The Bogeyman of Baltimore’s Drug Trade: Remembering Omar Little

Omar Little, played by the late Michael K. Williams, and his crew live for one thing and one thing only: robbing drug dealers. In the first three seasons, they have a personal vendetta against the Barksdale Organization, but we’ll get to that in a moment.

They later take on Marlo and the Stanfield Organization and score the ultimate heist by robbing the entire New Day Co-Op, which was basically a collaboration between all the top drug dealers in Baltimore. Omar and his crew were definitely about their business, but they’re not in the business of hurting innocent citizens; only those involved in the drug trade are on their hit list.

Omar is the king of the stick-up game because he’s not just fearless; he’s also a master planner and a natural leader. He’s not afraid to put in the long hours of surveillance work that most people would run from. He’s always watching and waiting, like a lion stalking its prey. And, let’s not forget his reputation—it’s so intimidating that most of his victims don’t even think about putting up a fight.

While Omar wasn’t the main protagonist of the story, he definitely helped carry the show to be one of the greatest in television history.

Omar’s crew is a rag-tag group of Baltimore hoods who are all in it for the thrill and the cash. And let’s just say they’re not your typical run-of-the-mill robbers; many of them happen to be LGBT individuals who bring their own unique flair to the heists. With Omar leading the charge, they’re a force to be reckoned with, and all the dope boys and drug bosses don’t have a choice but to respect him.

He is the ultimate Baltimore bad boy, known for his fancy stick-up moves and his love for whistling “A Hunting We Will Go” as he robs drug dealers. He’s the ghetto Robin Hood of the streets, sort of, taking from the rich (drug dealers) but keeping the money for him and his crew.

His whistling was more of a warning to any of the dope boys within earshot; drug dealers throughout the city fear and loathe him for his well thought out heists that leave them high and dry. He’s the ultimate thorn in their side. If you were a corner boy and you heard that whistle, you knew you either needed to run or prepare to be in a gunfight with one of the best who ever did it. There were a bunch of scenes where you could hear “Omar’s coming!” as he strolled the streets with his shotgun whistling. You would see everyone scrambling to get away as if the bogeyman himself had just appeared.

In contrast, his moral code keeps him on somewhat good terms with some Baltimore police. His bold robberies make him a hero amongst neighborhood kids, and he proves to be one of The Wire’s characters with integrity and intelligence, including those who make mistakes but own up to and learn from those errors in judgment. His moral code is what I think makes him such a great antihero. A gangster who robs and kills drug dealers but never harms civilians and considers Sunday to be a day of peace to accompany an elderly woman who “is like his mother” to church.

This is just one of the many things that make Omar a fully developed character who almost feels like a sort of super hero. He was fearless and didn’t play by the same rules everyone else did. Take, for instance, the time he showed up in court to testify against one of the Barksdale crew’s members and went head-to-head with their high powered attorney.

There’s a universal code of the streets that says “snitching” in any form is the lowest and most disgraceful thing you can do. But Omar couldn’t care less because there was a means to an end with his strategy, and besides, if the most vicious killers in the city couldn’t touch him, then who would?

Omar Little faced off with the fancy lawyer of his drug-dealing enemies, and he turned the lawyer’s accusations that he “leeches off the drug trade” upside down. The lawyer couldn’t believe that Omar, rocking a tie over his regular street clothes, would give accurate testimony, considering his “profession” of robbing drug dealers. But Omar showed him who’s boss and shut him down in a hilarious way.

As the attorney went on a tirade of explaining to the jury that Omar was a “parasite who leeches off the culture of drugs,” he was cut off by Omar saying, “Just like you, man.” Without skipping a beat, Omar continued with the iconic line, “You got the briefcase, and I got the shotgun…it’s all in the game, right?”

One thing to notice was that Omar didn’t curse. In this scene, he reinforces the fact that he doesn’t hurt innocent people when the attorney accuses him of being just like the others. “Hey man, I ain’t never put my gun on no citizen,” was the only time we saw Omar lose his cool, and it was only for a few seconds.

