Tobias Lear was George Washington’s trusted secretary. Over the years in which he served Washington—he took care of Washington’s most intimate affairs until the president’s death in 1799—Lear was responsible for scouting suitable housing for the Washingtons up north; for handling Washington’s more delicate correspondences; and for assembling the staff, both enslaved and indentured, who would care for the Washingtons in their many residences. Lear later assumed the role of chief of staff once Washington ascended to the presidency and moved with his wife and young son to the Executive Mansion at High Street in Philadelphia, the nation’s temporary capital. Lear handled matters of the utmost discretion for the Washingtons—including the controversial decision to “rotate” or “shuffle” the Washington’s slaves between Philadelphia and Mount Vernon after learning of a law which allowed any adult enslaved man or woman to claim their freedom after six months of living in Pennsylvania. Lear, in his letters to his employers, revealed a certain ambivalence about the institution of slavery—yet his mind was governed by a deeply-ingrained sense of paternalism, or the erroneous and racist belief that white slaveholders knew what was best for the Black men and women they kept enslaved. He, like the Washingtons, believed that freedom would be too great a burden for any Black man or woman to bear.