Monty the Decker








Sinister Three (Associate)


Second-in-command at the Deckers


Mr. Sinister (older brother)
Jessica (wife)

Montgomery is the younger brother of Mr. Sinister and a member of the Deckers. He is a contact in The Sinister Three.



Montgomery and his older brother Mr. Sinister began working together as gun-for-hire for many mob families in their hometown. Mr. Sinister at the time was working as an enforcer in a rising mob family, and brought Monty in to help assist. Both of them took on hit jobs and made plenty of money. However Monty found himself backing out of the life when his house was burned down by a rival gang, and he left the city with his wife.

Monty later began hacking and doing his crimes over the net, which brought him to the attention of Matt Miller - the leader of the Deckers in Steelport. Matt was close to securing a position working for the Syndicate and got in contact with Monty to act as his right hand man.

Monty went underground when Matt had left Steelport and the Syndicate were dissolved.

The Sinister Three

With little money leftover, Monty went through divorce problems with his wife Jessica. He contacted his brother's gang the Sinister Three to kidnap her, saving him money on court proceedings.

Third Street Girls

When Mr. Sinister is confronted by Shaundi, Viola and Cypher, they begin to mention the contacts closely working with Mr. Sinister and his sex ring and how they picked them off. Monty's wife Jessica states that they have dealt with Monty, however refuses to answer Mr. Sinister's question whether or not they killed or spared his life.


Montgomery is an intelligent and rather ambitious individual. Inspired by his older brother's crimes and plans to rise in power, Monty jumped on board to make a name for himself. However Monty had proved to be less than useful on the field when dirty work needed done, and was scared off when he found himself nearly killed by gang members. Monty instead took to hacking online, enjoying feeling anonymous.

Like his brother Monty appears to have quite a cold personality, and was willing for his wife to be kidnapped rather than help pay for the court proceedings of their separation. He also seemed to be jealous of her new partner, and pardoned the Sinister Three to kill him during the abduction, showing he disregards another's life and doesn't have much empathy.