Agent Milton
Milton is a high-ranked detective in the Pinkerton National Detective Agency. After Dutch robs his train, Leviticus Cornwall hires Milton and his protégé, Agent Ross, to track down the Van der Linde gang and bring Dutch van der Linde to justice.
Edgar Ross
Born in 1861, Ross has a long-running career in law enforcement. He has many years of experience as a senior agent of the Pinkerton National Detective Agency, under the mentorship of agent Andrew Milton. Ross is praised as proficient and formidable in his work.
Leviticus Cornwall
Leviticus Cornwall is a wealthy man who owns many of the businesses the Van der Linde gang have their sights set on, with his greatest power accumulated in Saint Denis. He is also a financial backer of the Pinkerton National Detective Agency. After the gang robs one of his trains, he becomes determined to kill Dutch Van Der Linde
Colm O'Driscoll
Former friend of outlaw Dutch van der Linde turned rival, he is the leader of the O'Driscoll Boy's Gang. He is a ruthless and violent man who will do anything to gain power and control.
Micah Bell
Sometime after returning from Guarma, Micah begins secretly working as a rat for Andrew Milton and the Pinkerton Detective Agency, which (coupled with Dutch's own instability) causes the Van der Linde gang to fall apart.
Catherine Braithwaite
After having the gang run multiple jobs for her, she ends up double-crossing Dutch and kidnaps John Marston's four year old Jack before selling him to Saint-Denis crime boss Angelo Bronte. In retaliation, Dutch and his gang raid her mansion, killing both of Catherine's sons as well as the rest of her bodyguards and setting her mansion on fire, before Catherine revealed Jack's location.
Angelo Bronte
A crime boss who makes his money extorting local businesses, Angelo Bronte is a wealthy Italian crimelord who has a large influence in Saint Denis. Bronte's riches has allowed him to bribe every major official in the city, including the mayor. He is a powerful man who is not afraid to use his wealth and influence to get what he wants.
Alberto Fussar
Colonel Alberto Fussar is the Governor of the Caribbean island of Guarma, and owner of a large sugar plantation. Fussar eventually discovers the gang's true identity and learns that they have a large bounty on their heads. He alerts the Cuban Navy and sets up gun batteries on the shore to stop them from leaving.