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The Criminal as Entrepreneur

Painting can do for the illiterate what writing does for those who can read.
                                                                    —Pope Gregory the Great

 Drug dealers anonymous / Y’all think Uber’s the future, our cars been autonomous.
                                                                    —Jay-Z, “Drug Dealers Anonymous

The latest iteration of rap beef—this time between the multiplatinum hitmaker Drake and the street-credible lyricist Pusha T—had all of the attributes of the tradition, only inart was fueled by the warp speed of social media and the glitz of a calculated marketing plan. Witty innuendo, gossip, and slick production were married to the Spotify playlist algorithm and Instagram stories. But there was something else at work in the reemergence of Pusha T, a forty-plus-year-old rapper who was the consensus winner in the battle. His open embrace of references to and imagery from the entrepreneurial aspects of drug culture brought a motif of the decades-old gangster subgenre in rap music1 back to front-and-center status. Pusha T relied on the artistic presentation of a black American antihero—the drug dealer MC (master of ceremonies)—a play on the transmutation of cultural capital that has accrued to both the street hustler and hip-hop artist who remain closely tied to their communities.

When Pusha T rapped on “If You Know You Know” that “A rapper-turned-trapper can’t morph into us / But a trapper-turned-rapper can morph into Puff,” he indicated a separation of sorts: an artist could never do what a street entrepreneur does, yet a hustler could not only make music but also conduct business at the highest level of the music industry (a nod to Sean “Puffy” Combs, whom Pusha described as the ultimate “street dream”). And by making clear that he didn’t care whether the average person understood the code he spoke, he (and the TMZ-destined, meme-worthy aspects of the back-and-forth) intrigued both those outside of the culture and people residing within those zip codes most familiar with “the life” he described.2 But why are such figures so intriguing?

The Celebration of Crime in Popular Culture

The celebration of crime is not a new phenomenon in American culture. David E. Ruth’s Inventing the Public Enemy: The Gangster in American Culture, 1918–1934 (University of Chicago Press, 1996) showcases the phenomenon as it played out a century ago. And Thomas H. Pauly, in tracing the evolution of the criminal throughout popular culture, describes the development of an image that makes the pure celebration or condemnation of criminal activity virtually impossible:

The criminal is the menace, the alien, the Other—the one we fear, avoid and condemn. Because criminals are outlaws, they operate outside of the rules and expectations by which we define ourselves as a society. But because they exist within our society, they threaten those codes that give our lives order and security. [But] we also realize that criminals are not always obvious outsiders. Some operate at the highest levels of respectable society and from very influential political and business positions. When this type of criminal ceases to be the random oddity and seems commonplace, our normal suspicions become confused and turn back upon themselves.3

Normalization of the street hustler, criminal, and gangster has been a staple of American pop culture, largely (it seems) because the lines between immoral and moral, informal and formal, illegal and legal have always been blurred.

In “Big Funerals: The Hollywood Gangster, 1927–1933,” a treatment of the image of criminal entrepreneurship, Andrew Sarris discusses the presentation of the “urban criminal” in cinema from The Musketeers of Pig Alley (1912) to The High Sign (1921) to Underworld (1927) to Little Caesar (1931) to Scarface (1932).4 “Crooks and criminals go back very far and down very deep in all cultures,” he wrote: “Cain as sinner rather than criminal because murder violated God’s law before there were any laws drawn up by men, The Thief of Bagdad, MacHeath in The Beggar’s Opera and later in The Threepenny Opera, Fagin, Bill Sikes, Raskolnikov, Smerdyakov, the denizens of François Villon’s Paris, the pirates, outlaws, highwaymen, and cutthroats of song and story. . . . The movie gangster drew from time to time on all these prior cultural sources.” With this in mind, Sarris determined, “The gangster movie was thus born full grown out of the union of mythology and sociology, literature and journalism.”5 That union—as it plays out across ethnicity, specific criminal activity and prohibition, legalization and decriminalization movements—suggests the superiority of art, at times, over politics in conveying popular sentiment in society.

It is the centrality of community sentiment and the shifts in it that explain why criminals are often popular. Black’s Law Dictionary defines crime as “an act committed or omitted, in violation of a public law, either forbidding or commanding it; a breach or violation of some public right or duty due to a whole community, considered as a community.” If a “community” finds a public law (or the motivation for it) more offensive than a committed or omitted act, however, or even sees public authority as less legitimate than its own customs and traditions, it stands to reason that the definition of “law” will not always be in alignment with the community itself. Should a “criminal” emerge who is seen as more faithful to the customs of the community, notwithstanding the standards of public law, he or she is likely to be more trusted than any central lawmaking or law-enforcing institution.

Perception matters, and in America kinship-based communities have often seen local, state, and federal governments in the light of Psalm 94:20 (“Shall the throne of iniquity have fellowship with thee, which frameth mischief by a law?”)—as entities with which they are incompatible, entities that even conspire against them, at times, through legal means. Inseparable from those perceptions, moreover, are the economic and entrepreneurial aspects of crime, and how they interact with community aspirations.

