Leopold and Loeb

Leopold and Loeb

Leopold & Loeb in Chicago Tribune

Leopold and Loeb taken to prison

Leopold and Loeb Relationship

To examine the relationship between Leopold and Loeb – Babe and Dickie – there is no greater source than the famed Hulbert-Bowman report.  In preparation for the trial, the defense team enlisted the aid of two physicians who were not psychiatrists, Harold S. Hulbert and Karl M. Bowman. They examined Leopold and Loeb for fourteen days, probing and measuring their body functions, mentality, intelligence, their family histories and fantasies, as well as the then-popular matter of the function of their endocrine glands to appraise the physical and mental basis for their behavior.

The report covered every aspect of their childhood and personalities.  The most intimate facts of Loeb’s and Leopold’s lives, their fixations, their “master-slave” relationship and their sexual relations were anchored in childhood fantasies and intellectual precocity absorbed into compensations for fears of physical inferiority. The report forced an entire revision of the assumed relationship between Leopold and Loeb; Loeb was now the "master” criminal and Leopold his willing slave and subordinate. This seemed initially to be the shocker: “Loeb is the king. It is he who has been the master-mind throughout. He is almost without emotions.... He has always been fond of crime stories.”

Years later, Leopold was interviewed and admitted that in fact the King-Slave relationship was reversed.  Leopold claimed to take the role of King.  His admission likely had more to do with their sexual relationship as he was the instigator of sexual activity.  It is generally accepted that in criminal behavior, Loeb was the leader and Leopold the follower.  

The Hulbert-Bowman report, which was supported by the testimony of Dr. White, revealed that Leopold and Loeb entered into a compact to exchange sex and crime.  Loeb’s interest was to commit crimes, while Leopold’s was more his sexual attraction to Loeb.

First Meeting

Leopold told Loeb that Loeb was the smartest young man in the world today, and although Loeb did not accept it as absolutely true it pleased him tremendously and endeared Leopold to him at that time.

Leopold and Loeb met in the Spring of 1920, Leopold was 15 and Loeb 14.  They were nearly contemporaries in age, but younger than the social and academic circles they traveled as both were entering the University of Chicago at that time.  They were attracted to each other’s intelligence and mutual feelings of superiority over others their age.  They both harbored fantasies: Loeb for crime and Leopold of a master-slave relationship, which would also include intimacy.  Through their relationship they could enable and enact each other’s fantasies.

Sexual Relationship

From the Hulbert-Bowman report, it was Leopold’s interest in physical intimacy with Loeb that initiated the first half of their compact.  It was sex first and then crime.

Not long before they met, Leopold stated in the Hulbert-Bowman report that he had his first sexual relations with both other boys and a woman.  Here are two excerpts:

“When he was fifteen years old he (Leopold) was a member of a group of seven or eight boys. The patient went around with one of these boys a good deal and they practiced mutual masturbation a number of times.”

"When he was fifteen and a half years old he had, for the first time, sexual relations with a woman. It was the custom among the boys of his group, who had automobiles, to take a friend and drive out and pick up two girls and then endeavor to have sexual relations with them. He had been out on a number of such parties but the girls they had secured would never permit anything more than fondling or caressing. That night he and his friend picked up two girls who at once, in a business like way, offered sexual relations in the car for three dollars or at their homes for five dollars. The patient sat in the back seat caressing and petting the girl who was with him. He was doing this rather, perfunctorily and he had no erection. However, he did have an extreme desire to urinate, and he got out of the car and did urinate. When he returned the girl raised her skirts and said "Let's go". The patient found himself quite impotent and was greatly chagrined at this. He was so embarrassed at this that he made his comrade solemnly swear he would never reveal his secret."

Leopold and Loeb initiated the sexual relationship on a train ride from Chicago to the Loeb summer home in Charlevoix.  While on the train, they shared a sleeping berth.  The act was Leopold inserting his penis between Loeb's legs. According to the Hulbert-Bowman report, "It was his first time with his penis between Loeb's legs and he found that it gave him greater pleasure than anything else he had ever done."

Rumors of their Relationship

In the Fall 1921, Loeb transferred to Michigan. Leopold's admittance was delayed by illness.  He entered in October, that situation being quite heavily documented in the trial transcript. Leopold went to Michigan, talked with the dean, then bolted over to take a physical where his blood pressure was exceedingly high. Leopold entered Michigan, and roomed with Richard, with whom he expected to continue on the same terms.

