Statue of “Toto the Windsor Indian” in Forest Park in Springfield, MA, 2019. WHS collections 2019.42.2, photo by Michelle Tom.
Although memorials are designed to commemorate and honor past people and events, the unceasing march of time has the tendency to replace remembering with forgetting. Just over the Connecticut border into Massachusetts, the town of Longmeadow and the neighboring city of Springfield is peppered with such forgotten mnemonics. One might stand at the spot where Metacomet Road intersects with King Philip Drive and be unaware of the fact that these two residential streets are both named for the same man, the feared leader of “the Native Americans’ last-ditch effort to avoid recognizing English authority and stop English settlement on their native lands”. The beauty of Turner’s Falls obscures the fact that 200 men, women, and children, members of the Narraganset tribe, were shot or plunged to their deaths as they retreated from English soldiers.
The area in Forest Park known as King Philip’s Stockade has become a popular place to host a summer party, and visitors might stop to look at the bronze statue of an unmarked Native American behind an iron fence enclosure. While there is no nearby sign indicating who this man is, or even whether he depicts a specific person, scholars of Springfield or Windsor history will know him as “Toto the Windsor Indian.” In the case of Toto, he isn’t exactly forgotten. His story is told in countless accounts of the Siege of Springfield during King Philip’s War.
According to legend, on October 4, 1675, Toto learned of a surprise attack on the city of Springfield being planned by King Philip’s soldiers. In response to hearing this news, Toto ran 20 miles from Windsor to Springfield to sound the alarm. Toto is credited with saving the people of Springfield from a massacre. But the legend conjures up several questions for the historical record: How did Toto find out about the conspiracy? Who were his confidants? What compelled him to betray them? Did he really run 20 miles in a single night?
Henry Morris’ Early History of Springfield 1636-1675, which is widely cited and quoted throughout the various accounts of the incident, describes Toto as a “friendly Indian” who was “domesticated in the family of” Henry Wolcott Jr. Per Morris’ account, Toto appeared so visibly distraught that the family extracted the story from him. This information leads to yet another question: how did Toto end up with the Wolcotts?
We know from land records that Toto was the grandson of Nassahegan, the last Poquonock sachem in the Windsor area. Sachems essentially functioned as monarchs within their domains and, with the input of council, controlled both the land and the people. That Toto had experienced such a reduction in status—from sachem’s heir to domestic servant to the English—is jarring. Obviously the influx of the British sociopolitical system had radically altered the Poquonock way of life and means of survival, but records show that Toto was still selling land well into the 1680s, so although he wasn’t a sachem, he still maintained some form of control over his grandfather’s former domain.
Montage of Toto’s signature mark from various land deeds. Note that these versions are interpretations of Toto’s mark, as drawn by town clerks for the official town copies of the land deeds. Toto’s original mark, drawn in his own hand, would have been on the land deed copies that were given to the parties involved in the land transaction. Courtesy of the Towns of Windsor, CT and Granville, MA Town Clerk’s Offices.
By combining a more general account of how Native Americans were often enslaved by white settlers with what we know about Henry Wolcott Jr., it might be possible to speculate on Toto’s presence in the Wolcott household.
In Brethren by Nature: New England Indians, Colonists, and the Origins of American Slavery, Margaret Ellen Newell offers a critical unearthing of Indian servitude and slavery in New England, which has largely been obscured from the historical record. Newell explains:
Throughout New England before 1700, and in subregions thereafter, Native Americans represented the dominant form of nonwhite labor. They toiled in ironworks, fisheries, livestock raising, extensive agriculture, provincial armies, and other enterprises that required unusually large work forces.
This labor was secured in many ways—through paid wages, indentured servitude, and outright slavery. By “purchasing” lands, introducing new consumer goods to the area, and dictating social “norms,” the white settlers brought a new socioeconomic system into the greater New England area, and this system ensnared many of the region’s original inhabitants.