Another memorable moment was when Omar took down a group of dealers in a classic Wild West-style street shootout and declared, “You come at the king, you best not miss.” He’s the king of the stick-up game, and he’s not afraid to show it. He’s got a swagger and a one-liner for every occasion, and this one is just too good not to repeat. This is also what makes him a strong antihero. It’s almost impossible not to root for this dude.

Omar And His Crew

Omar and his gang of outlaws are the ultimate criminal dream team—small but mighty. They’re a constantly changing group—sometimes a band of merry bandits, other times it’s just Omar and his impressive arsenal of guns. But don’t be fooled; size doesn’t matter when you’re the baddest of the bad in West Baltimore. With Omar’s leadership and his trusty gun collection, they’re a force to be reckoned with and always leave their mark on the streets.

Omar’s organization consists of roughly eight criminals in total, including himself. We’ve already talked about Omar, so let’s look at some of his associates.

Blind Butchie: The Mentor.

First up, there’s Butchie, also known as “Blind Butchie.” Butchie runs an East Side Baltimore bar and is the man Omar goes to for financial advice and support. He is essentially Omar’s bank. Butchie, like the actor who plays him, S. Robert Morgan, is actually blind. Butchie (the character) lost his sight due to a gunshot wound, while S. Robert Morgan (the actor) lost his sight due to macular degeneration.

Butchie’s bar is the spot for gangsters to hang out and chat, settle beefs, or just have neutral ground. But it’s not just a place to grab a drink; it also serves as a front for Butchie’s own drug shipments. He’s always got his finger on the pulse of the criminal underworld, and his bar is the hub of all the action.

Butchie used to be a feared enforcer in the drug game, but after losing his sight, he mostly stepped away from it. He’s like a mentor figure to Omar and his crew, always offering guidance and a listening ear.

Losing his sight doesn’t slow Butchie down one bit; in fact, it’s made him even more perceptive. He can sense when Omar is near and can always tell what kind of beer is in a crate just by feeling it. He’s a master at using his other senses to navigate the world around him.

Butchie’s loyalty is put to the test when he gets caught up in a rough situation with Chris and Snoop. They tie him up, beat him, and shoot him in the legs, trying to get him to spill the beans about Omar’s whereabouts.

Butchie doesn’t crack, and eventually, Chris gets fed up and just kills him. Chris thinks that when Omar finds out what happened, he’ll come back to Baltimore looking for revenge, and he’s right. Butchie’s loyalty to Omar runs deep, even in the face of torture.

Brandon Wright

Brandon was more than just Omar Little’s boyfriend; he was also a member of his stick-up crew. But, one day, while they were robbing a stash in the low rise projects, Brandon made a big mistake and let slip Omar’s name in front of some Barksdale drug dealers. That little slip-up started a long-running feud between Omar and the Barksdale organization.

Avon Barksdale even put bounties on all of Omar’s crew. Unfortunately for Brandon, he was spotted by Wallace and Poot Carr playing pinball at “The Greek’s” a restaurant on the west side. They told D’Angelo Barksdale, who passed the message to Stringer Bell.

Stringer and his crew, Marquis “Bird” Hilton, Roland “Wee-Bey” Brice and Anton “Stinkum” Artis, arrived and captured Brandon. They tortured and killed him, and Avon ordered that his body be displayed in the low-rise projects as a warning to Omar.

After that, Omar couldn’t let it go, and he escalated their feud, refusing to back down after the ruthless act they did to Brandon. He always referred to Brandon’s murder as being unnecessarily harsh.

It’s worth mentioning that Brandon didn’t give Omar up either when being tortured. He was just as loyal to Omar as Butchie was.

John Bailey

Bailey was part of the crew that helped Omar stick-up the Barksdale organization. But he had a lot of enemies, and it caught up with him. He was killed off-screen while visiting relatives. Rumor has it that there were 39 bullet casings found around his body, and not a single one was fired by him. Some say he was wearing a bulletproof vest, which could explain why he was shot so many times.

Omar and Brandon, despite working with him, weren’t too broken up about Bailey’s death. When Barksdale enforcer Wee-Bey Brice was arrested, he confessed to Bailey’s murder. Bailey was known for having a lot of enemies, so it was just a matter of time before something like this happened.

