During the 1790s, Henry and another close friend, John Askin, were interested in land speculation in Ohio. One of their ventures, known as the Cuyahoga Purchase, came to naught when the Ohio Indians from whom the land had been acquired at the end of the Northwest Indian War refused to bring forth their land claims at the Treaty of Greenville. The deeds which had been obtained by Henry and his associates were considered invalid, causing Henry to moan, "We have lost a fortune of at least one million of dollars."