In 1899, The whole Gang of Dutch Van Der Linde was on a journey to Blackwater because of a rivalry with another gang named O'Driscoll. On their Journey to Blackwater a ferry was carrying $150,000 of bank money. Dutch van der Linde saw an opportunity and decided to rob the boat. He was also encouraged to pursue it by Micah Bell. Despite the absence of two senior members of the gang, Arthur Morgan and Hosea Matthews, who had their own lead, the remainder of the outlaw gang proceeded with the robbery. According to Javier Escuella, the heist got off to a good start, with the gang accessing the money fairly easily. However, Pinkertons soon swarmed the area, along with the police, forcing the outlaws into an unwinnable gunfight. While the following events are somewhat ambiguous and never made clear, it is known that at some point during the heist, Dutch shot a young woman in the head.
The gunfight proved to be devastating for the Van der Linde gang. The gang could not escape with the stolen money and instead stashed it in an undisclosed location in the town known only to Dutch and Hosea. After regrouping, the gang began packing up and then headed north into a blizzard in the mountains of Ambarino, successfully losing their pursuers in the process.
