At some point prior to 1899, Ike Skelding established his own gang of bounty hunters, eventually becoming one of the most notorious bounty hunters in the area circa 1897. 
Events of Red Dead Redemption 2
Ike Skelding's men manage to capture the outlaw and Van der Linde gang member Sean MacGuire shortly after the Blackwater Massacre. However, instead of turning him over to the law immediately, Skelding and his men decide to head west to take Sean to a federal prison. On the way, his men are intercepted by Arthur Morgan, Charles Smith and Javier Escuella, fellow members of the Van der Linde gang, who manage to gun down Skelding's men and save Sean.
It is unknown whether or not Ike Skelding himself was among the dead, although newspapers do not seem to report activities of his group after this.
- Red Dead Redemption 2
- "The First Shall Be Last" (mentioned "possibly" present during the assault)