What If “The Wire’s” Omar Little Was More like Woody Guthrie’s Pretty Boy Floyd?

Post-industrial Baltimore shares much with 1930s Oklahoma. In both places, people suffer(ed) from ecological, economic, political, and social disasters. Yet, Woody Guthrie managed to offer hope whereas David Simon’s worldview, though deeply powerful, feels desperately bleak. Simon’s passionate characters reveal the hard times of Baltimore’s downtrodden, maybe none more powerfully than Omar Little, who easily could fit into the Guthrie songbook. On Woody’s birthday (he would have been 104 today), let us ponder how Omar might have been more like “Pretty Boy Floyd,” a depression-era Robin Hood immortalized by Woody.

Omar proved one of the most fascinating and—perhaps shockingly—beloved characters on the critically acclaimed and immensely popular HBO television show, The Wire. His occupation was robbing drug dealers or “rip and run” in local parlance. He managed to live for nearly all five of Simon’s tour-de-force seasons before dying in a random if predictable manner.

Omar was, and remains, so popular because he was both compelling and refreshing. In some ways, his “life” was all too typical, an African American male born into poverty, orphaned, and then raised in the housing projects and on the streets of West Baltimore. Omar grew up, in the 1980s and 90s, around “the game,” the drug dealing and hustling many Blacks needed to play to survive. (Though from a more middle-class family, writer Ta-Nehisi Coates also grew up in West Baltimore.)

Sadly, Omar’s story was all too common. In “Across 110th Street,” Bobby Womack sang, in 1972, about the nation’s most well known Black ghetto, Harlem: “I’m not saying what I did was alright. Trying to break out of the ghetto was a day-to-day fight.” Omar, like Womack’s protagonist, represent the lived experience of many millions of other (African) Americans.

Simon added a brilliant wrinkle to Omar’s character by making him unapologetically gay. The show never shied away from his sexual exploits, with many scenes depicting him and his current lover passionately kissing. Omar frequently was insulted for his love of and lust for other men, especially by other Black men in “the game” who sought to prove their own masculinity by questioning Omar’s. Omar never shrank from his sexuality. He owned it.

He also owned the streets of West Baltimore. This gay man proved so dangerous and fearless that local kids would shout his name and run away at the mere sight of him strutting down a garbage-torn street or weed-choked alley wielding his signature sawed-off shotgun.

Another aspect of Omar’s magnetism was that he lived by a code of ethics that, to many,
seems perfectly reasonable. A drug-game variant on the golden rule, he only robbed from (and sometimes killed) drug dealers in “the game.” By contrast, he never targeted “citizens,” i.e. everyone else.

One of Omar’s finest moments—indeed, of the entire show—happened in Season Two, when he perjured himself in a Baltimore court of law with his testimony that resulted in a drug-gang hitman, Byrd, being convicted of murder. Byrd had no honor; he killed many people, citizens and dealers, but not the one in question. Omar willingly lied because a drug gang had murdered his lover but not before torturing him to punish and try to intimidate Omar.

In Omar’s riveting testimony, the lawyer everyone loved to hate, Levy, tried discrediting Omar by labeling him a “parasite” who threatened law-abiding citizens of Baltimore and contributed nothing to society.

Omar shot back that his vocation was no different than Levy’s! Levy was taken aback though viewers were not. Omar put a fine point on his parallel: “I’ve got a gun, you’ve got the briefcase.” The TV-viewing audience knew Omar had nailed it—spoken truth to power—for Levy dedicated his entire career to enriching himself by helping drug dealers and killers stay out of prison. Levy’s actions were far worse than Omar’s for Levy poisoned the very heart of American democracy.

While Omar’s insight—about the true parasites in our society—was hardly original, Omar’s delivery, straight off the streets, felt fresh.


Eighty years earlier, Woody Guthrie wrote much the same thing in his song “Pretty Boy Floyd,” declaring in one of the best and truest lines ever: “some will rob you with a six-gun and others with a fountain pen.” (I have no proof but it would not surprise me if Simon knew Woody’s song and updated it, brilliantly so.)

Like others Oklahoma-born and –bred, Guthrie suffered from the twin devastations of the Great Depression and Dust Bowl—one an economic catastrophe, the other environmental, and both caused by human greed. Woody put pen to paper and documented the humanity and struggles of those in his community, ordinary working people, and then added music.

Over the next two decades, Woody became the greatest songwriter of his generation—most notably “This Land Is Your Land.” Considered by many Americans to be the real national anthem, the song had several of its most overtly political stanzas (castigating private property as anti-human and expressing deep sympathy for the poor) “disappeared” when generations of school children grew up singing the Cold War version shorn of its political edge.

Among other Depression-era stories that inspired Guthrie were the exploits of Charles Arthur “Pretty Boy” Floyd. Floyd robbed banks across the Midwest in the early 1930s and became popular because he destroyed the mortgage papers at many of the banks he robbed. That is, Floyd liberated many citizens from their onerous debts. As a result, he was often protected by Oklahoma locals and earned the nickname “Robin Hood of the Cooksoon Hills.” Like the fictional Omar, Floyd’s fate seemed predetermined: gunned down by the FBI in 1934.

Guthrie compares Pretty Boy Floyd to an earlier noble outlaw, Robin Hood. Not merely criminals, outlaws possess some larger purpose that, at least to some, justifies breaking the law. Like Robin Hood, Floyd gained a following in Oklahoma because he essentially stole from the rich and helped the poor by destroying bank records. Floyd earned immortality thanks to Guthrie, who interpreted Floyd as an outlaw in the tradition of Robin Hood. (Here is Woody’s comrade Ramblin’ Jack Elliott covering the tune.)

