Compulsively entrepreneurial, Jay-Z has transformed his love of sport into a business. This week his entertainment company Roc Nation revealed that it was branching into sports management. Its first client is New York Yankees baseball star Robinson Canó, whose contract is up for renewal at the end of this season.

Jay-Z, who grew up playing Little League baseball in Brooklyn, is a huge Yankees fan. But the venture is based on profit not sentiment. It will be Roc Nation Sports’ job to negotiate a whopping new deal for Canó. A 10-year, $254m contract signed in 2011 by Albert Pujols, a rival star, is the benchmark.

Such are the sort of sums the rapper deals in nowadays (“I’m all about the dollar bills that I make,” he once rapped). When he set up Roc Nation with the concert promoter Live Nation in 2008 he got $150m, including a $10m-per-album deal for himself. That too has entered his armoury of boasts. “I ran through that buck-50 Live Nation fronted me,” he bragged in a rap track last year. Translation: he spent it all.

Wild feats of profligacy are a crucial hip-hop pastime, one that Jay-Z performs with élan: he and his wife, the singer Beyoncé, reportedly lavished $200,000 on their daughter Blue Ivy’s recent first birthday party. But appearances are deceptive. Accumulating money fascinates the self-described “black Warren Buffett” far more than spending it.

The rapper, real name Shawn Carter, is the archetypal American rags-to-riches story. His unremorseful passage from Brooklyn crack cocaine dealer to corporate mogul might lack the pious trajectory of Andrew Carnegie’s escape from a dismal Scottish upbringing or Sam Walton’s journey from Dust Bowl poverty to Walmart plenty. But the affinity remains. That’s why he named his first record label Roc-A-Fella, after the great New York industrialist – and son of a lowly travelling salesman – John D. Rockefeller.

One of his most quoted aphorisms is: “I’m not a businessman, I’m a business, man.” But what sort of business is Jay-Z Inc?

The rapper sees himself as an insurgent, the black rebel capitalist “getting money up under you” – “you” being the white establishment. Key to his self-conception is the notion of the “hustler”. With a long tradition in African-American street lore, the hustler is the black urban equivalent of the cowboy, a solitary adventurer living by his wits in an OK Corral of NYPD squad cars, boom-bam beats, housing projects and gun-slinging rivals.

In his memoir Decoded he describes the hustler’s dream as “independence, wealth, and success outside of the mainstream’s rules”. A lot of vanity lies in his self-depiction as the hustler supreme, the smooth talker who hustled his way into Manhattan boardrooms. Friendship with Barack Obama hardly constitutes living “outside of the mainstream’s rules” either. But there is a degree of truth in the self-portrait.

The best hustlers (like the best sports players) rely on smoke-and-mirrors – gulling victims, outwitting opponents, staying one step ahead of the rest. As Jay-Z says in Decoded, “every hustler knows the value of a feint”. The same goes in rap. “So many people,” he writes, “can’t see that every great rapper is not just a documentarian, but a trickster.”

His music career is full of feints, such as his periodic claims to be retiring from the studio. Hits such as 2009’s “Empire State of Mind”, a modern standard, disguise the fact that his recent solo albums have been ordinary. Charisma and “uncontrollable hustler’s ambition”, in his words, ensure a golden glow of success suffuses all Jay-Z touches.

But look beyond the feints and tricks, and the Midas touch flickers. His three-year spell in the mid-2000s as president of Def Jam Recordings was mixed, with the emergence of two superstars in Rihanna and Kanye West, but also a number of flops. In 2007, the $204m sale of the clothing range he co-founded, Rocawear, propelled him up pop’s rich lists, which advertise him as being worth up to $500m. However, Rocawear, with which Jay-Z continues to be involved, has not thrived. Last year it laid off half its employees.

His vaunted co-ownership of the basketball team the Brooklyn Nets turns out to comprise an initial stake of $1m, a tiny fraction of the team’s worth. His publicised investment in the Barclays Centre, a new arena venue where the Nets play, amounts to about 0.2 per cent of the $1bn building. The real money comes from Russian oligarch Mikhail Prokhorov, who paid $200m for the Nets and has a 45 per cent stake in the new arena.

Jay-Z’s habit of teaming up with bigger partners extends to the new sports management agency, which has been formed with management behemoth Creative Artists Agency. Jay-Z’s participation has caused a blaze of publicity, but it is unclear precisely how much involvement he will have. More tricks, more feints?

The rapper has his critics. Chuck D, leader of Public Enemy, from an earlier, more radical generation of New York rappers, implied to the Financial Times last year that Jay-Z may be little more than a frontman. “I would say there are people behind him who have invested in him heavily,” the veteran firebrand said.

But Jay-Z should be seen as part of a subterranean but vigorous tradition of black capitalism; the efforts of individuals, in the face of entrenched hostility, to advance Booker T. Washington’s belief that: “At the bottom of education, at the bottom of politics, even at the bottom of religion, there must be, for our race, economic independence.”

Or, as Jay-Z raps: “Hustle hard in any hustle that you pitch.”