However, he found Richard cold to him in public. Richard finally informed him of the situation. There were rumors that the two of them had engaged in homosexual relations, and they were a "couple of cocksuckers." Richard was trying to get into Zeta Beta Tau fraternity and they had informed him that although they didn't believe the rumors, Loeb should try not to be seen with Leopold too much. Loeb's brother, Allen, even went to Michigan to speak with the fraternity and assure them his brother was quite normal and the incident was innocent and misunderstood. Allen also encouraged Loeb to not be seen with Leopold very much.

Loeb told Leopold, and they, in their classic pattern, formed an agreement. They agreed to remain friends, but not to be seen alone together in public, or in any way that could be misunderstood. They even made sure to drag along a "chaperone" or a third party, whenever they went anywhere together. They did, however, get drunk a number of times together.


It was Loeb’s fantasy of being a master criminal that launched their initial acts, mostly vandalism and petty thefts starting in 1921.  In 1923 is when their criminal acts began to escalate and become grander.

After his mother’s death, Leopold transferred back to the University of Chicago while Loeb finished his degree at the University of Michigan.  In the Fall of 1923, Loeb returned to Chicago and their relationship, especially in crime, resumed in earnest.

Both were attending post-graduate classes in law at the University of Chicago.  They would attend classes during the day and then return to their homes for dinner and time with their families.  They would appear to prepare for bed, but then sneak out of their houses, meet up around 1:00 am, have their “adventures” and return before dawn.

Sometimes Nathan would drive around and Dick would throw bricks through store or car windows. Dick smashed the window of a Walgreens once. And once he threw a brick through the windshield of a car. Apparently, a man and woman were making out in the back and the guy jumped up and shot at them.  They made prank phone calls and called in false fire alarms.  They graduated to arson and set several abandoned shacks on fire.

In November 1923, they drove back to Ann Arbor and burglarized Loeb's former fraternity house, the Zeta Beta Tau house, in Ann Arbor.  In the burglary, they stole a portable Underwood typewriter, which later Leopold would use to type the ransom notes.

On the ride back to Chicago, they first discussed kidnapping. Originally, the idea was gotten out of anger towards a certain person, theoretically Hamlin Buchman, who had spread the rumors about them being homosexual two years previous.


Their relationship was not always smooth.  They fought over subjects that were "disharmonious" to them.  In theory, this would be sex and crime. Leopold disliked the risk involved in crime. Whenever he balked, it was because of risk, such as with the incident with the thefts, although he caved in on that eventually.  Theories state Loeb was unhappy with Leopold's demands for sex.  Loeb was also upset at Leopold for not obeying his orders to go through with their criminal activity. In Richard's mind, he was the master criminal. His role was that of master planner and director.

Below is a letter that resulted from one of their fights over a proposed plan for New Year's 1923. Leopold and Loeb had previously planned to spend it together. Loeb, however, changed the plan and decided to go out with Dick Rubel and two young girls. A fight ensued, involving Rubel. Leopold made some comment to Rubel which resulted in Loeb accusing Leopold of betraying a confidence, of "treachery".

October 9th, 1923

Dear Dick:

   In view or our former relations, I take it for granted that it is unnecessary to make any excuse for writing to you at this time, and still am going to state my reasons for doing so, as this may turn out to be a long letter, and I don't want to cause you the inconvenience of reading it all to find out what it contains if you are not interested in the subjects dealt with.

   First, I am enclosing the document which I mentioned to you today, and which I will explain  later. Second, I am going to tell you of a new fact which has come up since our discussion. And third, I am going to put in writing what my attitude is toward our present relations, with a view of avoiding future misunderstandings, and in the hope (which I think is rather vain) that possibly we may have misunderstood each other, and can yet clear this matter up.

   Now, as to the first, I wanted you this afternoon, and still want you, to feel that we are on equal footing legally, and, therefore, I purposely commited the same tort of which you were guilty, the only difference being that in your case the facts would be harder to prove than in mine, should I deny them. The enclosed document should secure you against changing my mind in admitting the facts, if the matter should come up, as it would prove to any court that they were true.

As to the second. On your suggestion I immediately phoned Dick Rubel, and speaking from a paper prepared beforehand (to be sure of exact wording) said: "Dick, when we were together yesterday, did I tell you that Dick (Loeb) had  told me the things which I then told you, or that it was merely my opinion that I believed them to be so?" I asked this twice to be sure he understood and on the same answer both times (which I took down as he spoke) felt that he did understand. He replied: "No, you did not tell me that Dick told you these things, but said that they were in your opinion true."

   He further denied telling you subsequently that I had said that they were gleaned from conversation with you, and I then told him that he was quite right, that you never had told me. I further told him that this was merely your suggestion of how to settle a question of fact, that he was in no way implicated, and that neither of us would be angry with him at his reply. (I imply your ascent to this.) This of course proves that you were mistaken this afternoon in the question of my having actually and technically broken confidence, and voids my apology, which I made contingent on proof of this matter.