…Many a starvin’ farmer
The same old story told
How the outlaw paid their mortgage
And saved their little homes.

Others tell you ‘bout a stranger
That come to beg a meal,
Underneath his napkin
Left a thousand-dollar bill.

Of course, the original outlaw, in the eyes of “known Communist” Guthrie and many others, was Jesus. Jesus was a worker, a manual laborer who earned his living in an honest manner and contributed to society: “Jesus was a man, a carpenter by hand.” Jesus also was a revolutionary who advised the rich: “You must take all your goods and give it to the poor.” Instead, as the story went according to Guthrie, “The bankers and the preachers they nailed Him on a cross. Then they laid Jesus Christ in His grave.”

In Guthrie’s hands, both Jesus and Floyd were outlaws, revolutionaries really, who attacked and condemned the rich in order to serve the people. Guthrie continued setting his sights on the master class, never more successfully than when he challenged the very notion of private property and boldly declared “this land is made for you and me,” the ultimate assertion of the commons.


Fast forward to Simon’s 21st century. These United States are a mess but, perhaps, nowhere more so than in its “inner cities,” including Baltimore, where poverty, racism, corruption, deindustrialization, pollution, and drugs converge to make life tragic and seemingly intractable. Every public or private institution, in The Wire, seems to be morally bankrupt with “leaders” unable or unwilling to stop the bleeding with capitalism at the rotting heart of the problem. As a result, most suffer but especially the poor and the Black, trapped in crumbling post-industrial edifices of former greatness.

In his critically acclaimed and wildly popular television show, David Simon dragged American pop culture into the nasty and noxious world where we now live, exploring many vital if depressing aspects of neoliberal political economy brilliantly delivered under the guise of a show about cops and drug dealers.

Numerous characters became beloved to viewers including: deeply flawed yet brilliant detective, Jimmy McNulty; homeless drug addict with a heart of gold and a desire to get clean, Bubbles, and; drug lord by day but community college student by night, Stringer Bell, who—had he been born White—would be running a Fortune 500 company rather than drug corners. And Omar Little.

Omar never was going to collect a pension. If he made 30, he would be lucky and he knew it. Everyone watching the show knew it. After all, he grew up poor and Black in West Baltimore. And he “chose” to rob drug dealers for a living, a career that he did so well. Actor Michael Kenneth Williams played him with such panache and charisma as to draw viewers into and embrace a character not obviously a crowd-pleaser.

Omar possessed the potential to become a Robin Hood figure much like Guthrie sang about, a working class outlaw in the tradition of Floyd—stealing from the rich in order to give to the poor. Omar proved, time and again, that money was not necessarily his primary or only motive. He had a profound sense of justice. Yet, ultimately, Omar was trapped in the game.

Omar embodied a larger problem with Simon’s vision. The show was utterly brilliant at laying bare the many complex problems—economic, political, racial, social—within the United States and world. However, he proved less capable of offering up solutions even when the root of the problem, capitalism, seemed so obvious. Sure, there are some good people who achieve small victories, here and there, but viewers were left, time and again, with righteous anger and little else.

Perhaps Simon’s cynicism, which risks sliding into apathy, IS the sign of our times. He is hardly alone. In his much-praised recent book, Steven Fraser labels modern-day America, “The Age of Acquiescence,” since the United States’ unprecedented levels of economic inequality have not resulted in any real pushback from the poor, working, or middle classes. Granted, one can see the stirrings of an uprising of the dispossessed in the immense popularity of Bernie Sanders’ insurgent political campaign or the impressive commitment and ingenious tactics of those in the #BlackLivesMatters movement.

Woody Guthrie’s vision was different than Simon’s. Woody used culture to attack inequality and injustice. Like Simon, a political artist extraordinaire, except Woody remained hopeful. When the United States joined World War II, Woody served in the US Merchant Marine (barely living to tell the tale after his ship was sunk by a German U-boat), and he continued to pen dozens of songs about inequality and justice.

And onto Woody’s beat-up guitar he emblazoned the following words that became so famous: “this machine kills fascists.” Indeed!

Was it too much to ask Simon to have shined some light onto the darkness of Baltimore’s and America’s other impoverished, urban neighborhoods? What if Omar’s gaze had risen above his ghetto streets to target the real enemies—the lawyers, corporate executives, financiers, politicians, and real estate developers who shut down the city’s steel and grain mills only to repurpose them into loft housing for young White gentrifiers? What if Simon had turned Omar into Pretty Boy Floyd? Now wouldn’t that have been illuminating!

Peter Cole is a Professor of History at Western Illinois University. He is the author of Wobblies on the Waterfront: Interracial Unionism in Progressive Era Philadelphia and currently at work on a book entitled Dockworker Power: Race, Technology & Unions in Durban and the San Francisco Bay Area. He writes on labor history and politics and tweets from @ProfPeterCole

Peter Cole is a professor of history at Western Illinois University. He wrote the award-winning Dockworker Power: Race and Activism in Durban and the San Francisco Bay Area and Wobblies on the Waterfront: Interracial Unionism in Progressive-Era Philadelphia, co-edited Wobblies of the World: A Global History of the IWW, and edited Ben Fletcher: The Life and Times of a Black Wobbly. He is the founder and codirector of the Chicago Race Riot of 1919 Commemoration Project.