As a result of increasingly complex legal codes that “undermined essential Indian economic activities,” especially those relating to the leasing of land, “the Indians slowly become proletarianized”. The burgeoning New England governments continued to write laws and codes that restricted the activities of Indians and fined them for infractions. When these fines evolved into unpaid debt, conditions of servitude were imposed, and, according to this system, the enslaved workers were no longer able to reap the benefits of one of the only appreciable assets the new system left them with: their labor.
One of Windsor’s earliest settlers and a prominent local merchant, Henry Wolcott Jr. possessed an abundance of land and was involved in many enterprises, some of which likely would have relied upon Indian labor. In 1671, four years before the Toto legend in question, he boasted that he “made 500 hogsheads of Syder out of his own orchard in one year”. By the time of his death in 1680, he “owned some 34 acres of orchards in Windsor”. He would have needed laborers to work in his orchard, as well as to perform other duties throughout his properties. Wolcott has the regrettable distinction of being the first person on record in Windsor to own a “Negroe” enslaved person,  so it stands to reason that his moral code would have allowed for the exploitation of all groups he considered to be subaltern, including Indians. Toto’s apparent freedom later in life (when he was selling land) indicates that he was not permanently enslaved within the Wolcott household. However, in Newell’s words, “chattel slavery and freedom were at opposite ends of a broad spectrum, and many Indians occupied points along that spectrum in varying degrees of unfreedom”.
So although a documentary record explaining Toto’s presence in the Wolcott’s household has not been found, contextual evidence suggests that he was a laborer of some kind.
Further, Henry Morris’ assertion that he was “domesticated” into the household is suggestive of a long-term relationship between Toto and the Wolcott family. If Toto was an indentured servant, the imposing of this status could have been the result of either crime or debt, and laws surrounding Indians and alcohol often got individuals tangled up in both of these circumstances. While there is no court record of Toto drinking or being tried for such, it was not uncommon for white settlers to provide Indians with alcohol as a form of entrapment specifically for the purposes of extorting money or land from them. We do know that Sepanquet, an uncle of Toto’s, deeded land to Samuel Marshall in exchange for Marshall paying a fine (a “consideration of a sum of money”) on Sepanquet’s behalf to the County of Hartford, and so there is a precedent within Toto’s family line of falling into such a predicament.
It’s also completely possible that Toto was employed by the Wolcott family for fair wages and of his own accord. Although most Indians who worked for wages did so by the day or seasonally, a more long-term form of employment may have actually come about because of Toto’s relatively high status as grandson of a previous sachem. According to Newell,
“From the Indians’ perspective, sometimes service in New England homes created avenues for power within their own indigenous communities, or led to profitable roles mediating relations between English and Indians in this increasingly hybrid society”.
By becoming a trusted member of the Wolcott household, in whatever form that may have taken, Toto would have been able to learn any number of skills necessary to successfully navigate English culture, economy, and bureaucracy.
Despite the several possible explanations for why Toto would have been working for the Wolcott family, we still don’t have a clear explanation as to how or why he would have learned about the planned attack on Springfield. However, one potential answer, albeit one that cites no sources, comes from a Springfield history book written for children. Author Charles Henry Barrows speculates that Toto was informed of the impending attack by a group of Agawam Indians who were traveling to Hartford on October 4, 1675 in order to retrieve a group of hostages that they had given to the English settlers as a show of good faith between the Agawam tribe and the English. As Barrows notes, if this group of hostages hadn’t been handed over, and the siege of Springfield was carried out, the English would have murdered them in retaliation. If, in 1675, you were travelling to Hartford through Windsor, you wouldn’t have been able to do so without passing by Henry Wolcott’s land, and possibly even his apple orchard.
Map of Windsor circa 1633-1650, highlighting land belonging to Henry Wolcott Jr. (and Sr.). This does not show the entirety of his land holdings, as he also owned property on the east side of the river. The highway from Springfield to Hartford is colored yellow. Courtesy of the Memorial History of Hartford County, as published in Henry Stiles’ History of Ancient Windsor. Edits by Michelle Tom.