The Criminal as Businessman

Daniel Bell’s seminal 1953 essay “Crime as an American Way of Life” pursued greater clarity about the true relationship between crime, community, and culture.6 Crime, he suggested, “has a ‘functional’ role in the society, and the urban rackets—the illicit activity organized for continuing profit rather than individual illegal acts—is one of the queer ladders of social mobility in American life.”7 Bell argued that American organized crime could not be understood without an appreciation of “(1) the distinctive role of organized gambling as a function of a mass-consumption economy; (2) the specific role of various immigrant groups as they one after another became involved in marginal business and crime; and (3) the relation of crime to the changing character of the urban political machines.”8 To update that tripod, one may add a fourth category—the lens of artists and mass media.

Bell understood the centrality of gambling to the underground economy of his day. “Like American capitalism itself,” he wrote, “crime shifted its emphasis from production to consumption. The focus of crime became the direct exploitation of the citizen as consumer, largely through gambling. And while the protection of these huge revenues was inextricably linked to politics, the relation between gambling and ‘the mobs’ became more complicated.”9

The “mobs” organized around gambling sorted themselves along distinct ethnic lines. Among the poor and lower class, and black Americans in particular, gambling germinated in the policy racket and “numbers” game whereby participants bet upon the selection of certain numbers. How the disparity between black American numbers entrepreneurs and those from the Jewish and Italian ethnic groups played out can be seen in the takeover of the Harlem policy racket. In African American Organized Crime: A Social History (Rutgers University Press, 1997), Rufus Schatzberg and Robert J. Kelly describe this takeover as follows:

“Dutch” Schultz was a notorious gunman, widely feared in the New York underworld during the bootlegging wars. . . . [He] recognized the enormous potential of the Harlem policy racket. . . . Because policy was an African-American game, and illegal, and because the policy operators did not have a reputation for violence, a take over seemed relatively easy and not very costly, either in lives or in bribes. The Harlem “coup” could be conducted, therefore, through a series of staged incentives that appealed to the common sense of his African-American competitors. . . . Pitted against the New York crime bosses, Harlem seemed vulnerable. Harlem policy operators paid the police but they lacked a crucial advantage—the political machine. . . . More than removing law enforcement as an obstacle in criminal enterprises, Schultz mobilized police officers, bail bondsmen, lawyers, and court officials as active participants in his criminal enterprises and as appendages in his war for the numbers rackets in Harlem.10

This history represents an early example of the complexities surrounding the intersection of organized criminal activity, ethnic succession, and politics. Three of the most iconic black American figures historically tied to the numbers business are Casper Holstein, Stephanie St. Clair, and “Bumpy” Johnson. Casper Holstein, an immigrant from St. Croix, became the “numbers king” of Harlem early last century. Holstein is the real-life figure who serves as the basis of the character “Valentin Narcisse” on the HBO series Boardwalk Empire. Madam St. Clair, an immigrant from the French West Indies, was another Harlem boss who dominated the numbers racket. “Bumpy” Johnson, the enforcer for Madam St. Clair, later negotiated an agreement with Lucky Luciano—after Dutch Schultz was killed—to return control of the Harlem numbers racket to black operators. (Incidentally, considering her pioneering role as “Madam Queen” and “Lady Gangster,” it is surprising that a criminal entrepreneur such as Madam St. Clair has received so little attention as a figure of female empowerment.)

The importance of this form of gambling to the so-called legitimate economy was immense. Ivan Light wrote in 1977 that “Numbers racketeers have been the largest investors in black-owned business or ghetto real estate and the chief source of business capital in the ghetto. . . . Numbers bankers have been virtually the only sources of business capitalization available to local blacks lacking collateral or credit rating.” In addition, “numbers bankers have been leading philanthropists in depressed black neighborhoods, making donations to churches and athletic teams, and providing Christmas and Easter baskets for the poor.”11 Light views the numbers racket as an adaptation by blacks to address their inability to source and form capital from legal market and government sources. The numbers game in Harlem, the “Italian lottery,” and “Bolita” (popular among Cubans) are as much the ancestor of the modern lottery in America as those which existed during colonial times, but few are aware of this history.

All of these issues related to gambling continue to play out today, though legalization has changed, and continues to change, its economic and cultural implications. As Bell noted, criminal entrepreneurial activity declined when its consumption-based profile ascended, and the emergence of the legal lottery as a fundraising source for governments appears to have removed intrigue from the practice, although it clearly still exists underground. The marriage between live entertainment and gambling as a leisure activity contributed to the rise of the racetrack and the casino as physical locations. Casinos eventually won out, as horse racing faded in mass popularity, and boxing moved from outdoor arenas to become an event hosted in venues inside of or attached to casinos and their hotels. As these changes occurred, criminal entrepreneurs gradually receded because they were unable to compete on such a large scale.

