The first major federal effort to remake territorial property came through large sales to land companies. This chapter recounts this history through the stories of three land companies: the Tennessee Company, the Ohio Company, and the Miami Company. The Tennessee Company represented what the federal government hoped to avoid. Created by speculator Zachariah Cox, the Company purchased millions of acres of land in Georgia’s Yazoo sale. Cox then spent the next decade challenging federal authority, threatening Native nations, bamboozling investors with dubious title, and asserting his own sovereignty in the southern borderlands. When it created the Ohio and Miami Companies in the Northwest Territory, the federal government sought to avoid such outcomes. The two companies, headed by Rufus Putnam and John Cleves Symmes, promised to distribute title systemically while also preserving peace with Native peoples. Yet this supposedly mutually beneficial relationship did not work out. Both companies felt abandoned and betrayed by the federal government when war with the Northwest Indian Confederacy ensued. Yet, like the Tennessee Company, the Ohio and Miami Companies also both succumbed to the lure of profit on bare promises of future title, creating still more property confusion and uncertainty that fell to the federal government to resolve. The experiment’s failure led Congress to reject large-scale land sales as a viable solution to the territories’ property uncertainty.