Back in its heyday, series depicted life in Baltimore from the street corner all the way to the mayor's office, unflinchingly giving a portrayal of the city's crime, corruption, and the violence surrounding a morally ambiguous drug war.
Aside from cops, many of the main characters were of different gangs within the city. Some of these gang leaders were fierce and ruthless, while others were more subdued, but all felt like real people. In fact, many were even based on real-life Baltimore-based criminals. Here is every gang leader on The Wire, ranked in order of how intimidating they were:
The Greek
The second season took a surprising new direction as it moved away from the street corners to focus on crime at the docks, examining the connection between the stevedore's union and Eastern European organized crime. The Eastern European mobsters were ruthless, trafficking in both women and drugs. They killed without mercy or hesitation. Their leader, a tiny old man named the Greek, was even crueler than most of his soldiers.
However, he was a soft-spoken and seldom got his hands dirty, spending much of the series sitting in the corner of a small diner. Someone so quiet and demure never managed to come across as intimidating -- especially when contrasted with those under his command.
Prop Joe
Prop Joe was the most powerful gang leader in East Side Baltimore. A large man with short locks, he was always willing to make a proposition, often setting aside the code of the streets for a brief moment to talk business.
Despite his seemingly mercenary attitude, Prop Joe was a diplomat. While he might stray from the honor codes of Baltimore gang life every now and then, he often demonstrated a comionate side few of his fellows seemed to share. He bore responsibility for a number of deaths, but despite this, he came across as a decent guy.
Clay Davis
Being a politician, Clay Davis might not have been a gang leader in the traditional sense, but he had ties to multiple gangs and on at least two occasions he was seen profiting directly from the Barksdale Crew's West Side drug monopoly. Clay was not a part of the Barksdale Crew, as he tried to scam Stringer Bell, and for the purposes of this list, his political status should be considered its own gang of sorts.
He was a slimy bureaucrat who lined his pockets with cash gained from criminal enterprises, having no respect whatsoever for the people he represented. He could be all charm and smiles one moment, then enter a furious rage the next, but what made him so intimidating was that he was usually still smiling when he stuck the metaphorical dagger in someone's back. Not helping his case is his hilariously unforgettable delivery of a certain curse word that rhymes with "hit."
Stan Valchek
One point The Wire emphasized was that there was little difference between the violence and corruption of Baltimore Police and the street gangs. This is a disturbing parallel that the show's creator David Simon witnessed firsthand while working as a journalist in the city. On that note, Stan Valchek was Commissioner of the Baltimore Police Department, but he did not care about solving cases or reducing crime. Rather, he was obsessed with petty interpersonal vendettas, driven by all-consuming jealousy and spite.
Valchek formed an entire task force to harass the stevedore's union just because the head of the union made a more generous donation to Valchek's church. He lashed out at family and coworkers alike. These sorts of thuggish behaviors were downright bestial compared to the more tempered responses of Baltimore's street gangs, who at least lived by a code. Valchek's only code was to serve himself.
Stringer Bell
As one of the two leaders of the Barksdale Crew, Stringer was the respectable face of operations. He took business classes at the local community college and was dedicated to gaining legitimacy as much as making a profit. While Stringer was removed from the street operations, he was not above getting his hands dirty. He even had Avon's nephew, D'Angelo, killed in prison, despite D'Angelo taking the fall for his crew's crimes.
Stringer was suave and sophisticated, but he was ruthless when anyone got in his way. He eventually set up his best friend, Avon, to get nailed by the police.
Avon Barksdale
Avon was the main leader of the Barksdale Crew, lending it his last name. He ran a smart operation, taking over the West Side and dominating the drug trade while dropping bodies left and right. He had a connection to heroin coming in from New York and plenty of soldiers whose muscle helped to guard his product.
At the end of the first season, he was locked up by the Baltimore Police. When he got out, the game on the streets had changed and he had a hard time adapting. He eventually gave up his best friend, Stringer Bell, to be killed by Brother Mouzone, a soldier connected to the New York heroin trade. Stringer had betrayed both Avon and Brother Mouzone for profit, but Avon prioritized his family and honor above all else -- two things Stringer had compromised.
Omar Little
Omar ran a small crew, but as an openly gay gangbanger who stuck up drug dealers, he was an absolute legend on the streets. His grandmother raised him on Greek myths and he lived like a modern-day Greek hero, wielding his shotgun and whistling in the streets as he warred against his enemies with the fury of Achilles.
He was probably the most honorable and honest character in the series. He's so virtuous that he was notably the only major character who didn't curse in a show known for its crass street dialogue. Despite that, no one wanted to be on the wrong side of Omar, and those who earned his ire paid for the mistake in blood.
Marlo Stanfield
After the decline of the Barksdale Crew, a new gang rose to power under the leadership of Marlo Stanfield. While there was no shortage of killers in the series, Marlo was a genuine sociopath, respecting neither honor nor tradition in his unbridled cruelty. The only things he valued were his reputation and power.
In his very last scene in the final season, Marlo wore a suit in the streets and approached a group of bangers on the corner who were talking about Omar. The corner crew failed to recognize Marlo and one of them drew a gun on him. He disarmed the gunman with ease, but the man still got a shot off, grazing Marlo and ruining his suit. The truth of the matter was that Marlo could never escape the street, and his ion for unbridled violence tore through any attempt at respectability he might pursue.