Exploring Motivations For Murder: The Making of American Criminals

I was privileged to talk with the writer/director and the two stars of the upcoming Leopold and Loeb film American Criminals. Here’s what they had to say about their movie.

After attending The American Musical and Dramatic Academy, writer/director Aaron Warr has been working in the industry and writing scripts for 20 years. This will be his second feature film. Warr first heard about the Leopold-Loeb case when watching a documentary on the History Channel, and it spoke to him. “I was immediately drawn to the story,” he recalled. “There were so many layers each character could bring to the script. Add in what was going on during the roaring 20’s, and it was impossible to not dig further.”

Warr said he was particularly struck by what the story implied about the relationships between parents and their children: parents putting “pressures on children at an early age into teen years and living vicariously through their own children.” But also the reverse: the disrespect children showed to their parents, “the demands they make and how they are given everything they want.” Warr saw this reflected in the Leopold-Loeb case as well as in many families he knew, and wanted to address the recurring intergenerational issue that can lead to terrible consequences.

Though many past retellings of the Leopold-Loeb story have focused almost exclusively on the killers, without paying much attention to the time period or place, Warr is interested in exploring “the racial turmoil going on at the time. We cannot tell a story of this caliber without showing the issues not just with African Americans but, Polish and Jews and Irish and others of the day.”

Actor Bing Brazeau, who portrays Leopold, also found the aspects of racism and homophobia important to explore. He said that he sometimes finds it difficult to get into Leopold’s headspace, as Leopold felt that murder was no big deal, but “it’s helpful that there was an outpouring of hate, homophobia and anti-Semitism during the trial, so that hate directed to them feels unjustified. He feels like people are mad at me for no reason. It sucks that there was such a strong anti-Semitic and homophobic reaction against them, it muddles things, but it’s helpful because it provides the audience with places to emphasize and rage at the system.”

Also unique to American Criminals is that it’s based off of Leopold’s autobiography: Life Plus 99 Years. Others have tried to adapt the book before, including actor Don Murray, but Warr is the first person to move beyond a script and actually start filming. By pulling from both the book and his own research, Warr hopes to “show who these boys were first before they were convicted,” then moving beyond that to show how Leopold felt remorse, and the “salacious details of 1920s prison life and the horrible conditions,” Leopold and Loeb faced in Joliet and Stateville.

As the movie is based on Leopold’s autobiography, the focus is more heavily on him and the tragedy that despite his “intelligence, timidness and vulnerability, it was not enough to shield him from making a bad decision,” according to Warr. Brazeau, a Wisconsin native with a theatre background, has been enjoying the challenge of playing the complicated character. He explained that though Leopold is a bad person and a murderer, “his reasoning was rooted in love. I’ve never killed anyone over that, but there’s a relatability in that. I enjoy that I can create this link of empathy between this person who’s not up to a high moral standard: he’s a bad person, but for reasons that we all understand.”

Of course, there can’t be a Leopold without a Loeb, and Warr said he hopes to show in his movie “how he was the key manipulator of the two.” But Warr also wants to delve deeper into Loeb’s psyche, and explained that “good looks, arrogance and entitlement may appear to others that you have everything and you really don’t.”

Jake Schory, the Philadelphia native who plays Loeb, expounded on this: “Richard Loeb is a very intelligent young man, who’s probably too smart for his own good. The other side of him is just someone who probably went unchecked for too long and wasn’t given the proper comparison. From what I’ve read, he was compared to other people and was never good enough, so a lot of his actions are kind of: I’m doing this because I have something to prove to somebody. Whether that’s himself or a family member, but there is a very cocky, narcissistic energy to it.”

Together these two messed up individuals combined into “a powder keg waiting to explode,” according to Warr. He refers to the relationship as a “loveless love story” and Schory admits that he sometimes asks himself: “why are these guys even together? It seems like Richard hates him but at the same time is just obsessed with this guy. Not as much as with Nathan as with Richard, but there’s definitely almost like a pet and owner vibe. He’s keeping him around, he does care for him, but not as much as Nathan cares about Richard.”

Executive Producer Aric Diamani, Director of Photography Johnny Young, Jayce Chastsin as Bobby Franks, Bing Brazeau as Leopold and Jake Schory as Loeb on set

For the actors, photos and videos have been important pieces of research in helping them embody their characters. Brazeau said that seeing an image of Leopold smiling in the 1923 Kirtland’s Warbler footage struck him particularly. As he had only ever seen photos of Leopold looking bored or serious before, “it just gave me a revelation,” he recalled. “Nathan was not the most social person, he was awkward, quiet and pretty self-serious a lot of the time, but he wasn’t incapable of emotion. He wasn’t incapable of that smile.” Schory also found photos of Loeb helpful clues to his narcissistic personality and he and Brazeau sometimes recreated poses they saw in photos during the courtroom scenes.

American Criminals will be the first movie directly about the case to come out since Swoon in 1992. Like Swoon, it’s being filmed on a limited budget, and the crew and actors sometimes have to get creative to work with what they have. Brazeau recalled that during the scene where Leopold and Loeb pull up to the curb to pick Bobby up for his ill-fated car ride, the owner of the vintage car they were using wouldn’t let them drive it. They worked around this by “putting it in neutral while the grip and assistant DP pushed it into frame,” as Brazeau sat behind the wheel. The budgetary restraints haven’t stopped the location scouts from finding buildings and exteriors around Chicago and Illinois that are distinctive and evocative of the time period.

