint era was official brand endorsements. The talk of Belvedere vodka–the brand Jay name checked on songs like “Get Your Mind Right” and “Fiesta (Remix)”–gave way to Armadale. Since Roc-a-fella bought the domestic distribution rights to the Scottish vodka in 2002, it only made since to plug the in-house brand. Roughly two years later, Jay-Z signed an endorsement deal with Reebok’s RBK division for an undisclosed amount. To me, the release of the Reebok S. Carter shoe marked one of the moments where Jay-Z not only understood his power as a trendsetter, but he also harnessed that power to boost his net worth. These were the kinds of moves that forshadowed the 2008 partnership between Jay and Steve Stoute as co-chairmen of Translation Advertising. Again, I can’t say I was as much of a fan of the music from that era, but I can say I definitely understood there was a plan in place. What was Jay-Z’s ultimate goal though?

Moment Of Clarity: Jay-Z’s Artistic Reincarnation

“I dumbed down for my audience to double my dollars / They criticized me for it, yet they all yell ‘holla’ / If skills sold, truth be told, Id probably be / Lyrically Talib Kweli / Truthfully I wanna rhyme like Common Sense / But I did 5 mill, I aint been rhyming like Common since…” –Jay-Z, “Moment Of Clarity”

I think the above bars, on what I and many others feel was Jay-Z’s last album of worth–The Black Album–lay out the strategy. All subsequent works showcased a noticeably slower, deliberate flow and rhyme scheme, and many critics felt things sort of bottomed out with 2006’s Kingdom Come. If you subscribe to the theory that Kingdom Come was Hov’s lyrical nadir, then it may have been the beginning of his financial apex. By the time Jay-Z channeled Michael Jordan circa 2002 with his grand comeback to Hip Hop, Fortune magazine estimated his net worth at $320 million. Previously, Jay had hinted at the notion that his “death” in the 2004 music video for “99 Problems” was in fact a depiction of his artistic reincarnation. But if that wasn’t clear enough, I thought his infamous line, “I’m not a businessman, I’m a business, man” from the remix to “Diamonds From Sierra Leone” certainly was. Jay-Z evolved from being a trendsetter, to a bona fide pitch man. Reebok gave him a shoe, Def Jam temporarily gave him the presidency of the label (along with the masters to Reasonable Doubt) and Budweiser gave him a lucrative check to become the co-brand director of Budweiser Select. There was nothing under the table about those deals.

While songs like “Moment Of Clarity,” “The Bounce” and “Come And Get Me” hinted at it, I thought Jay-Z had a very direct, two-tiered approach to the second half of his career. I think that somewhere in between The Blueprint and The Black Album Jay-Z made a conscious decision to focus more on net worth, cultural impact and branding than lyrics. The tradeoff was that Jay could use his wealth and cultural capital to further promote the culture of Hip Hop and fund social initiatives instead of being a socially conscious rapper. As for the rhymes, he could pick and choose the times when he wanted to tap back into the intricate Reasonable Doubt style, subject matter and delivery.

To me, the question becomes how do you quantify the influence of emcees like Talib Kweli, Common, dead prez or others that have been tabbed with the conscious label? I don’t know. But I do have a rough idea how you quantify the influence of someone with 12 number one albums and a net worth that Forbes.com estimates at $450 million. The latter is a person who can repeatedly and openly admit to selling crack yet still help an incumbent senator become president by adding a bit of cultural cache. I don’t think you can be featured on terrible but profitable songs for charitable causes alongside U2 members such as “Stranded (Haiti Mon Amour)” without that post-Blueprint shift. And while I’d admit that Jay was definitely self-serving at points, few people have eloquently (and popularly) articulated the case for Rap as poetry the way Jay-Z did on the Dream Hampton-assisted Decoded. Like them or not, I’m not sure those moves are even possible if Jay-Z doesn’t water down his flow for mainstream consumption and keep ringing up hit singles and number one albums. Was it worth it? Could a more lyrically intricate emcee have made the same moves? How do we compare the cultural value of a song, such as will.i.am’s “Yes We Can” or Young Jeezy’s “My President” against Jay-Z and Beyonce palling around with President Obama as he brushes the dirt off of his shoulders. I don’t have an answer for that.