More recent developments in legalization, however, may precipitate a shift in the opposite direction. When Bell was writing, the transformation of gambling paralleled the transition from an industrial to a consumption economy. Today, developments like the recent Supreme Court decision (Murphy v. NCAA) that effectively legalized sports gambling reflect the transition to an information economy. The legalization of sports betting in an era of social media introduces a new legal opportunity—the efficient transfer of increasingly valuable information. As Bell pointed out, the most important aspect of horse racing was not the outcome of the competition itself but rather the pursuit of accurate information in advance of it:

As other rackets diminished, and gambling, particularly horse-race betting, flourished in the ’40’s, a struggle erupted over the control of racing information.

Horse-race betting requires a peculiar industrial organization. The essential component is time. A bookie can operate only if he can get information on odds up to the very last minute before the race, so that he can “hedge” or “lay off” bets. With racing going on simultaneously on many tracks throughout the country, this information has to be obtained speedily and accurately. Thus, the racing wire is the nerve ganglion of race betting.12

Sports betting and its lucrative newswire should reward the combination of a detailed knowledge of sports and higher social media usage (notably, in this decade Latinos and African Americans have shown disproportionate engagement on Twitter and Instagram). With athletes disproportionately coming from lower-income communities—at a time when such communities have increased access to these celebrities—a greater flow of material information regarding factors that influence their athletic performance may be at the disposal of entrepreneurs from these communities. And since variables impacting athletic performance are not gambling-specific, space remains for individuals who specialize in information and data curation. The modern version of the “racing wire” appears to provide more opportunities for entry-level derivative monetization.

Another positive contributing factor in this direction might also be the increased importance of status-signaling through social media and the disclosure and transference of previously unknown information by rappers and celebrities. This was a factor in the Pusha T/Drake beef. It is widely believed, due to the fact that both artists (and Kanye West) have contractual relationships with Adidas, that Pusha T was privy to information about an upcoming marketing campaign the company was developing around Drake and his previously unknown baby son. Some pondered whether the disclosure cost the company untold millions by preempting the promotional effort and weakening Drake’s popularity. Others, though, saw it in terms of the publicity boost it gave to a company fiercely competing with Nike and holding off Puma.13 Nevertheless, the incident gave lower-income communities—generally more known for consumption—the kind of information that only well-heeled investors and company insiders would typically have access to.

Here, culture is not innovating; it is only continuing a long tradition of art serving the function of information provider. As decision-makers increasingly value intelligence, human and artificial, and as social media and the internet have democratized access to the distribution of information, those closest to poorer communities have more opportunity than ever to unearth insights, reveal gossip, identify trends, and exchange them for compensation.

The Oldest Profession

When Dave Chappelle held up Pimp, Iceberg Slim’s legendary book, during a 2018 Netflix special, and used an aspect of the narrative as a metaphor for his own career and American society, he not only struck a chord with his audience, he also brought one of the most popular personalities in urban street culture back to center stage. Iceberg Slim, born in Chicago in 1918, was the author of seven books during his lifetime, two of which were published posthumously. Pimp: The Story of My Life (Holloway House, 1967) was his autobiography, in which Slim details his career as a pimp from the age of eighteen to forty-two.14 Filled with gut-wrenching anecdotes, slang, and proverb-like sayings, the book has become more than a cult classic.

To observe leading black American comedians describing the impact that Iceberg Slim’s books about pimping, prostitution, and hustling have had on them is to witness the same reverence a devout believer displays for a sacred text. Chris Rock may have put it best, when interviewed for a documentary on Iceberg Slim (“Iceberg Slim: Portrait of a Pimp,” produced by rapper Ice-T) stating, “Those of us that know Iceberg Slim will put him with [James] Baldwin, Chester Himes, Richard Wright and Alex Haley. As the wrapped gift for every movie I’ve ever done, I give out copies of Pimp to the whole cast and crew. All the questions of life can be answered if you read this book.”

This sentiment, that the life story of a pimp could be the highest source of wisdom, is shared by many who place an accurate and dynamic recounting of the vicissitudes of life over a clear but static rendering of commandments. What some could not find in the stewarding institutions of their communities, they found in Iceberg Slim’s books Trick Baby (1967), Mama Black Widow (1969), The Naked Soul of Iceberg Slim (1971), The Long White Con (1977), and Death Wish (1977).15

As it relates to criminal entrepreneurship, Pimp fit neatly into a larger context surrounding the economics of prostitution. Generally, a lack of men in one ethnic community and a relative surplus in another is what has created fertile ground for prostitution on the streets of America. Ivan Light has analyzed this economy as it plays out, often in striking terms, across ethnic lines.16 Census data across three groups—foreign-born whites, Chinese, and blacks—showed the sex ratio for blacks moving further from a one-to-one correlation over the course of a century. In 1880, there were 97.8 black males per 100 black females, but that number was down to 92.2 black males in 1970. For Chinese it was 106.8 males per 100 females in 1880 and 110.6 males in 1970. For foreign-born whites the ratio of 115.9 per 100 in 1880 had gone down to 103.5 males per 100 foreign-born females in 1970.

