Robinson's early struggles led many of his poems to have a dark pessimism and his stories to deal with "an American dream gone awry." His eldest brother, Dean Robinson, was a doctor and had become addicted to laudanum while medicating himself for neuralgia. The middle brother, Herman, a handsome and charismatic man, married the woman Edwin loved, Emma Löehen Shepherd. Emma thought highly of Edwin and encouraged his poetry, but he was deemed too young to be in realistic competition for her hand, which didn't keep him from being rattled deeply by witnessing what he considered her being bamboozled by Herman's charm and choosing shallowness over depth. The marriage was a great blow to Edwin's pride, and during the wedding ceremony, February 12, 1890, the despondent poet stayed home and wrote a poem of protest, "Cortège", the title of which refers to the train that took the newly married couple out of town to their new life in St. Louis, Missouri. Herman Robinson suffered business failures, and also started working life as an alcoholic, and ended up estranged from his wife and children. Herman died impoverished in 1909 of tuberculosis at Boston City Hospital. Robinson's poem "Richard Cory" was thought by Emma (Herman's wife) to refer to her husband.