Both Schory and Brazeau praised the atmosphere on set and the talent of their colleagues. “Aaron’s awesome,” Schory asserted, “he’s such a good director and he’s such a talented writer. Everything that he does, he’s making sure that everybody is set and comfortable and ready to go with everything. He has a good way of allowing me and Bing to kind of give our input into what we think should go into the scene but he’s firm on his feelings on what he’s writing and on his work so it’s just such a great atmosphere.” Warr has been working to get this movie made for almost a decade and says that finally getting to work on it feels “like going to the doctor after having a toothache for 9 years.”

The movie is still in production and shooting will continue through the summer. Warr states that as this is a Chicago story, the premiere will happen in the city.

Photos courtesy of Aric Diamani

August 15, 2023 Update

Hey all, I’m working on a post that isn’t quite ready yet, so instead enjoy these pages, with everything I’ve been able to find related to Chess or Checkers within this sphere. Random? Possibly. But Albert Loeb was very into chess and I thought it would be a cool little look into a hobby of his that he shared with his children, and then checkers was kind of an extension of that. But if that’s not of interest, I should have the other post ready within a week or so, so you can look out for that.

Other news:

  • I’ll be speaking about my book and research at the Chicago History Museum on Thursday, August 24th at 2:30 Central Time. If you’re in town you can come in person, and if not there will be a livestream. Tickets are $10 for non-members, $7.50 for members of the Museum. You can check that out here.
  • I’ve added a Comics/Graphic Novels page to the fiction in celebration of the 2 new comics I’ve found inspired by the case. One is a 64 page horror comic from 1971 that mostly tells the real story, but often substitutes fabricated names or names/places from Compulsion. And, crazily enough, a 1985 Spider-Man comic that was inspired by the case!

August 8, 2023 Update: Audiobook and Interview

Hey guys, stopping in for an off-schedule post to update you on a few things.

  • An audiobook version of my book is out! It’s available on Amazon and Audiobooks.com (where you can listen to it for free with a free trial!) If you have a library card to a participating library, you can also listen to it for free on Hoopla!
  • I also did an interview that was posted today: Fascinating Nouns: Loeb & Leopold: Lies, Love & Lechery, on that page there’s also a link to a bonus conversation, Life After Loeb.

Hope everyone’s having a great week!

August 3, 2023 Update

Sorry for the late post everyone! Life has been really busy lately, and the post itself kept growing and growing, so it took longer to put together than anticipated. But it’s up now, enjoy learning about the food eaten and restaurants patronized by Leopold and Loeb in 1924!

Other updates:

  • A teaser trailer for the American Criminals movie dropped, you can watch that here.
  • I found 3 new (to me) fictional things inspired by Leopold and Loeb in the past couple weeks, one of them a super cool horror comic from 1971. I’ll be updating the Fiction page as soon as I can read them all in depth.
  • Thrill Me at the Island City Stage in southern Florida is having its premire tonight, tickets are available here.
  • An audiobook version of my Leopold biography will be releasing on August 8th! You can check that out here.

What and Where Leopold and Loeb Ate in 1924

Thank you to ellde2012 for this idea! Here I’ll be gathering up all the information I’ve been able to find on the restaurants that Leopold and Loeb visited and food that they ate in 1924, Bon Appetit!

(Barish’s) May 9 * May 31
Cinderella
Coconut Grove
Cook County Jail
Cooper-Carlton Hotel
Daley’s
Dew Drop Inn
Drake Hotel
Kramer’s Restaurant
LaSalle Hotel
Madison Park Hotel
Marshall Field’s
(Stein’s)
Weiss’
Windermere Hotel

Vocab:
A la carte: A meal where dishes are selected from a menu independently from each other-rather than a fixed bundle of courses.
Table d’hôte: A meal with a fixed price, usually a multi-course meal with several options to choose from.

May 9

1352 South Wabash Avenue

David Barish, the owner, described this establishment as a cigar store and lunch room, though it was described in one paper as a “bakery and delicatessen.” Barish ran it with his wife Gertrude and their family members.

Leopold and Loeb listed the public phone in this cigar store/lunch room as the number of Louis Mason, to be used as a reference when Morton Ballard was renting a car. So on May 9th when Leopold went in to rent a car for the first time, Loeb came in to wait for the call so he could pretend to be Mason and give a good reference. As described by the shop’s owner, Loeb came in around noon “and bought a slug and wanted to use the telephone. He walked up and bought some candy, a box of raisins, and said, ‘Can I wait here for a telephone call? I expect to be called back.’ I said, ‘Yes, sir.’ And he stayed around eating his raisins and waiting for his call.” He testified that Loeb stayed around waiting for his call for 30-45 minutes. During that time a man named Max Tuckerman told a story about a Masonic stag event he’d been to the previous night. And though neither Tuckerman or Loeb recognized each other, Loeb remembered and repeated the stag story when questioned.

May 21

Lunch

Kramer’s Restaurant
3459 Cottage Grove Ave

After renting the rental car, Loeb drove Leopold’s car and Leopold drove the rental to Kramer’s, and got there around 12:15. The pair put up the side curtains on the rental car, then went in for lunch and left around one.

I have been unable to find descriptions or photos of this restaurant.

Dinner

Dew Drop Inn

After the murder the pair ate hot dogs (called red hots in Chicago) and drank root beer in the rental car. They purchased the meal from the Dew Drop Inn, a roadside eatery.