   Now, as to the third, last, and most important question. When you came to my home this afternoon I expected either to break friendship with you or attempt to kill you unless you told me why you acted as you did yesterday. You did, however, tell me, and hence the question shifted to the fact that I would act as before if you persisted in thinking me treacherous, either in act (which you waived if Dick's opinion went with mine) or in intention.

   Now, I apprehend, though here I am not quite sure, that you said that you did not think me treacherous in intent, nor ever have, but that you considered me in the wrong and expected such a statement from me. This statement I unconditionally refused to make until such time as I may have become convinced of its truth. I never did. But you shouldn't have said those things and you should apologize. You acted hastily

   However, the question of our relation I think must be in your hands (unless the above conceptions are mistaken) inasmuch as you have satisfied first one and then the other requirement, upon which I agreed to refrain from attempting to kill you or refusing to continue our friendship. Hence I have no reason not to continue to be on friendly terms with you, and would under ordinary conditions continue as before.

   The only question, then, is with you. You demand me to perform an act, namely, state that I acted wrongly. This I refuse. Now it is up to you to inflict the penalty for this refusal- at your discretion, to break friendship, inflict physical punishment, or anything else you like, or on the other hand, continue as before. The decision therefore, must rest with you. This is all of my opinion on the right and wrong of the matter.

   Now comes a practical question. I think that I would ordinarily be expected to, and in fact do expect to continue my attitude toward you, as before, until I learn either by direct words or by conduct on your part which way your decision has been formed. This I shall do.

   Now a word of advice. I do not wish to influence your decision either way, but I do want to warn you that in case you deem it advisable to discontinue our friendship, that in both out interests extreme care must be had. The motif of "A falling out of a pair of cocksuckers" would be sure to be popular, which is patently undesirable and forms an irksome but unavoidable bond between us. Therefore, it is, in my humble opinion, expedient, though our breech need be no less real in fact, yet to observe the conventionalities, such as salutation on the street and a general appearance of at least not unfriendly relations on all occasions when we may be thrown together in public.

   Now, Dick,. I am going to make a request to which I have perhaps no right, and yet which I dare to make also for "Auld Lang Syne." Will you, if not too inconvenient, let me know your answer (before I leave tomorrow) on the last count? This, to which I have no right, would greatly help my peace of mind in the next few days when it is most necessary to me. You can if you will merely call up my home before 12 noon and leave a message saying "Dick says yes," if you wish our relations to continue as before, and "Dick says no," if not.

   It is unnecessary to add that your decision will of course have no effect on my keeping to myself our confidences of the past, and that I regret the whole affair more than I can say.

   Hoping not to have caused you too much trouble in reading this, I am (for the present) as ever,



The psychiatrists repeated the same line. "In my study of this tragic situation I can see no way of understanding it except as one tries to understand the association between the two defendants."

What the Hulbert-Bowman report concluded was that the combination of their personalities completed each other.  Neither could have killed Bobby Franks or committed any of their petty crimes without each other.  The compact and the King and Slave fantasy was the heart of how each of them could follow the other.  Only through understanding the fantasy and the compact, said Dr. White, can one understand how Leopold would put himself in the position to do absolutely anything Richard Loeb suggested.

"Dickie Loeb, the guy who ruined my life ... Still, I gotta tell you something. You know what, he was really a swell guy, the best friend I ever had."


In 1932, Leopold and Loeb were reunited at Statesville Prison after being separated for years.  They started a school at the prison and taught fellow prisoners.  The school became very popular and a gained media attention.  In 1936, Loeb was killed by a fellow prisoner James Day.

"During the four years preceding his death, Dick and I were, as I have said, as close as it is possible for two men to be. Whatever happened to be our individual assignments, we worked together as a team. The school was a joint project, but we worked together just as surely on the library, the greenhouse, the Sociological Research Office. And we played handball as partners, and bridge. But much more than that, we planned together and shared our individual problems. No matter what our separate activities for the day might be, we made it in invariable practice to have a twenty minute talk immediately after breakfast each day. We cut everything up together, whether it concerned him, or me, or both of us. We had no secrets. Often we disagreed about something. Usually, after talking it out, we were able to reach agreement. For the rare cases when we couldn't, we adopted an ironclad maxim: Safer counsel shall prevail. If, after hashing a subject over, it became apparent that we could not agree, we did whatever was safer, more conservative. I'm sure we saved ourselves a lot of trouble that way."