Pokagon was the author of several books and multiple shorter works, and is identified as part of the Native American renaissance. Some have argued that his writings may have been substantially edited by the wife of his personal attorney although that remains speculation and a matter of controversy. He claimed attendance at Notre Dame University and Oberlin College, but that has been challenged as they have no record of his matriculation. Some have challenged his claims of fluency in four of the "classic" European languages. However, others have cited his personal correspondence as clear evidence of his literacy and writing skills.
Simon was also a featured speaker at the 1893 World's Columbian Exposition in Chicago. While his popularity with some fellow tribal members waned, he was always welcomed among the Gold Coast “High Society” of Chicago and the Chautauqua literary groups from the East Coast. He was an early activist for the payment of monies owed pursuant to treaties and the fair treatment of Indian peoples.
In the 1890s, Simon Pokagon began pressing land claims to the Chicago lakefront. A complicated individual with what often seemed to be contradictory motivations, he sold “interests” in that Chicago land claim to real estate speculators, angering some in the Pokagon community.
In much of writings, Simon wrote nostalgically of the past and lamented the passing of a “vanishing” race of Indians. But the Pokagon Potawatomi were not vanishing. In fact, the Potawatomi had organized a Business Committee, a traditional, democratically elected tribal council that governed by consensus and advocated for the rights of tribal members. Meanwhile, most tribal members worked as laborers at local factories and farms and retained close ties to the Catholic Church. According to historian Susan Sleeper-Smith, unlike the neighboring Miami Indians in Indiana who "hid in plain sight” the Pokagon Potawatomi tightly held onto their traditions and sense of community.
In a publication originally titled "Red Man's Rebuke" and subsequently "Red Man's Greeting," Simon wrote in harsh terms:
On behalf of my people, the American Indians, I hereby declare to you, the pale-faced race that has usurped our lands and homes, that we have no spirit to celebrate with you the great Columbian Fair now being held in this Chicago city, the wonder of the world. No; sooner would we hold the high joy day over the graves of our departed than to celebrate our own funeral, the discovery of America. And while...your hearts in admiration rejoice over the beauty and grandeur of this young republic and you say, 'behold the wonders wrought by our children in this foreign land,' do not forget that this success has been at the sacrifice of our homes and a once happy race.
While these words place him in the context as a great early spokesperson of resistance for American Indian peoples, his speech at the World's Columbian Exposition on "Chicago Day" was reported in the October 10, 1893 edition of the
Chicago Daily Tribune as having a much more conciliatory tone:
I shall cherish as long as I live the cheering words that have been spoken to me here by the ladies, friends of my race; it has strengthened and encouraged me; I have greater faith in the success of the remaining few of my people than ever before. I now realize the hand of the Great Spirit is open in our behalf; already he has thrown his great search light upon the vault of heaven, and Christian men and women are reading there in characters of fire well understood; ‘The red man is your brother, and God is the father of all.'
Simon was not the last chief of the Potawatomi or even a hereditary chief of the Potawatomi. The Pokagons have had chiefs since his passing and leadership in Potawatomi communities is not hereditary. For a while, he was the head of the Business Committee of the Pokagon Band of Potawatomi Indians until his political fortunes soured and he was replaced. Nonetheless, to readers of American Indian literature and to tribal members alike, he remains an ambivalent icon of an early Indian who obtained "celebrity" status.
A monument to both Simon and his father in Chicago's Jackson Park was proposed but never built. (Jackson Park Office, Chicago Park District). Pokagon State Park in northern Indiana is also named for both of them.
