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Rufus and Wyatt track Flynn and his captive Lucy to the 1893 Chicago World Fair. However, Flynn, anticipating their arrivals, sends them to the World's Fair Hotel: the "Murder Hotel" of serial killer H.H. Holmes.
The team trace Flynn to 1780 and discover that he plans to use Benedict Arnold to get to Rittenhouse... and kill him. Now the trio must decide whether they will help Flynn or hinder him.
Flynn travels to 1882 to save Jesse James and hire him to lead him to a remote cabin. The team follows him to 1882 and team up with Marshal Bass Reeves and his friend Grant to track Flynn and Jesse down. Meanwhile, Connor begins training Jiya so that she can replace Rufus.
When an experimental time machine is stolen, a history professor, a soldier and an engineer are tasked with capturing the culprit. They soon learn that the thief plans to rewrite American history, and that each of them has a connection to his plan as well as the mysterious organization that funded the machine's development.