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When Elizabeth Freeman ("Mum Bett"), a slave in Sheffield, Massachusetts, successfully sued for her freedom in 1781, she set gears in motion for challenging the existence of slavery in Massachusetts and declaring it unconstitutional, but the institution was never officially abolished in this state. When Gilbert Speakman wrote to Aaron Willard in 1788 about the slave Jube's intentions to leave his master, the legal issues regarding the institution of slavery in Massachusetts were still murky and confusing. It appears that Jube had left his "Master Joshua", considered retuning to him, but changed his mind and chose to remain with Speakman. Aaron Willard was reminded that if Jube decided to move on, Speakman would try to convince Jube to stay but Speakman no longer had any "authority" to retain Jube or return him to "Master Joshua".

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