The name ‘Dew Drop Inn’ was a popular one for restaurants and bars across the United States at the time, and in the 40s and 50s several Dew Drop Inns would become prominent music venues.

Alibi

In their alibis, Leopold and Loeb reported to the state’s attorney that on Wednesday, May 21st they had lunch downtown at Marshall Field’s, then went to the Coconut Grove for dinner.

Though we know they didn’t actually go to these restaurants on this day, I thought it would make sense to cover the places named, as they likely had eaten there at some point.

Marshall Field’s

There were many restaurants available inside this massive department store complex, though it’s likely that they would have gone to the Men’s Grill, a restaurant just for men (except on Saturdays, when accompanied ladies were allowed in) attached to the store for men. As most of the other restaurants were crowded with female shoppers and children, a men’s restaurant had been established to draw men in to shop in the men’s store, and give them an alternative to the, often crowded, other restaurants.

According to a 1931 guide: “It is a beautiful and impressive room, with a Tiffany fountain at its center. There are many circular, leather-upholstered booths, which afford pleasant nooks for business luncheon-conferences. Luncheon may be had here from 75 cents to $1.50, or a la carte.”

Other restaurants were gathered on the sixth floor of the main store and included the Walnut Room, Narcissus Fountain Room and Colonial Room, along with other lower budget and faster options. Most of these served buffet style meals.

Coconut Grove

I’ve been able to find very little about Chicago’s Coconut Grove, as it was overshadowed by its more famous/infamous locations in Los Angeles and Boston. But if it was anything like its counterparts, it was famed for its live music, large dance floor and live palm trees in huge pots.

May 22

Cooper-Carlton Hotel
53rd street and Hyde Park Boulevard

Leopold, Loeb and their friend Richard Rubel had lunch at the Cooper-Carlton Hotel on this date.

Leopold discussed it during his interrogation:

Q: Where did you have lunch?

A: Down at the Cooper-Carlton

Q: Who was with you?

A: Richard Loeb and Richard Rubel.

Q: Does Rubel board there?

A: No.

Q: Why didn’t you have lunch at home that day?

A: Because we had this arrangement of eating one day each week at the various places, and Rubel not living at home, generally taking us to some hotel. We knew we were going to have fillet mignon there, at a table d’hote dinner.

Below is an example of a menu for a table d’hôte lunch at the Cooper-Carlton from 1919.

May 28

The Cinderella
64th Street and Cottage Grove Avenue

Above you can see the exterior of the Cinderella, with its large sign and location close to the Tivoli Theatre.

According to Susan Lurie, she and Leopold ate lunch here on May 28th, walking there from the University of Chicago campus. The Cinderella was only a few blocks from campus and had its grand opening on May 1st, 1924, so when Leopold went there with Susan Lurie it was less than a month into its run. Chinese food was particularly popular in Chicago at the time, and The Cinderella was actually owned by a Chinese man, unlike many other Chinese restaurants that served Americanized approximations of Chinese food. The Cinderella also featured live music and dancing.

Lurie described her lunch with Leopold and it was reported about in several newspapers:

Chicago Daily Journal, June 2: “The thing that strikes me deepest is what occurred at a luncheon we had last Wednesday, the day before he was taken into custody. We met on campus and went to the Cinderella tearoom near by. He bought two newspapers and gave me one to read. At the table we spread the papers out and he said with a smile: ‘Let’s see what has happened in the Franks case?’ I said to Babe in a joking way that it would be a good joke for him to go to the police and confess the crime. He said it would be a perfect joke and that I would get the $15,000 reward.”

Chicago Tribune June 2: “But the thing that strikes deepest in my mind now is the luncheon we had last Wednesday, the day before he was taken into custody. We met on the campus and went to the Cinderella tearoom, close by. As we walked he bought two newspapers and gave me one to read. ‘Let’s see what has happened in the Franks case,” he said. He was smiling, almost laughing, as he said it.”

“His eyes ran down the columns of type. He seemed highly amused. Then he came to the part that referred to the anonymous letter written to Jacob Franks-the letter that called the father of the dead boy a ‘dirty skunk’ and threatened the life of his daughter. ‘That’s a good one,” Babe said. He laughed. He thought the fellow who sent the letter was a great joker.”

“I said to Babe in a joking way-I assure you it was just a bit of light conversation-that it would be a good joke for him to go to the police and confess to the crime. He said that it would be a perfect joke and that I would get the $16,000 reward. He laughed gayly over that.” “I said to him ‘You confess the Franks murder and I’ll claim the reward.’ We had been reading a newspaper about it. He laughed and said it would be a good joke. What a grim joke it turned out to be.”

Chicago Daily News, June 2: “The last time I saw Nathan was May 28, the day before he was taken into custody. We went to the Cinderella tearoom at 63rd street and Cottage Grove for lunch. Nathan bought two newspapers and gave one to me to read. ‘Let’s see what happened in the Franks case,’ he said.”

Miss Lurie described how she had said she would like to get the reward offered for the solving of the mystery– that she “could use the money” and how her companion suggested that he go to the police and confess the crime– just as a joke. “He was gay and lighthearted– and in his attitude there was not the slightest uneasiness while we discussed the case,”

May 29 and May 31

Hotel Windermere
1642 East 56th Street

Leopold and Loeb claimed that after morning classes on May 29th they ate lunch together at the Hotel Windermere. This information came pre-confession, and was mixed in between stories of the false alibi, so it could also be false, but I don’t see why or what they’d be covering up here by lying.

