“Both the original Nine Squares plan and the subdivision were designed with a clear, fixed plan in mind. But it took over sixty years to fully recognize the plan they laid out in 1784. Visitors to the city near 1800 could still remark that only ‘most’ of the squares were divided by cross streets.
High Street, the third new north-south street after Orange and Temple, was both the first and the last highway laid out in the Nine Squares. The street was advanced block by block; the first block was laid out in 1784, but the last one was not laid out until 1827.
Unlike the other two north-south streets, which appear to have been laid out in the northernmost blocks first, the townsmen tried to lay out High Street beginning in the southernmost block. Lower High Street was only laid out forty feet wide, as opposed to Orange and Temple streets, both of which had a width of fifty feet.
This may have been an adjustment made because of the crowdedness of the lower block, necessitating a narrower road to avoid houses and barns. The same three West Haven men who had appraised the lands affected by Orange Street and Temple Street also appraised the lands which were taken on the lower block of High Street.
But instead of awarding no compensation, this time, the committee referenced an unusual reason why the damages were settled: ‘We the subscribers freeholders having agreed and by exchange of land settled the matter of damages respecting their two lots, demand no damages…’
As with Temple Street and Orange Street, no monetary damages were awarded. This is the only deed which explicitly invokes the ‘offsetting benefits’ doctrine, stating that the benefits of the new highway outweighed the damages that some of the landholders suffered.
But less straightforward is the reference to an ‘exchange of land’ between the two damaged owners. It seems that Lucas and Prescott might have had claims against the town stemming from the creation of High Street, but that these claims were relinquished after a transaction between them.
Hunting through the records, it becomes evident that the transaction was actually very complex, and designed to placate only one of the parties: James Prescott. The transaction provides a clear example of how the selectmen of New Haven may have dealt with possible problems related to their street plan: with a lot of extralegal deal-making.
In the fall of 1784, James Prescott was a party to two land deals on the same day: one, a transfer from New Haven Mayor Roger Sherman to him, and another reciprocal deed between himself and Mary Lucas.
From the two deeds, Prescott appears to have had a house and shop between some of Lucas’s land and Sherman’s residence. His lot was not very deep; his neighbor, Mary Lucas, seems to have owned land bordering his lot on both its west and south sides.
In the transfer, Roger Sherman swapped a piece of his land fronting on Chapel Street for a roughly equally-sized piece out of Mary Lucas’s land behind Prescott’s lot. Lucas and Prescott swapped all of their land on different sides of the new street, so that Lucas would have all of the land on the west side of the street and Prescott would have all of the land on the east side.
The following diagram indicates the result of the swap:
In this transaction, two leaders of city government—Roger Sherman and James Hillhouse—had to give up land to relocate Prescott’s lot. Sherman may have been involved out of civic responsibility, but also family ties: he was married to James Prescott’s sister and, a decade later, went into business with his brother.”
-Excerpt and (above) diagram courtesy of “The Failure of America’s First City Plan,” by Maureen E. Brady, published in the Urban Lawyer, 2014. (top) Image courtesy of Lincoln Financial Foundation Collection, Allen County Public Library, Fort Wayne, Indiana, by way of Digital Public Library of America, “CDV, Roger Sherman residence in New Haven, Connecticut,” by Major Moulthrop, no date