The story of the Great Southwest strike, a textbook example of the upheavals of 1886, has long been told as an epic battle between railway millionaire Jay Gould, national Knights of Labor head Terence Powderly, and Martin Irons, with many historians and contemporaries casting strike leader Irons as the epitome of impatient, romantic, and even deluded labor activism. District Assembly 101's call to walk out on Gould's southwestern system of roads was, arguably, strategically ill-advised. It vastly overestimated the Knights' power in the wake of two victories against Gould in 1885 and certainly ignored the district's lack of funds, lax support among skilled trainmen, and the terms of an historic agreement between the national Knights and Gould. A closer look at Irons's life and leadership, however, reveals a more complicated explanation of the strike and takes into fuller account the experiences and perceptions of striking railroaders. This essay holds that events on the ground, combined with the heady context of the Great Upheaval, influenced Irons and his supporters' decisions to strike, to expand the effort, and to defend it with violence. The ensuing attacks on Irons stemmed partly from his unstable personal history but largely from the broader social anxieties that the conflict had exposed.