The Windermere had just opened a new building the previous year right beside the old hotel, and the new had the most modern amenities.

May 31

On May 31st, after showing the police around the murder route, they were taken to Hotel Windermere to nap. When they woke up they were asked if they were hungry and Leopold reportedly said: “Yes, I am very hungry.” A turkey dinner was served by the waiters of the hotel, and policeman guarding the teenagers made sure that the forks and knives were removed.

LaSalle Hotel
208 South LaSalle Street

While Leopold and Loeb were being interrogated at the LaSalle Hotel it seems that they mostly or exclusively ate food from the hotel’s restaurants. Above is a menu from the hotel’s Men’s Cafe from June of 1924, for a good idea of what they may have eaten.

On May 29th Loeb ate dinner downstairs in a restaurant, accompanied by a police officer, while Leopold was served upstairs in the hotel room where he was being interrogated.

While assisting police, some newspapers reported that Leopold and Loeb sent out for candy to be brought in for them to snack on.

Drake Hotel
140 East Walton Place

May 30

Crowe stated to the press that he didn’t mistreat either Leopold or Loeb while they were in his custody. He said that he took them to The Drake for dinner on Friday May 30th and one dinner bill for Leopold, Loeb and their police escorts, was $102. “I’ll impound hotel bills and records if necessary to show how decently we treated those boys,” Crowe said to the press.

This hotel offered many dining options, including The Italian Room which sold sandwiches, light lunches and had a soda fountain, The French Room, which served breakfast and tea and the main dining room, pictured above.

May 31

Leopold and Loeb returned to Barish’s restaurant on May 31st so Loeb could be identified.

“As they entered young Leopold saw the lunch counter “Let’s eat,” he suggested, but a moment later Richard Loeb entered.” When Mrs. Barish identified him as Louis Mason and described how he had waited for a phone call in the store “Richard turned pale. He trembled and fainted.” Once Loeb was removed, Leopold was allowed to eat.

This event was described by the Chicago Daily News in two ways:

“At the second stop, where Loeb was recognized as Louis Mason of the kidnapping day, he swooned so completely that he had to be taken to a hospital. At the same time, while the party was in a lunchroom, Leopold, famished from the long night of ordeal, was stuffing himself with doughnuts and milk.’”

“When Leopold walked in he looked around the place, and seeing the counter with food, exclaimed:

“Let’s eat,” and ordered a sandwich, some pie and coffee.”

These descriptions, one saying that Leopold ate doughnuts and milk and the other that he ordered a sandwich, pie and coffee, came from the same newspaper article. So what he actually ate is a mystery.

June 1st

Breakfast

Daley’s
807 East 63rd street

Along the murder route, Leopold, Loeb and their police escort began their day with a breakfast at one of Daley’s Restaurants, also called Daley’s Lunch Room, a chain of eateries founded in 1892. It’s mentioned specifically that on June 1st both Leopold and Loeb were taken to the Daley location at 807 East 63rd street. Today there is still a Daley’s Restaurant in this location, the last in the city. Being just a few blocks away from the University of Chicago campus, it’s likely a place both had eaten at before in very different circumstances. The location even advertised in the University’s yearbook.

Two newspaper stories describing the breakfast follow:

Chicago Herald-Examiner: “Leopold, who had not slept all during the night from the time he was brought to the station from the Windemere Hotel, smoked incessantly-so much so that his fingers were stained a deep brown from nicotine.

He was not nervous, however, and he laughed and joked. Loeb, on the other hand, was palpably disturbed. His face was white and drawn. He ate little or nothing, while Leopold made a hearty breakfast on scrambled eggs, doughnuts, rolls and coffee.

Leopold was served by a pretty little waitress whom he kidded incessantly, and who, true to her calling, kidded him right back. Many were the snappy remarks made by the confessed murderer and, let it be said, the waitress returned him as good as he gave.

After the meal, when the detectives were leaving, she asked a reporter what it was all about. He told her, naming the two boys. The girl staggered back, almost falling, and the color drained from her face.

“My God! And I served them!” she gasped.

Word of their presence in the neighborhood soon got around and several hundred persons were waiting when the party left the restaurant.

New York Herald Tribune: “Leopold, eating only rolls and coffee, joked with a waitress. Loeb ate oatmeal, toast and coffee in silence, speaking only in monosyllables to his police guard.”

Lunch (Leopold)

Weiss’ Restaurant
509 N Clark St

Also called Weiss Hungarian Restaurant, this was owned by Isadore Weiss, who died the following year. I haven’t been able to find much background on this restaurant, but we do have very detailed descriptions about conversations that took place when Leopold had lunch there with his police escort and a gaggle of reporters. This lunch was fictionalized in Meyer Levin’s Compulsion, in which he borrowed heavily from the Chicago Tribune’s account of the event.

Police officer Frank Johnson described this during the court hearing:

“On following day, Sunday went to Weiss’ restaurant. After lunch we went outside and I caught him by the arm, he said: “I want to thank you for not holding my arm in that restaurant.” “Well, I am going to hold it now.” “I wouldn’t run…If I thought you would shoot to kill why I might take a chance.” In the restaurant a lady at the opposite table said to a gentleman: “There is Nathan Leopold.” And Leopold got up from his chair and said “I beg your pardon, Madam, I am not Nathan Leopold. I have been embarrassed several times by being taken for him.” Then sat down and turned to me “How would you like to be able to lie like that?””

