Randolph moved to Boston to live with Coolidge and her husband hired Cottrell out to Thomas Hewitt Key at the University of Virginia.

[4][5] Key lived in Pavilion VI on the University of Virginia campus and Cottrell served as his wife's maid and nurse.

He immediately clashed with other faculty at the university and was described by Coolidge as "one of those Englishmen who have succeeded in making their nation hated in every part of the known world."

Key's intention was to free Cottrell, but Virginia law required freed slaves to leave the state within a year or face re-enslavement.

In 1850, when the status of a number of free Blacks in Virginia was legally questioned, Cottrell testified that she was a slave belonging to Key.