The shifts in the male-female ratio impacted ethnic communities in dramatically different ways. Among black and Chinese communities (both of whom were disadvantaged in the legal economy), a white-patronized and ethnic-staffed vice industry emerged when sex ratio disparities were most pronounced in the late nineteenth and early twentieth century. As sex ratios normalized, however, demand for prostitution declined and vice entrepreneurs in both communities sought other pursuits. As Light put it:

For the Chinese, the decline of white-patronized vice encouraged the restaurant/tourist industry in Chinatowns. This shift was largely complete by 1940. It represents a case of industrial succession in which an illegal industry disappeared and a legal one replaced it. Among blacks, the decline of white-patronized vice resorts stimulated a parallel search for alternative revenues. In the period between 1920–1944, this redeployment began to take the form of a rudimentary nightclub industry, but race riots and juvenile street crime aborted the industrial succession after 1944. For both the Chinese and the blacks, therefore, a search for new opportunities arose in response to the declining profits of the white-oriented vice industry. But in the black case, industrial succession fizzled whereas in the Chinese case it succeeded.17

Today, the dislocations of the information economy and cultural shifts point toward new developments in commercial activity around intimate relationships. This will be largely because of three factors. First, there will be continued pressures on sex ratios. Second, the implications of changing legal and cultural norms also appear to open the door to the legalization of other intimate contract relations. And third, fiscally strapped municipalities desperately in search of new sources of funding may seek to exploit changing community sentiment around sex work.

Regarding the first, crushing student debt and increasing detachment from human contact (as a result of smartphone adoption, social media, and virtual reality) may be conspiring to create a generation of sexually frustrated people, particularly males, starved of human connection and touch. This results in a sex-ratio impact (though not exactly the same as that caused by immigration or natural birth outcomes). As debt burdens pressure women to delay marriage and childbirth, and very likely courtship and dating, while (nonaffluent) men are becoming less “marriageable,” the conditions that have historically been a boon to prostitution businesses are reemerging.

In addition, the advent of the much-discussed “incel” (involuntary celibate) movement raises another set of issues. Concerns linking terrorism to sexual frustration and “virgin-shaming” in the incel movement may spur policy innovation. As these discussions veer into tech-dominated issues around privacy and mental health, chances increase that interest groups will form to pursue policies around these matters. Some feel that surrogate partners may be a solution to the supply and demand problem, viewing intimate contact guided by counseling as a wellness regimen. The call to legalize medically assisted sex finds support within the libertarian community.

It is unclear what impact changes in law or culture—and any potential divergence between them—might have for criminal entrepreneurs. As seen in the case of gambling, or more recently in the case of marijuana decriminalization (discussed below), legalization does not always benefit those who succeeded in the industry as criminal entrepreneurs. Other countervailing trends are also at work. While the passage and signing of the fosta Act this year was celebrated as a means to fight online sex-trafficking abuses, its impact has been lamented by entrepreneurs increasingly wedded to ad monetization business models and those involved in consensual sex work.

Still, with Chappelle’s resurrection of Iceberg Slim, an assist from hip-hop (the complete literary catalogue of the author was acquired in 2011 by Cash Money Books, founded by mogul “Baby” and “Birdman”), and shows like HBO’s The Deuce, prostitution’s profile is rising in pop culture at the moment when economic and social changes are creating favorable conditions for commercial opportunities around it. Although it may not be “bad for business” (as Daniel Bell described reactions to prostitution in the 1950s), the celebration of the pimp is today complicated by other factors. #MeToo and the Women’s March, among others, have brought new attention to the abuse and harassment of women. In this cultural environment, it is more likely that women will have to feature more prominently in any visible expansion of the vice industry. The sequel to Pimp might be written by a woman—a consensual sex worker or someone involved in a nontraditional intimate relationship contract.

The Drug Trade

While industrial succession in gambling and prostitution did not materialize for blacks, ethnic succession opened the door to their participation in the drug trade. Describing a history that would later be echoed by a scene from the Godfather, in which the Five Families discuss keeping drug trafficking among “the dark people, the coloreds,” Schatzberg and Kelly write:

Unlike La Costra Nostra, Jewish, Irish, or WASP criminal syndicates, African-American criminal groups are locked out of many activities, including labor racketeering and loansharking; drugs, however, know no racial barriers. . . . The Vietnam War exposed many African-American soldiers to the heroin markets of the Asian Golden Triangle—the Shan States of Indochina, where opium is cultivated in the remote hills and other regions. . . . Partly as a result of the overseas experience, African-American crime groups were able to circumvent their Mafia patrons and buy direct from Asian suppliers.18

This increasing mobility (a staple of the movie American Gangster) and concentration within the trade gave the black drug dealer a position within street culture and the criminal entrepreneurial economy previously held by the pimp and the numbers trafficker before them.