Police officer James Gortland described this during the court hearing:

“I was present with Sergeant Johnson in the restaurant on the same evening, and on our entry he sat down at a table about the middle of the room, in Weiss’ restaurant on Clark Street just about two blocks up on the west side of the street, we sat at a table in the middle of the restaurant, a table at the wall, the south wall, and Frank Johnson sat to the east, Leopold sat with his back to the west, and I sat alongside of him. At the table directly to the east was a couple sitting there, and the gentleman had his back to Johnson. On our entry we of course sat down, and the woman passed a remark to her escort, saying “There is Leopold.” Leopold overheard this remark, immediately jumped to his feet and said, “I beg pardon, lady, I am not Leopold; I have been mistaken for him a number of times.” Then he sat down. A little later some reporters came in and sat at the table directly-

Q Have you finished that conversation?

A Yes, sir

Q Did he say anything after he sat down?

A He made some remark about “what do you think about that lie” or something similar to that.

Q All right, then what happened?

A Why, he had a conversation there, a general conversation between the reporters at the next table and our table, in which something about what he was doing, I believe the matter was discussed, and he went on to say that he liked to eat everything, that he had ate roast dog, roast horse, had attended a Japanese wedding in Honolulu and things of that sort, then there was a discussion about the double “p” in kidnapping. One of the reporters said, “that is where you slipped, Nathan.” He says, “You mean ‘they’ slipped.””

The following is a quite long and opinionated article from the Chicago Tribune by Genevieve Forbes, describing the lunch:

Like Julius Ceaser, the youth finds it easy and pleasurable to speak of himself in the third person.

He was compelled to do this at supper last night, over at Weiss’ restaurant, 509 North Clark street, where he went in custody of Detective Seargents Frank Johnson and James Gorton[sic], so the other diners would not discover his identity. Later, however, he kept up the little comedy.

The seargents didn’t want him to talk to the folks who found a seat at his table. But he insisted upon conversation.

And his conversation had a focal point, just one, and that was Nathan F. Leopold Jr.

First, it was the question of food. He ordered herring, and explained, “No, I suppose you don’t like it; but then you aren’t Jewish.”

That was the point of departure for a recital of the bizarre foods with which he loved to tempt his palate.

“Then, I presume”-there was a lifting of the eyebrow as he said it-“then I presume, you’ve never eaten seaweed? Nor dog meat? Bamboo shoots? Then you evidently been in Hawaii.”

The student whose admitted search for ultimate adventures in sensations, revealed a parallel desire for strange foods, when he said, as from the heights:

“I wanted to try something of everything. And I did. Yes, I had desperately bad stomach cramps after that. But I went on a voyage immediately, and I never missed a meal.”

The others at the table, anxious not to be outdone, gastronomically, spoke of rabbit and squirrel and horse. But the lad cut in with a theory about foods and fancies.

“Curious, isn’t it,” he suggested, “that two of the sweetest meats of all, squirrell and rabbit are shunned by many who are repelled by them. It’s just tradition, and so many of our traditions are irrational, don’t you think?”

It’s a way he has, of ending a sentence with a question. The words, graciously, invite discussion. But the tone in which they are said indicates plainly that there is only ne side to the question and that 19 year old Natan F. Leopold Jr., has just enunciated that side.

He’s been called an “intellectual giant” so often that he’s begun to believe it. And when, in jest, they ask him for a synonym for the phrase, he replies, “What about Nietzchian colossus?” And nobody will ever know whether or not he was in earnest.

But he does grow serious, when, still in holiday mood, they challenge him for the equivalent of “infant prodigy?”

“Why not call Mr. Leopold a Thomas Babbington Macaulay?” and there was almost humility in the boy’s tone. Macaulay, he is perhaps recalling, was the infant prodigy of all times. The man with so gigantic a memory that he boasted that if all the texts of Virgil be destroyed he could rewrite them from memory.

One moment it’s Hawaiian sea-weed, the next the philosophy of pessimism as declared by Schopenhauer. One moment it’s an imperious command: “Boy, bring me a paper,”; the next a dissertation on atheism. One moment its amused disdaid for the silly heroes of modern plays; the next it’s the same arrogant spirit of these same silly heroes.

At least he seems to be. Perhaps, he has his tongue in his cheek all the time. For he says, from a superior level of patronizing tolerance:

“You newspaper folks. You’ve made me out a conceited, smarty, haven’t you?”

“But don’t you know,” and he seems the professor explaining a theorem, “don’t you know that when a man’s on the defensive he has to have a consistent attitude? Don’t you know that?” And he repeats the question until his opposition begins to “yes” him.

“Well, once a man on the defensive has adopted a certain policy, he’s got to stick. If you move any, you’ve got to take all your soldiers out of one trench and send them to the other. Don’t you see?”

Then, specifically of himself, he says.

“I have manifested certain attributes of character. You say I am conceited. That, I don’t care. Well,” he seems to be seeing lots more than he’s looking at, “well, it may be that, or it may be something altogether different.”

He gets more and more objective, and presently he says, as if he were asking what you thought of the ghost scene in “Hamlet”:

“What do you think of that letter ‘they’ wrote?”

Inwardly his listeners may be ready to slap him for a “smart aleck who knows pretty near everything.” Actually they fumble for words. He helps them out.

“Contrasted to the average kidnaping letter, it’s pretty good.” This with a note of finality.

