This article explores blacklisting practices following the massive 1886 Southwest strike staged by the Knights of Labor (KOL) against Jay Gould's railroad empire. It focuses mostly on strike leader Martin Irons and blacklisting advocate and newspaperman J. West Goodwin. The strike, which started in Sedalia, Missouri, before spreading to other states, was a disaster for the KOL. The union declined in its aftermath chiefly because of the repression unleashed by public and private forces, including businessmen-led Law and Order Leagues. After the strike, employers blacklisted many, including strike leader and Sedalia resident Martin Irons. Irons, constantly on the move, suffered from joblessness, underemployment, arrests, and broken health before he died in central Texas in 1900. Few blacklisting advocates wanted Irons to suffer more than J. West Goodwin. The Law and Order League leader and newspaperman repeatedly wrote about what he considered Martin Irons's moral lapses and shortsightedness. By focusing on Goodwin's promotion of blacklisting and Irons's post-strike struggles, this essay helps us better appreciate the underexplored dimensions of this form of punishment.