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The purpose of this paper is to explore the political, toy manufacturing, and educational activities of Caroline Louise Pratt (1867‐1954), founder of the Play School (later renamed City and Country School), New York City.

The paper reviews previously unreported biographical material and draws on a number of Caroline Pratt's own writings, combining results of archival text research and digital searches.

Newly available data sources on Caroline Pratt's 1896‐1921 life show her to be more of a social reconstructionist than previously concluded. This research demonstrates that it was Pratt's feminist, socialist and trade unionist ideals, transformed into educational aims, that formed the core of her educational work.

This investigation is limited to Pratt's activities during the years 1896 to 1921.

The internet has provided ready access to a wealth of newspaper and journal documents. The ease of access has no precedent, and the volume of newly available data sources has brought opportunities for reinterpretation and rewriting of the history of education. Yet even more new data will inevitably become accessible. This paper provides insights into how previously unresearched documents, now easily found through digital research, can enhance understanding of the contributions of Caroline Pratt.