“You see, the other letters, either naturally or purpously, are illiterate.”

Somebody suggests that the author misspelled “kidnaper” using two p’s.

The smile is serenely flippiant now as the student replies: “It is my understanding that the spelling ‘they’ used is the archaic English spelling.”

Still pursuing an impersonal discussion of the letter, he asks another question:

“From the point of view of psychology, what do you think of it? Does it instill fear and lead to action?”

Everybody starts to agree with him, but he anticipates them when he makes a laboratory report on the note that was sent to Mr. Franks some twelve days ago.

“Yes, there was nothing flamboyant in that letter. It was concise and well phrased. It instilled terror. And it certainly impelled action. It seems to me.”

As he is talking a man at the table takes out his pencil and makes a few marks near his soup plate. The picture is a fairly symmetrical eclipse with a grotesque, disproportionate off-shoot to one side that makes a hideous figure of what started out to be a thing of almost geometric perfection.

“That’s what that shrimp is. He’s not rounded out normally. One side of him’s sprouted out into that damned, misshapen thing, all emotionalism and intellectuality.”

But the “shrimp” has suddenly displayed a new facet. He turns the pseudo-moralist.

“It’s too bad,” he muses, “for a newspaperwoman to have to work on this story. It’s too sordid for a woman.”

And nobody asks him if it wasn’t a bit too sordid for the man who did it.

Leopold response (specifically to Compulsion book’s recreation of this scene based on this article)

“I’ve never eaten herring in my life — can’t stand it. Whole episode about eating with newsmen at a restaurant is false.”

New York Herald Tribune: At dinner to-night, seated with reporters and detectives, he gave a further insight into his taste for the obscure. Telling of a visit to Honolulu, Leopold related that he had eaten many strange dishes that others in the party would not touch. It had made him sick with fever, but he had [?] the tradition.

“So many traditions are stupid, aren’t they?” he remarked. “The one against cannibalism, for instance.”

Though this lunch clearly happened, because two police officers and two reporters described it, it’s somewhat odd that, even though many reporters seem to have been in attendance, I’ve only been able to find it described in two newspapers. Now, this happened on a Sunday, when most papers didn’t run (or if they did, the Sunday editions often weren’t microfilmed and saved) and I usually have only one edition of each paper. Maybe some editions carried this story, but by the time the papers came out on June 2nd, especially since that was the day of the inquest, it may have been seen as too unimportant to print.

Eating with State Psychiatrists

On June 1st in between going out to the various sites to help the police, Leopold and Loeb also chatted to psychiatrists brought in by the State’s Attorney in his office. At around 3pm they had sandwiches brought in for them, and during the court hearing State psychiatrist Hugh Patrick described this in extreme detail:

“During this time the young men had something to eat, they had a lunch. Mr. Loeb had a little table and Mr. Leopold was not given a table, and one of the police officers handed him a very cumbersome sandwich – I don’t know how thick it was, but it was a very unhandy thing to eat while held in the hand, and Mr. [Leopold] evidenced some little embarrassment how to handle this grub…and nobody seemed to notice his little embarrassment with this thing, and I asked him if he would like to change seats with me, as I was sitting next to a filing case which would serve very well as a table. He thanked me very pleasantly and we made the exchange.

Then afterwards I wanted a drink of water. The fact of the matter is that all this recital had made me a little dry in the mouth and there was not any glass in sight. The two young gentlemen had all the available drinking vessels, and I asked Mr. Leopold if I might use one of his glasses and he very pleasantly gave it to me..and I took a drink of water and then I asked him if he would have the drink, and he said he would. I filled the glass at the water cooler and returned it to him and he received it very politely and pleasantly.

After Mr. Leopold had finished his lunch, he had about half a glass of water and he took a small bottle from his pocket and dropped some fluid, drop by drop, into his glass. That looked rather interesting to the doctors, and the State’s Attorney stated to us that was aromatic spirits of ammonia and asked Mr. Leopold if that wasn’t it, and he said it was. He drank that.”

This was also described, in much less detail, by State psychiatrist Archibald Church:

“Very shortly after Loeb’s entrance, both young men were supplied with a luncheon which they ate intermittently during the course of the interview during the next half hour or hour.”

Cook County Jail

While Leopold and Loeb typically ate from a local restaurant, they did occasionally eat the jail food as well.

The 1922 Cook County Jail Survey reports that typical meals for a day (though they acknowledge that the meals change somewhat day to day) were:

Breakfast: Clear coffee, duffer (bread)

Dinner: Beef stew, potatoes, vegetables, carrots, turnips or cabbage

Supper: Coffee, duffer, or soup and duffer.

For the month of April, 1922, the menu included mostly fish, sausage, chuck (meat), corned beef, bread, rice, peas, beans and potatoes. It was noted that there was little fat, sugar or vitamins in the meals and they only barely got 2,000 calories a day, though many of the inmates there were growing teenage and young adult boys.

Early every morning a man would come around selling coffee and rolls, which Leopold and Loeb occasionally purchased. They could also buy snacks during the day, which they also sometimes did.

Joe Stein’s Restaurant

66 W Austin Ave

In the early 1910s, Skelly’s Restaurant was next to the courthouse on 66 W Austin Ave (which today is Hubbard Ave) and owned by Joseph A. Skelly. The criminal court building took up a full block, and the restaurant was across an alley from the building. In the photos above you can see the Skelly sign and the proximity to the Criminal Court Building (the one with the large, rough hewn stone walls).

