At Adair, Iowa, Jesse James and the James–Younger Gang pull off the first successful train robbery in the American Old West.

Adair is a city in Adair and Guthrie counties of Iowa in the United States. The population was 791 at the 2020 census.

Jesse Woodson James was an American outlaw, bank and train robber, guerrilla and leader of the James–Younger Gang. Raised in the "Little Dixie" area of Missouri, James and his family maintained strong Southern sympathies. He and his brother Frank James joined pro-Confederate guerrillas known as "bushwhackers" operating in Missouri and Kansas during the American Civil War. As followers of William Quantrill and "Bloody Bill" Anderson, they were accused of committing atrocities against Union soldiers and civilian abolitionists, including the Centralia Massacre in 1864.

The James–Younger Gang was a notable 19th-century gang of American outlaws that revolved around Jesse James and his brother Frank James. The gang was based in the state of Missouri, the home of most of the members.

Since the invention of locomotives in the early 19th century, trains have often been the target of robbery, in which the goal is to steal money or other valuables. Train robbery was especially common during the 19th century and is commonly associated with gangs of outlaws in the American Old West. It has continued into the 21st century, with criminals usually targeting freight trains carrying commercial cargo, or targeting passengers of public transportation for their valuables.

The American frontier, also known as the Old West, and popularly known as the Wild West, encompasses the geography, history, folklore, and culture associated with the forward wave of American expansion in mainland North America that began with European colonial settlements in the early 17th century and ended with the admission of the last few contiguous western territories as states in 1912. This era of massive migration and settlement was particularly encouraged by President Thomas Jefferson following the Louisiana Purchase, giving rise to the expansionist attitude known as "manifest destiny" and historians' "Frontier Thesis". The legends, historical events and folklore of the American frontier, known as the frontier myth, have embedded themselves into United States culture so much so that the Old West, and the Western genre of media specifically, has become one of the defining features of American national identity.