Other trends lifted the Hispanic criminal entrepreneur: the Immigration and Naturalization Act of 1965, which enabled increased immigration from Latin America; Fidel Castro’s decision to send Cuban prisoners to America;19 and industrial succession which saw marijuana cultivation displaced by cocaine production in South America.

With Cuba serving as a distribution hub for the Colombian supply, and the Mexican drug cartel eventually seizing the Bolivian and Peruvian operations of Pablo Escobar when he died in 1993, a chain reaction was set in motion. Ultimately, Miami and Los Angeles became the key nodes of a supply chain ruled by Latino drug lords, with succession and population pressures contributing to racial tensions and even riots in the United States. By dissecting the business model of Pablo Escobar, as the Wall Street Journal did in its analysis of “Cocainenomics” (sponsored content to support the launch of the popular Netflix series Narcos) one gains an adequate understanding of the commercial paradigm.

The associated pop cultural paradigm can be seen in mass media’s fascination with Joaquin “El Chapo” Guzman today—both in rapper Fat Joe’s popular “Coca Vision” podcast (set in an El Chapo–style tunnel) and in the mandatory streaming drama series. The “El Chapo” storyline simply picks up where the Escobar archetype left off: drug sourcing in the homeland fuels both aspirational and ruthless criminal activity in the diaspora.

In the realm of pop culture, this pursuit of power and happiness can transcend ethnic affiliation in a uniquely American way, however, as when African American rappers champion and articulate the storyline of “others.” This tradition is well established in popular culture, where one group’s struggle can be “dressed in someone else’s ethnicity.”20

Miami-based rapper Rick Ross’s portrayal of the Colombian-to-Cuban and marijuana-to-cocaine succession over the course of his career is exemplary of this phenomenon. The “Rick Ross” persona is in fact based upon a real life African-American drug kingpin based in Los Angeles, “Freeway” Ricky Ross (the two have battled in court over the use of the name), who in the 1980s sold crack manufactured from cocaine distributed by immigrant Oscar Danilo Blandon.

The Justice Department’s description of Blandon lays bare the ethnic dimensions of a criminal-entrepreneurial power pyramid typical of the time (and one still seen today):

Oscar Danilo Blandon, a member of a prominent family in Nicaragua, fled to the United States soon after the Sandinistas came to power in Nicaragua in 1979. In the early 1980s, while living in Los Angeles, Blandon began distributing cocaine, originally at the behest of Norwin Meneses to support the Contra movement. Shortly after he began dealing drugs, Blandon began selling large quantities of cocaine on his own for his personal profit. By his own admission, he became a significant drug dealer, receiving cocaine from Colombian, Mexican, and Nicaraguan sources, and selling it to Ricky Ross and others in Los Angeles and elsewhere.

Just as one ethnic group voicing the experience of another does not always fit expectations, today the linear trajectories that one may expect in the drug trade do not always materialize. For example, whites and Hispanics are increasingly migrating to black neighborhoods in search of opioids like carfentanil, fentanyl, and heroin. The Miami Herald recently detailed the phenomenon as it plays out daily in Overtown, a black neighborhood in Miami-Dade County: “Most of the victims aren’t from the poor, predominately black community. They’re white and Hispanic users lured to Overtown by cheap packets of heroin known on the street as ‘boys.’ They can be had for as little as $10 at drug dens.” Whether “lured” or in voluntary pursuit, the scenario is similar to that witnessed last century when white males traveled to Chinese and black neighborhoods in droves, in search of prostitutes.

And as with other forms of criminal enterprise, legal and cultural changes around the drug trade have produced complicated effects. For instance, the gradually spreading decriminalization of marijuana has not yet translated into ownership of dispensaries, medical clinics, or publicly traded companies by those who dominated the business while it remained illegal. This can be attributed to many factors.

First, the lack of a seamless public policy mosaic where marijuana is concerned. Marijuana is still classified as a Schedule 1 drug and guidance on whether the financial sector can legally take deposits from its proceeds isn’t clear. While the Federal Reserve has given approval to a Colorado-based credit union that provides services to marijuana businesses, Chairman Jerome Powell wants Congress to clarify the matter: “This is a very difficult area because we have state laws; many state laws permit the use of marijuana and federal still doesn’t, so it puts federally chartered banks in a very difficult situation,” he told reporters during a June press conference. In addition, marijuana-related convictions have not been expunged on a mass level. As a result, criminal records still hinder previously incarcerated persons attempting to enter the legal economy.

Second, as with gambling, many new players began entering the game as laws were relaxed and cultural taboos faded (note the increasing number of songs promoting cigarettes as opposed to marijuana, and the perception that tobacco’s presence is growing in streaming shows and movies, as evidenced by a CDC study). When illegal entrepreneurial activities that rely upon trust fostered by kinship and community (even forced segregation) are legalized, criminal organizations that formerly dominated them may lose their underpinning of social cohesion, just as new competitors enter the market. Moreover, legalization tends to reward those who write the rules from dominant positions within governments. Contracts, police, and legislatures naturally protect incumbents from insurgents or outsiders. In effect if not necessarily in intent, marijuana decriminalization measures have been targeted to benefit middle- and upper-middle-class recreational users, not the communities most enmeshed in the drug trade.