Then in the late 1910s that restaurant was taken over by Joe Stein.

While his restaurant did good business both with shoppers and businessmen in the area as well as reporters, police, lawyers, witnesses and others who had their offices in the criminal court building, Stein became further ingrained into the jail as well. Because most of those being held in the Cook County jail hadn’t been tried yet, they still maintained a certain amount of rights they wouldn’t have if sent to prison, and one of those was the right to eat what they pleased. As mentioned in the 1922 Cook County Jail Survey: “[Inmates] are subjected to a jail diet that is monotonous and repellent; from which they find escape, if they have the money, in food purchased from a private restauranteur operating in the jail.”

Stein came to an agreement with the Warden, in that if prisoners wanted to purchase food rather than eat what the jail provided for them, almost all of them would buy through Stein. Part of it was convenience: him being only an alley away, and another part was security. Food from outside restaurants would have to be searched, and parts of it would have to be removed to conform with the jail’s rules. That, and it would be easy to sneak poison or a weapon into the food. Through the partnership with Stein, there was a trust that no contraband would come through his meals. This worked well for both parties, one Chicago Tribune article reporting that Stein sold 25-50 meals per day to inmates of the Cook County Jail.

Though Leopold and Loeb of course didn’t see it during that summer, the interior of Stein’s restaurant was often described by others. Stein lined the walls of his restaurant with photos of famous lawyers and criminals, many of them signed. Several of the men on his walls had been fed by Stein, and he always provided last meals (typically chicken) to men about to be executed free of charge. Discussing the reason why, Stein told a reporter in 1925: “I get a real pleasure out of [my hobby] because I’m usually the only one to visit a condemned man on his last day. Relatives seldom come. And even the most hardened criminals thank me when I bring them food.”

Stein’s restaurant was also described in the book Paradies Amerika by Egon Erwin Kisch: A Dr. Becker was coming to attend to the hanging of David Shanks, but the execution was called off and he went to the restaurant next door to have a coffee. When he sat down, Mr. Stein greeted him and introduced himself as the owner, and the supplier of fried chicken last meals to the men executed next door. On the walls of a niche in the restaurant hung pictures of these dead, dying and condemned men he had served. He pointed to various photos, telling stories about them, including Russell Scott, who he supplied a last meal to four times as he went through a series of appeals, before Scott hanged himself.

June 1

Leopold recalled his first, less than stellar impression of Stein’s meals in his autobiography:

[Around 5pm] “We were told to sit on a long wooden bench facing the tiers of cells, and presently one of the prisoners-a “trusty,” I guess-brought us each a somewhat soggy cardboard picnic plate, covered on top with another cardboard plate. That one was less soggy. In between, as investigation showed, was food. A steak, some potatoes, and some squishy sliced tomatoes, all jumbled together and all somewhat the worse for wear. Presently the trusty returned, brining us each a large metal soup spoon. I sat and waited; I thought he’d be back with the rest of the silverware. I was to learn.

When no more utensils arrived, I took another look at the food. It wasn’t very appetizing-looking, and this was no time to be eating supper anyhow. Way too early. I wasn’t hungry. And I didn’t know how to go about attacking the meal-the steak especially-with just a spoon. I solved the problem by giving the plate away to the first prisoner who passed. He was a seedy-looking old character, about sixty, who fitted exactly my fiction-derived notion of a “wino.” Maybe he was one. He grabbed the plate gratefully and gobbled the food in a hurry. Lack of utensils was no problem to him. It wasn’t to me either, after a day or two.”

June 2

As we get into this murky territory where all I have to go on are what the newspapers claimed Leopold and Loeb ate, it’ll become clear quickly that they were likely far from accurate. Often different papers would claim they ate different things for the same meals, sometimes even the same paper would trip up and include those kinds of contradictions within the same article. The reporters were likely getting this information from the jail guards or making it up themselves, so while this may give an idea of what kinds of food they were able to get and how they were eating, it shouldn’t be taken at face value.

On June 2nd, newspapers reported that a relative of either Leopold or Loeb left $50 at Stein’s for credit and gave orders to “see that Leopold and Loeb get the best in eats while in jail.” The quote itself was very likely made up, but the families did establish credit with Stein so they could pay for the teenagers meals for the summer.

June 3

According to the Hearst papers, this morning Loeb was quoted as telling a guard: “I’m going to have breakfast brought in.” The guard allegedly replied: “Not allowed. You are not permitted to have food brought in until after you have been examined by the health physician. You had better try this, for you will not be examined before 9 o’clock.”

Both went without the jail breakfast and instead got a delayed breakfast from Joe Stein’s restaurant, of bacon and eggs, cereal and coffee after their appointment with the doctor. Another paper claimed that they didn’t get the Stein breakfast, and instead went hungry until lunch time.

The Chicago Herald-Examiner reported that Leopold and Loeb ordered the following:

Lunch: breaded prok chops, fried potatoes, sliced tomatoes, radishes, bread, butter, apple pie and coffee, with cigars.

Dinner: fried spring chicken, French fried potatoes, rhubarb pie, bread and butter, apples and coffee, with cigarettes.

June 4

This morning after being woken up at 6:30, both declined the jail breakfast, though they did make purchases from the ‘walking store,’ one newspaper reporting that they both purchased coffee and rolls, another that Leopold bought a doughnut and coffee and Loeb a piece of coffee cake.

