Bosses rule the underworld of Maretropolis, each maintaining a formidable grip on their respective gangs and markets. Some bosses are at odds with each other, but almost all of them are categorically opposed to law enforcement, including the Justice League of Equestria, which stands against their illicit operations.
- See also: Bayne
Bayne is a master mercenary and a fearsome hulk of a criminal who maintains a small ring of elite killers. Bayne's ring, including Bayne himself, is usually found in employment to one of the other bosses, who pay a hefty fee for their expertise and brutality. Neighson Wynn in particular has a history of dealings with Bayne's menaces-for-hire.
Mr. Cobbletrot is an arms dealer and contraband fencer who fashions himself a gentlecolt and operates from his nightspot, the Iceberg Lounge. Cobbletrot specializes in arming super-villains and the like, though he is also willing to deal with super-heroes such as Goldfin whenever they "visit" for information. Although he has his differences with several powerful families, Cobbletrot's name is a mighty one in both the squalid streets and the cushy offices of Maretropolis.
- See also: Captain Death-Stalker
The wicked captain of the Death's-Head runs a small empire of his own with the Unholy Three as his elite agents. His gang specializes in technology piracy and robbery, but it remains willing to step into any field to net a profit. Since the rebellion of Acolyte 2.0 and the theft of the Maretropolis Science Center's graviton generator, it has also become the fastest-growing gang on the east coast.
Carmine Falconeigh, sometimes called the Roman, is one of the strongest crime lords in Maretropolis for the simple reason that the courts are on his payroll. Falconeigh is allegedly superstitious and paranoid, but his anxiety seems to be reaching new heights. Recently and to the bewilderment of the other bosses, he put a price of seventeen million bits on the Crimson Cowl's head. However, this proved to be the work of Doctor Mid-Nite, who had captured the Falconeigh family at Baltimare and taken the don's place with the aid of some makeup and a wig.
Carmine Falconeigh has recently become yet another one of Bloodstorm's victims.
The Mane-iac ran a sizable gang of anarchists and lunatics, though even they found it difficult to keep up with her antics. They spent most of their time protecting the Ace Cosmetics Plant and performing tasks too menial for the super-villainess. Once Captain Orbit had the Mane-iac restored to her former self, this gang went defunct for a time.
Doctor Mid-Nite revived the old gang for his takeover of Carmine Falconeigh's syndicate. He and Jane Neighpier, now calling themselves Mr. and Mrs. Mane-iac, offed Carmine's sons during their stay in Baltimare and abducted the old stallion, allowing them to usurp his entire operation unimpeded. Disguised as Falconeigh, Mid-Nite reaped the crime family's bountiful life insurance and transferred the gang's funds to Jane's old accounts, effectively absorbing the Falconeigh gang into the Mane-iacs' own. Since then, the Mane-iacs have been "back in business" with the intention of making mischief and repaying the Power Ponies for Jane's redemption.
Sal Mareoni is arguably the most powerful and the most ruthless of the crime lords in Maretropolis. Mareoni specializes in smuggling and extortion, though he is not above graver iniquities if it means snuffing out competitors, and he is no stranger to such evils. Mareoni's goons include Rico Stride, perhaps the most vicious rake roaming the streets, and even a few minotaurs. Mareoni's forces often strike with little warning and little mercy, relenting only if the boss's demands are met. Jane Neighpier and Warden Steely Gaze are known targets of Sal Mareoni.
Silvermane is one of the oldest crime lords. Unlike most crime lords, he doesn't mind the Justice League of Equestria too much and even sees them as helpful at times. However, anyone who's an obstacle to him will quickly feel his wrath. Silvermane excels at cybernetics and has created some of the most advanced cybernetic exoskeletons Equestria has ever seen. This is all a part of his personal quest to gain immortality.
Tony Twist is Equestria's Nr. 1 black market dealer. If someone wants an illegal item, either for themselves or to send elsewhere, Tony Twist is their go-to pony. Smart and cunning, but not very brave, Tony Twist prefers to let his hired guns to the dirty job for him.
He answers directly to Neighson Wynn.
- See also: Neighson Wynn
Neighson Wynn is perhaps the only crime boss who could give even Sal Mareoni a run for his bits. He has ties to both the Equestrian goverment and the underground black market with both politicans and other crime lords under his payroll, effectively making him one of Equestria's most powerful individuals. He is utterly ruthless and will not hesitate to kill anyone who is a liability or an obstacle to him. He's a very elusive crime lord, as few people know of his criminal ties and those who tries to reveal them are usually reminded of their debt to him, killed without anyone noticing or simply proven wrong in court.