Kimmy and Tosha

Kimmy and Tosha Mitchell were a couple who made a living by robbing drug dealers. When Omar came back to Baltimore, he convinced them to join his crew. Kimmy was a pro at infiltrating drug dealing operations, using a bunch of different disguises, including a nurse and a disabled veteran.

Things got a little tense between the trio when Dante, another member of the crew, started feeling jealous of their relationship with Omar. Things got worse when Dante accidentally shot Tosha during a failed raid. Kimmy blamed Omar for putting them in that dangerous situation and decided to leave the crew. But, eventually, she forgave him and came back to help him steal a huge drug shipment from Proposition Joe’s co-op.

But as Omar’s vendetta against the Barksdale organization continued, Kimmy decided that there were easier people to rob and left the crew. After successfully stealing Proposition Joe’s drugs, Kimmy took her share and told Omar that she was retiring from the life of crime.

Dante

Dante becomes Omar’s next boyfriend after Brandon. They start dating sometime in the year after Brandon’s murder, and he joins Omar’s stick-up crew. But things get a little tricky when Dante starts getting jealous of Omar’s other associates. This jealousy leads to a rift between him and the rest of the crew, which gets worse when he accidentally shoots Tosha during a failed raid.

Things don’t get any better for Dante in season three, when he gets kidnapped and beaten. In a moment of weakness, he sells Omar out to Brother Mouzone. It’s pretty clear that this is the reason why he and Omar split ways, as he hasn’t been seen again since then.

Renaldo

After Dante, Omar gets a new partner in crime, and this time it’s Renaldo! He’s the first major Hispanic character on the show and brings some fresh blood to Omar’s stick-up crew. He’s new to the game and still getting used to all the reconnaissance that goes into robbing drug dealers.

But he’s got a secret weapon; he’s not as well known to the drug dealers as Omar, so he can sneak around and gather all sorts of juicy intel. Plus, he’s got a sweet ride in the form of his own taxi, which they use for all sorts of sneaky surveillance missions.

Once they hit the big score by stealing Proposition Joe’s shipment, Renaldo and Omar decide to retire in Puerto Rico and live the good life. But while Omar goes back to Baltimore after hearing the news of Blind Butchie’s death, Renaldo chooses to stay in retirement and enjoy the fruits of their labor. He’s not one to look back, only forward, to the next adventure that might come his way.

Big Guy and Donnie

Big Guy and Donnie are Butchie’s trusty sidekicks, who work at his bar and act as his personal muscle. When Omar gets arrested, Butchie sends these two big guns to protect him, and they both willingly get thrown in jail just to make sure Omar stays safe. Talk about loyalty.

Their help comes in handy when another prisoner tries to kill Omar.

Big Guy is hanging out at the bar when Chris Partlow and Snoop ambush Butchie, and he gets shot in the leg. The Stanfield enforcers kill Butchie, and Big Guy is left alive as a witness. He tells his story to Omar, and that’s what prompts him to come out of retirement to get revenge for Butchie.

Later, Donnie gets out of prison and joins Omar in his quest for revenge for Butchie’s death. But unfortunately, he gets caught in an ambush that the Stanfield gang sets for him and Omar, and he meets his end. But he goes down in a blaze of glory.

Rest In Peace Michael K. Williams

Fans paid their respects to the late actor Michael K. Williams on social media when he passed away. He was best known for playing the role of Omar in “The Wire,” but he also made a name for himself as a menacing mob boss on “Boardwalk Empire” as a character named “Chalky White” as well as playing a captivating alcoholic father on “Lovecraft Country.”

The 54-year-old star, who was found dead in an apparent overdose in his Brooklyn penthouse, once told Vanity Fair he picked roles that told the stories of black men with nuance and honesty. He told the magazine, “I don’t get to assimilate into anything other than the black experience.”

He also said, “For me to be given the opportunity to be a storyteller and to tell a narrative of people in my community that look like me, I wear that as a badge of honor — and a huge responsibility.”

“I’m grateful for the gift of art—if nothing else, just for that.”