For those communities, while the archetypal profession may have changed from prostitution and gambling to dealing, the criminal entrepreneur remains a central character. As before, the pop culture portraits of these figures are complex, with the criminal often serving as a role model, and even a teacher, to the larger community.

When Def Jam Recordings released an album and mini-documentary Music Inspired by Scarface in 2003, timed for the twentieth anniversary of the release of the 1983 movie (which itself was a remake of the classic 1932 film), it was only acknowledging what most within hip-hop and urban culture already knew: that no other presentation of pop culture had inspired as much slang, reenactment, lyrics, and concepts relative to the underground economy as this film. Not since the book Pimp had a piece of art become a shared metaphor for an entire culture. And in Tony Montana, young rappers and nascent entrepreneurs found a fictional role model, who provided a code, blueprint, and mindset for how to “come up” along the path of aspirational success.

Scarface, the legendary rapper who took his name from the movie, speaks in the documentary of how he identified with the immigrant’s journey: “I knew right then, man, if that dude could do it like that, man—just come over here with nothing and leave away from here, with everything—I knew for a fact, that that was for me.”

And Diddy punctuates that point with a collective claim on the character, “Tony, he was like a lot of us, backed up against the wall. He had to try and fight to make it in this world. That’s one of the reasons why minorities relate to it so much, especially black inner-city minorities. Drug dealing and drug selling was like one of the only ways we saw (as) an out.”

But a way out of what?

The Criminal Entrepreneur in Liberal Society

For some, “out” resembles economic liberalism—an individual search for prosperity and comfort, after years of poverty amid a suffering mass. In that sense mobility requires leaving the neighborhood. In her feature on Beanie Sigel’s “Remember Them Days” (2000), Eve sings: “Remember them days / Livin’ all days in doubt / Remember them days / Thinking there’s no way out . . . It’s all good now / We out the hood now.” But here leaving means finding opportunity in another marketplace, not moving away from a group of people. Rather, “the hood” is contextual, a way of life that has engulfed a community. It’s the same idea conveyed by Rich Homie Quan in “Back End” (2017), “I’m ’ah still count all my back end, I’m ’ah still do it for my fam. Just because I still got a lil’ money, that do not define the person I am.”

This is not the pure individualism of economic liberalism, yet it also remains a far cry from noneconomic liberalism. Noneconomic liberalism focuses on access to rights, liberties, and political equality from broader society, as opposed to specifically securing economic benefits. The Civil Rights Movement itself was largely a movement in the direction of noneconomic liberalism. Its emphasis was on ensuring a limited but guaranteed outcome (rights) rather an unlimited opportunity (income). Economics was a secondary goal; it was hoped that greater prosperity would follow from greater liberty and equality within society, and equal treatment from government. Economic interests—autonomy or establishing an equity stake in the national wealth distribution—were not pursued as ends in and of themselves.

The attitude of neighborhood criminal entrepreneurship, however, is distrustful of both markets and government, understanding both to be in the control of forces foreign to the community. Legalization of informal economic activity and its regulation by government has been seen as a threat to opportunity, particularly in segregated communities where kinship ties are the greatest source of trust. In this sense, criminal entrepreneurship, with its valuation of group empowerment, is much closer to the militant self-defense ideology of the Black Panthers, the cultural nationalism of the U.S. organization, and the “Do for Self” philosophy of the Nation of Islam than it is to the nonviolent resistance strategy of Dr. Martin Luther King Jr. and the Southern Christian Leadership Conference.

The criminal entrepreneur seeks access to government not to pursue parity within official society but as a means to protect business interests or achieve empire expansion. Again, the goal is economic benefit not civil equality. Bell described how ethnic succession in criminal rackets interacts with political authority:

The Italian community has achieved wealth and political influence much later and in a harder way than previous immigrant groups. Early Jewish wealth, that of the German Jews of the late nineteenth century, was made largely in banking and merchandising. To that extent, the dominant group in the Jewish community was outside of, and independent of, the urban political machines. . . . Irish immigrant wealth in the northern urban centers, concentrated largely in construction, trucking, and the waterfront, has, to a substantial extent, been wealth accumulated in and through political alliance, e.g. favoritism in city contracts. Control of the politics of the city thus has been crucial for the continuance of Irish political wealth. . . . The Italians found the more obvious big city paths from rags to riches pre-empted. . . . Many were fleeced by the “padrone” system, a few achieved wealth from truck farming, wine growing, and marketing produce; but this “marginal wealth” was not the source of coherent and stable political power.21

From this perspective, the Irish could generally be described as the most political community in their strategy to unlock opportunity and capital. The Jewish, the least. The Italian American community has occupied an interesting middle ground—first operating largely outside of formal political circles but then transitioning toward political power through figures such as Lucky Luciano and Frank Costello.