We can now connect the dots to suggest that Toto, while working in Wolcott’s orchard—apple harvesting is at its peak between September 1st and October 25th—might have spoken with the delegation of Agawam Indians as they made their way to Hartford. We can imagine a scenario in which young men, tasked with rescuing vulnerable hostages, would have stopped along the way and boasted about the upcoming attack. We don’t know enough about Toto as an individual to know why he would have betrayed this confidence, but we can’t assume that he, a Poquonock from Connecticut, had any particular allegiance to a group of Agawams from Massachusetts. If Toto was working for the Wolcott family in order to increase his own standing and influence in the new social order, then perhaps it would have been beneficial for him to be perceived as a loyal informant. Or perhaps he was simply compelled by his own moral code.
Lacking any specific accounts of Toto’s motives, explanations for his actions are limited to contextual guesswork.
All of this is to say that by scouring the historical record, we can locate a plausible explanation for how, where, and why Toto would have heard about the planned attack on Springfield. We can also draw conclusions about why he might have been in Wolcott’s household and speculate that Toto’s relationship to the family was more complex than the benevolent, patriarchal portrait of loyalty that Henry Morris alleges. We cannot, however, substantially prove or disprove his running 20 miles in the course of a single evening, though for a very fit runner it would be physically possible at least. Barrows attributes this journey to a “swift [English] messenger,” which greatly reduces the mythical nature of Toto’s narrative.
Toto, peering in the direction of Windsor, and his unmarked surroundings in King Philip’s Stockade, 2019. WHS collections 2019.42.1, photo by Michelle Tom.
The legend of Toto invites interrogation into the motives of memory. If King Philip’s War was the “bloodiest war per capita” in American history, then why did the victors, the white settlers, need to remember the legend of Toto? Did the notion of a friendly Indian, running through the night to save the women and children of Springfield, tromp down some of the animosity and fear that followed the war? Would the “swift messenger” described by Barrows not have the same romantic cachet as the loyal and fast Toto? Was Toto’s story a way of domesticating the brutality of history—hundreds of deaths obscured by the tale of one hero? Was it a kind of warning shot, sent out to defeated tribes? By creating a false binary, the friendly Indian versus the unfriendly Indian, were the English setters issuing a tacit ultimatum to Native American survivors of King Philip’s War?
Whatever the answer, Toto’s statue isn’t telling many tales. Instead, it serves as a physical reminder of a history that has been almost, but not quite, forgotten.
By Anne C. Wheeler, PhD, 2019
Anne is an associate professor of composition & rhetoric and chair of the Department of Literature, Writing, and Journalism at Springfield College.
 King Philip’s War,” History.com Editors. HISTORY. A&E Television Networks https://www.history.com/topics/native-american-history/king-philips-war. Published 2009, updated 2019. Date accessed December 9, 2019.
 1636-1675. Early History of Springfield, an Address Delivered October 16, 1875, on the Two Hundredth Anniversary of the Burning of the Town by the Indians. Henry Morris. F.W. Morris, Springfield, Massachusetts, 1876. Page 34.
 Brethren by Nature: New England Indians, Colonists, and the Origins of American Slavery. Margaret Ellen Newell. Ithaca: Cornell University Press, 2016. Page 5.
 Ibid p. 117
 History and Genealogies of Ancient Windsor, Vol. 1, Henry Reed Stiles. Hartford, Conn. : Case, Lockwood & Brainard Co., 1891. p. 422
 “Connecticut’s Contested Early 17th-Century Landscape,” Connecticut Explored Vol. 17 No. 3, Brian Jones and Kevin McBride, p. 19
 Henry Wolcott Jr. estate inventory, 1680. Connecticut. Probate Court (Hartford District); Hartford, Connecticut. Accessed via Ancestry.com. Connecticut, Wills and Probate Records, 1609-1999 [database on-line]. Provo, UT, USA: Ancestry.com Operations, Inc., 2015.
 Newell. p .13
 Ibid. p. 11
 Ibid. p. 14
 The History of Springfield in Massachusetts for the Young, Being Also in Some Part the History of Other Towns and Cities in the County of Hampden. Charles H. Barrows. Connecticut Valley Historical Society, Springfield, Massachusetts, 1911. Pages 74-75.
 “King Philip’s War,” History.com