In the early hours of May 21, 1905, a wealthy and socially prominent Harvard senior named Benjamin Joy was arrested as an accomplice in the theft of a bronze plaque from the Phillips Brooks House. The theft was one in a long history of “stunts” perpetrated by a Harvard Secret Society known as the “Med. Fac.,” its members taken from the most prestigious of the Harvard clubs and representing the elite of New England society. Despite all varieties of mischief, ranging from practical jokes to criminal vandalism and use of explosives, no member of the Med. Fac. had been apprehended while engaging in any activities for forty-five years. Many presumed this was the result of “social pull,” an indulgent University’s laissez-faire approach based on a vested interest in shielding the sons of benefactors. Some suspected the university’s failure to act aggressively to combat the society was owing to members of the faculty and administration themselves being members. Joy’s arrest set off a firestorm, since most in the academic community, patience long worn thin from the shenanigans, favored immediate expulsion. Byron Satterlee Hurlbut, as Dean of Students, had a major fire to put out, and he relied upon his newly appointed assistant, Edgar Huidekoper Wells—secretly a former Med. Fac. man himself—to negotiate a compromise. The bargain: if the Med. Fac. dissolved and turned over their records and stolen property, Joy would not be expelled. Complicating matters, the records included incriminating journals documenting the Society’s exploits over the years and the individual “doctors” involved. The final settlement, a controversial one, was accepted before that year’s Class Day ceremonies. Behind the scenes, it was another story entirely. Demonstrating “the power of sentiment even for bad traditions,” wealthy and well-connected alumni in business and finance in Boston and New York were not all willing—nor were they under any obligation—to accept the conditions of the settlement. In fact, only Harvard’s end of the agreement was upheld, an embarrassing fact that the University authorities tried to keep under wraps through misinformation and subterfuge. None of the trophies or records of the organization were turned over to the University authorities as all had been led to believe; instead, over the ensuing years they were hidden in safety deposit boxes and storage facilities, as well as in a trunk in the basement of a physician’s home in Manchester, Massachusetts. The Society’s end of the bargain was not honored for nearly thirty-five years, and only then primarily due to the efforts of well-respected socialite lawyer, yachtsman, and big game hunter, Charles Pelham Curtis, in conjunction with the Harvard historian and Professor Samuel Eliot Morison, who acted as an intermediary for the University. Meticulously researched and relying on primary correspondences that were not made public until 2000, as well as the actual records of the Med, Fac., also held under seal in the University Archives until 1976, “A Theft of Privilege” is a tale of social privilege and deceit involving the scions of the most prominent New England families. The events of this collegiate drama, as well as revelations concerning the men behind some of the most notorious “depredations” ever to take place in a college setting, are detailed for the first time within the overall context of Harvard during the Gilded Age, a period during which both social stratification and a burgeoning democratization came into fierce conflict.