Partly because of his Florence Leopold's ill health, partly due to the family's wealth, Nathan, like his friend Richard Loeb, was raised by a series of nurses and governesses. Nathan's first governess was a girl named Marie (Mimie) Giessler. Giessler was Leopold's nurse for 5 years. After Mimie left, a girl named Pauline Van den Bosch filled the vacancy. Pauline, a Christian, introduced Nathan to the Christian saints. Nathan, at five years of age, took a keen interest in the saints and set about categorizing saints and religions. He would have the chauffeur drive him to various churches in the neighborhood. At about this time he also became interested in the life of Christ and of crucifixes. "The idea of nailing somebody to something was very appealing to me". Pauline only stayed on for six months.
The third and final governess was an Alsatian woman named Mathilda Wantz. Nathan nicknamed her "Sweetie." Sweetie only spoke German.
Wantz 's impact on Nathan and Sam was significant. When Nathan stole some stamps from a cousin, instead of punishing him, she blackmailed him, to cover for her days off,etc. She bathed with Nathan and with Sam and was "familiar" with their bodies. She wrestled with the boys as reward for good behavior.
Wantz was let go when Nathan was twelve, when his mother caught her dumping an ill Nathan out of bed one morning. Nathan was stretched out between his brother's and his own bed and Wantz pulled the two beds apart just as Florence Leopold stepped to the door.
Young Leopold had difficulty with his peers. His first two years of school were attended at "Miss Spade's", a once co-ed but at the time Nathan entered, an almost all girls school, to which he and one other boy were the only boys. He was then transferred to "Douglass School", a public school where he was told by his mother not to touch anything and not to use the bathroom.(which resulted in an accident). Nathan was the only pupil at Douglas that lived on Michigan Ave. Michigan Ave in the '20's, was a bit similar to the Michigan Ave of today's "Magnificent Mile." Those that lived on Michigan Ave were wealthy. Nathan was also the only pupil who was accompanied to school every day by a governess. These factors led to his assumption of superiority to his classmates.
When the Leopold family moved from Michigan Avenue to the Kenwood neighborhood, two blocks away from another wealthy Jewish family, the Loebs, Nathan transferred to the private Harvard Prep school and progressed rapidly. He was taunted as "The Great Nathan", "Crazy Bird", and "Flea".
When Nathan was 15, he began going about with a group of 6 or 7 boys, of which Richard Loeb, who was attending the University of Chicago as a freshman, was a member. Loeb was a year younger than Nathan. At first the boys disliked, even detested one another. But this quickly changed. By the time Nathan entered the University of Chicago at age 15 years, ten months, he and Loeb were friends. (1920-1921). By February 1921, they were, what Leopold described as "firm friends".
Both Leopold and Loeb transferred to the University of Michigan at Ann Arbor the following year (1921-1922), where they roomed together until Richard moved into the Zeta Beta Tau fraternity, into which he was accepted.
Loeb was accepted to the frat under the condition that he break friendship with Leopold. Rumors had spread about the two. The rumors took the form of letters written by a boy named Hamlin Buchman. Buchman worked summer's at the Loeb estate in Charlevoix. One night after they'd been drinking, Richard got up to go to the bathroom and got into bed with Nathan. Buchman wrote letters to Nathan's brother, Richard's brother, and the Zeta Beta Tau fraternity.
Leopold and Loeb remained friends, and did get drunk together a number of times at Michigan, however, they agreed not to be seen alone together in public. If they went anywhere together, they would take along a "chaperone". Loeb later stated that this was solely on the advice of his brother, Allen, who had been called to Michigan to straighten out the mess.
The year at Ann Arbor then, was anything but pleasant for young Nathan. His mother had just died and he missed some school at the biginning of the year. When he got to school, his best friend, with whom he expected to spend a great deal of time, was cold to him, as a result of the rumors. Richard moved into the frat. Nathan was "led along" by one frat, but they didn't pledge him. In mourning for his mother, he wasn't supposed to play cards, but this ban was lifter by his father, after some outside prompting.
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