I Did It My Way: Assessing Jay-Z’s Real Value

“I made it so, you could say Marcy and it was all good / I aint crossover I brought the suburbs to the hood / Made ‘em relate to your struggle, told ‘em bout your hustle / Went on MTV with do-rags, I made them love you / You know normally them people wouldnt be fuckin with you / ‘Til I made em understand why you do what you do / I expected to hear, ‘Jay, if it wasnt for you’ / But instead, all I hear is buzzing in your crew…” –Jay-Z, “Come And Get Me.”

As we’ve seen previously on Rick Ross’ “Hustlin’ (Remix)” and Big Boi’s “Flip Flop Rock,” dumbing down one’s flow has its disadvantages too. When in lyrical cruise control, sometimes it’s difficult to turn that proverbial off switch back on. Back in March, listeners waited for a much-hyped collaboration between Jay-Z and Kendrick Lamar. I’m among those that believe K.Dot lyrically ran circles around S dot Carter, but few seemed to care at that point. The artwork for “Bitch Dont Kill My Vibe (Remix)” featured Michael Jordan and Kobe Bryant on the court together. But it may as well have been a screen shot of a rookie Allen Iverson crossing Jordan over at the top of the key. I think the reason why is pretty clear to most of us. At this point, Jay-Z is more valuable as a cultural arbiter and ambassador for Hip Hop than a contemporary, bar-for-bar, competitive emcee. He’s far from the point where he can only be paraded out for the latest edition of VH1’s “Hip Hop Honors.” And I think he’s too smart to let that happen anyway.

I feel, by accumulating an impressive catalog of hit records, having owned a share of the Brooklyn Nets, and even campaigning with the President, Jay-Z has accomplished as much as he could as a rapper. So it makes perfect sense that he, the businessman with a constant itch for more, would move his first love to the side in favor of something new and exciting. Also, as part of this new partnership with Samsung, Jay appeared in a commercial with Timbaland, where he loosely alludes to “rewriting the rules,” albeit with regards to his becoming an agent, or by giving away one million copies of Magna Carta Holy Grail–an unprecedented move by an artist of any genre, while simultaneously setting it up for even more sales.

I’m reminded of that moment on the Dynasty Roc La Familia “Intro” where Jay-Z called himself “Stevie Wonder with beads under the do-rag.” In the 13 years between then and now, Jay has essentially tried to be both Stevie Wonder and Berry Gordy. But as Jay’s turn next to Kendrick (or even next to a sober, more focused Lil Wayne circa 2004) showed us, there will always be emerging artists vying for the title of “Best Rapper Alive.”

What there may not be–at least for the foreseeable future–is a rapper capable of rubbing elbows with the President of the United States, helping Kevin Durant, Skylar Diggins and Robinson Cano boost their Q-rating, lunching with Warren Buffett, bringing Oprah Winfrey to the projects, hopefully schooling Gwyneth Paltrow on the correct time and setting to drop any iteration of the n-bomb (hint: never), and eloquently explaining the nuances of Hip Hop music and culture better than most of the talking heads on CNN, all while possibly notching a record thirteenth number one album.

Billboard Editorial Director Bill Werde has already indicated the one million copies of Magna Carta Holy Grail freely released to Samsung users July 1, won’t count as sales. This comes despite the fact that Samsung allegedly coughed up $20 million plus up to another $7.5 million in music rights and endorsement fees for the album.

“The ever-visionary Jay-Z pulled the nifty coup of getting paid as if he had a platinum album before one fan bought a single copy,” Werde wrote in the June 29 edition of Billboard. “(He may have done even better than that—artists generally get paid a royalty percentage wholesale. If Jay keeps every penny of Samsung’s $5 million purchase price, he’d be more than doubling the typical superstar rate.) But in the context of this promotion, nothing is actually for sale.”

All of which means we shouldn’t expect a ton of substance behind RocNation Sports or Magna Carta Holy Grail. But I do think they’ll both have significant cultural and financial impact and be profitable. The fact that folks have been talking about Jay-Z and Samsung for the last few weeks means they’ve both already won. I don’t think it’s disrespectful to call Magna Carta Holy Grail one long commercial for Jay-Z and Samsung. The album’s actual commercial debuted when the NBA Finals put up a 12.0 overnight rating. According to Nielsen, those are the highest ratings since the 2004 series between the Los Angeles Lakers and the Detroit Pistons. So this landmark deal between Jay-Z’s camp and Samsung has already made its mark. And if we’re lucky, there will be some actual substance on the album too.

Additional reporting by Homer Johnsen.

Omar Burgess is a Long Beach, California native who has contributed to various magazines, newspapers and has been an editor at HipHopDX since 2008. Follow him on Twitter @OmarBurgess.