Black Americans, in their engagement of the political apparatus, most resemble the Irish, as affirmative action has unlocked contracts in numerous sectors. But their strategy—supplying votes rather than campaign finance (as the Italians shrewdly did) without articulating a business self-interest—has not been as effective.

Not surprisingly, the black community has met the harsh reality of ethnic succession in industry. Displaced after chattel slavery from the building trade professions in which they were skilled, and alternately ignored and taken for granted by the Republican and Democratic political parties, black Americans had to confront discrimination in unions and local governments controlled by white ethnic groups. What separated the black American experience in discrimination was that it was characterized by a denial of four of the five sources of capital: (1) access to financial markets, (2) retained earnings (savings), (3) some type of natural resources, and (4) government—with crime in deeply segregated neighborhoods allowing the most mobility in terms of trade and exchange with the broader society. Social cohesion through shared suffering created the basis for trust and the formation of capital, with assimilation on the basis of skin color almost completely impossible (the “passing for white” phenomenon is an exception). This was not the case for immigrants who graduated from “Italian,” “Polish,” “Irish,” and “Jewish,” designations into a “white” and even a fully “American” identity.

What hip-hop culture celebrates in the criminal entrepreneur maps more easily to the ethnic enclave than the free market or a multicultural government. The story arc that it most often identifies—adversity, climb, success—doesn’t culminate with a person transcending race, disconnected from the community from which they’ve come. Rather, the cultural definition of “success” is an individual who is rewarded for inspiring the group to travel the same path not toward atomization but autonomy. It merges economic and noneconomic liberalism while reconciling wealth redistribution and economic growth. The individual, no matter how successful is always connected to the group, like the diaspora to the motherland. It’s the value system expressed by The Carters (Beyoncé and Jay-Z) on “Boss” when Jay-Z raps, “Over here we measure success, by how many people successful, next to you / Here, we say you’re broke if everybody is broke, except for you.”

The Atlanta-based rapper T.I. offers a vision for economic development in his home city that epitomizes this approach. “I’m trying to build a community where the people within it can be proud. If they’re proud they’ll have more of a sense of wanting to maintain it.”22 And it embraces what Dr. Dre has in mind for Compton, what Nipsey Hussle intends for Los Angeles, and what Slim Thug desires for Houston.

For youth growing up in poverty, the criminal entrepreneur, as a work of art, may yield more applicable information than the public school system (which doesn’t teach economics or personal finance) and the university system (which they can’t afford to access). Continuing the tradition of art as information, there may be no greater evidence of how the educational vacuum can be filled than the work of personal finance expert Ash Exantus, whose book The Wake Up Call was inspired by Jay-Z’s 4:44 album. And Duane Lawton, before him, authored a three-hundred-page book covering twelve of Jay-Z’s albums, styling the lyrics as “street smart personal development advice.” Most poignant is the path of Curtis “Wall Street” Carroll, sentenced to 54 years to life, who studied the stock market and high finance and then promoted financial literacy to other prisoners.

After years of not only giving business advice but executing it, Jay-Z proves, for optimists, that the shift Bell identified—crime shifting its emphasis from production to consumption—is not permanent. Another shift in crime may be underway, via pop culture—this one from consumption to investment, in legal enterprise and continuing education.

From Criminal Entrepreneur to Community Development

When Pusha T raps on “The Games We Play,” “To all of my young n—s, I am your Ghost and your Rae / This is my Purple Tape, save up for rainy days,” he’s saluting the classic 1995 album Only Built 4 Cuban Linx . . . by Wu-Tang Clan member Raekwon. As Steve Huey said of that album in Tidal, it “translates the epic themes and narratives of a Mafia movie into a startlingly accomplished hip-hop album. Raekwon wasn’t the first to make the connection between gangsta rap and the Cosa Nostra (Kool G Rap pioneered that idea), but he was the one who popularized the trend. Cuban Linx’s portraits of big-money drug deals and black underworld kingpins living in luxury had an enormous influence on the new New York hardcore scene.”

That it did.

Less celebrated though, is Raekwon’s courageous follow-up album Immobilarity (1999), which champions the redemptive transition from criminal activity. In the album’s intro Raekwon states, “We have no interests nor investments in anything illegitimate. Don’t ever underestimate the power of forgiveness.” The true significance of the album’s theme is often missed. It was inspired by and embodies the essence of what KRS One raps about on “Drug Dealer” (1992)—pleading with the criminal entrepreneur to turn toward community development. Its focus typifies what the hit shows Power and Empire champion: the transition from drug dealing to successful entertainment enterprises.

Rather than embracing free markets or individual liberty, Immobilarity uncomfortably but quite accurately suggests the power of social cohesion and capital formation that arises from an immobile condition, and which gives birth to business activity in an ethnic context. Legitimate entrepreneurship, just out of the sight of government.

