The year is 1899. The era of the Wild West is beginning to come to an end as the federal government asserts its control over the lawless territories. Realizing their fortunes are fading, the notorious Van der Linde gang led by Dutch plots one last major bank robbery that could set them for life. However, the heist goes awry with several gang members dead or captured; the gang is forced to flee across the country with the law pursuing them. Undeterred, Dutch hopes to pull off one last heist and flee the country. However, each scheme ends in failure in one way or another. Dutch's most trusted lieutenant, Arthur Morgan, sees his loyalty to the gang put to the test as he is forced to come to terms with the changing times.