This vision represents not only the drug dealer MC as a work of art, it is potentially the apex of the criminal entrepreneur as both economic and cultural model. Raekwon, at a time when it wasn’t fashionable, went beyond the customary homage paid to mafia culture and opened the door to complete transformation. Nearly twenty years later, even with social trends on their side, few have matched the effort or walked through the door he artistically opened.

When references to Immobilarity join references to Cuban Linx, we may have a leading indicator of a synthesis on the horizon: the psychic income derived from an affluent lifestyle paired with the psychic income obtained from community development.

In a 1919 article for the Journal of Education, Gertrude Robinson described music as the most elemental of art forms, and described the transformative power it might have on those convicted of crimes. In words that clearly foreshadow the best of the drug dealer MC figure, she wrote, “Now modern sociologists are discovering another specific function of the most universal and the most simple of all man’s artistic impulses—the musical impulse. The sociological musician is coming to the aid of the criminologist. This is quite natural since the problem of reforming, not merely punishing, the anti-social member of society is a vital one in modern thought.”23

The aesthetic may not be to everyone’s liking. But for communities with disproportionate presence and influence in art and entertainment, there may be no more important force for development and growth than those persons who can make the lessons of crime not only rhyme, but reason.

This article originally appeared in American Affairs Volume II, Number 3 (Fall 2018): 167–87.

1 See the impact of Schooly D’s legendary song “P.S.K.” (1985).

2 To understand the criminal-turned-businessman metaphor, it is helpful also to recall the 2014 collaboration between Pusha T and Adidas on a “Black Market” sneaker described by some in media as “a crack colored tribute to the rapper’s hustling past.” Pusha ran to the interpretations, not from them, responding to GQ’s question about the inspiration: “Yeah I mean everything—the fish scale nuances, the cracked leather, everything—is inspired by street culture because I feel like I’m synonymous with that. Even the gum sole and the measuring line on the sole relates to that.”

3 Thomas H. Pauly, “The Criminal as Culture,” American Literary History 9, no. 4 (December 1997): 776.

4 Andrew Sarris, “Big Funerals: The Hollywood Gangster, 1927–1933,” Film Comment 13, no. 3 (May/June 1977): 6–9.

5 Sarris, 6–7.

6 Daniel Bell, “Crime as an American Way of Life,” Antioch Review 13, no. 2 (Summer 1953): 131–54.

7 Bell, 133.

8 Bell, 133.

9 Bell, 136.

10 Rufus Schatzberg and Robert J. Kelly, African American Organized Crime: A Social History (New Brunswick, N.J.: Rutgers University Press, 1997), 91.

11 Ivan Light, “Numbers Gambling among Blacks: A Financial Institution,” American Sociological Review 42 (December 1977): 898.

12 Bell, 137.

13 Mary Hanbury, “Rapper Pusha T Is Slamming Drake in a Feud That Should Thrill Adidas,” Business Insider, June 6, 2018.

14 Iceberg Slim, Pimp: The Story of My Life (Los Angeles: Holloway House, 1967).

15 Iceberg Slim, Trick Baby (Los Angeles: Holloway House, 1967); Mama Black Widow (Los Angeles: Holloway House, 1969); The Naked Soul of Iceberg Slim (Los Angeles: Holloway House, 1971); The Long White Con (Los Angeles: Holloway House, 1977); and Death Wish (Los Angeles: Holloway House, 1977).

16 Ivan Light, “The Ethnic Vice Industry, 1880–1944,” American Sociological Review 42 (June 1977): 464–79.

17 Light, 468–69.

18 Schatzberg and Kelly, 9–10.

19 Emilio T. González, “The Cuban Connection: Drug Trafficking and the Castro Regime,” Cuban Studies Association Occasional Papers 7 (1997).

20 As historian Neal Gabler, in describing the acting career of Muni Weisenfreund (who became Paul Muni), in his book (which became A&E documentary series) An Empire of Their Own: How the Jews Invented Hollywood wrote: “He came to Hollywood in 1929 and quickly won an Oscar nomination, but after a second film he returned to the stage. When he came back to Hollywood, starring in Scarface as a knockoff of Al Capone and in I Am a Fugitive from a Chain Gang, and later as a Frenchman in The Story of Louis Pasteur, a Chinese in The Good Earth, and a Mexican in Juarez, he assumed stature as one of Hollywood’s most distinguished actors. At the same time his career became a paradigm for the tortured identity of the actor Jew in Hollywood – always dressed in someone else’s ethnicity.”

21 Bell, 145–46.

22 Daryl Nelson, “T.I. Explains Why He’s Buying Back His Old Neighborhood: ‘No Fresh Produce, Liquor Stores,’” Atlanta Black Star, July 3, 2018.

23 Gertrude Robinson, “Music and Crime,” Journal of Education 89 (May 1919): 485.

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