At 8am it was reported that their Stein breakfasts arrived: ham and eggs, toast, French doughnuts, oranges and American fried potatoes.

June 5

According to the Chicago Daily Journal the pair had bacon, eggs, buttered toast, apples, oranges, coffee and rolls delivered from Stein’s.

According to the Hearst papers, reporters interviewed Leopold and Loeb’s cellmates, and both commented on the catering. Thomas, Leopold’s cell mate said “When he offered me half his chicken yesterday, I knew he was right.” Loeb’s cellmate Bill Donker, was quoted as saying: “He gave me some ham and eggs this morning. I wonder if he’ll have a breakfast like that every day.”

June 6

According to the Philadelphia Inquirer, Loeb ate the jail breakfast, while Leopold sent out for all meals.

June 8

According to the Chicago Herald-Examiner, Leopold and Loeb had a breakfast of chicken and rice with coffee, which both shared with their cellmates.

June 9

According to the Chicago Daily Journal, today they had jail breakfast as well as things from store and Stein: bacon, potatoes, coffee, toast, cigarettes. The paper also claimed that every day since they’ve been in they’ve had fried chicken. But the Hearst papers disagreed: saying that at lunch Loeb got some jail food, but soon decided not to eat it, and apologized to the attendant.

June 11

According to the Chicago Daily Journal, they both passed up the jail breakfast for Stein’s.

June 12

A Chicago Herald-Examiner reporter described Loeb as eating with a healthy appetite. “He patronizes the jail chuck wagon, has meals sent in from outside and usually saves part of his dinner to eat later at night.”

June 14

According to the Chicago Daily News, Leopold and Loeb were denied breakfast today, as they would be having a specific physical examination with the defense psychiatrists. The psychiatric examinations lasted a month, from mid-June to mid-July, and though they sometimes had to skip breakfast before tests, Leopold enjoyed the examinations for the unique culinary benefits they brought, as he explained in a draft of his autobiography:

“There were dividends connected with the psychiatric examinations other than the information we obtained. For we generally did not return to our cells for the noon meal. Usually dinner was sent up from Joe Stein’s restaurant for the doctors and ourselves and we ate with them. This meant that we could order what we wanted, that it would be served hot, on regular china plates, that therefore could be gravy and sauces. And there were knives and forks to eat with, instead of monotonous, silly soupspoons, which were our only utensils in our cells.”

June 15

The Chicago Herald-Examiner reported that they had lamb chops, vegetables and apples for dinner.

June 17

According to the psych reports, Loeb was given no breakfast this morning, as he was undergoing a blood sugar test.

July 4

According to the Chicago Tribune, they got a chicken dinner.

July 24

According to the Philadelphia Inquirer, at noon recess, Leopold and Loeb talked with their brothers and asked them to bring candy for them to eat in jail.

July 29

Reporter Tyrell Krum claimed he spent a day with the defendants in jail, and described all of their meals. When he first arrived:

Krum: “Well, Babe, how goes it?”

Leopold: “Couldn’t be better. Gee, but the weather looks great out there.”

Loeb: “Up, Babe?”

Leopold: “Yes, sir. How’s the breakfast?”

They got their packages that were left in front of their cells and ate.

When lunch recess came they dashed for their cells, Leopold: “Come on over here and have dinner with me.” Krum sat on a bench outside his cell, he pushed a plate of liver, onions, potatoes, radishes, onions, tomatoes and bread. “Sorry we have no knives or forks to give you. Against the rules, you know, have to use your fingers.” The meal was soon over, and the remaining food was cast on the floor for further disposition.

July 31

On this day the Chicago Evening Post gave an overview of their meals and attitudes towards food. Note that this is the only mention I’ve seen of Stein’s closing or them having their own cook on Sundays:

“Their meals are brought to them three times a day from a good restaurant in North Clark street just around the corner from the Criminal court building. On Sundays, when the café in question is closed, the boys have their own special cook, a woman domestic, who comes to the jail and prepares their meals for them. They are not, however, extremely hearty eaters, according to the restaurant man who supplies their food. Their chief articles of hot weather diet appear to be watermelon and cantaloupe. The cantaloupe frequently a la mode.

If they do not eat heavily, they eat often. Leopold sometimes has tea served in his cell immediately following the adjournment of court at 4 o’clock, and a friendly screw (jailguard) not infrequently scoots out at 10 or 11 p.m. for a late evening collation. Breakfast is usually taken comparatively late, between 7 and 8 o’clock…Loeb’s breakfast generally is a heartier one than that of Leopold. The latter is rather “picayunish” in his taste and prefers a breakfast of the lady-finger variety.”

This morning, according to several newspapers, Loeb asked Allan for candy and cookies to be sent to him during the morning recess in court.

August 1

According to the Chicago American, Allan Loeb talked to a reporter today and said: “Dickie is cheerful today, of course, but he was disappointed not to get the stick candy and cookies he asked me to send him. I sent them, all right, and must inquire why he didn’t receive them.”

August 28

According to the Chicago American, when the defendants went back to jail after the conclusion of the hearing “lunch awaited them and they ate ravenously.”

“Well, it’s over,” sang out a reporter.

“Well, it’s over, all right,” said Nathan Leopold Jr., munching on cookies. “At least the trial broke up the monotony of jail life a bit.”

“Please go away and let me eat,” said Dickie with a laugh.

September 10

(before court)

The Chicago Evening Post reported that they got three eggs, sausage, fried potatoes, toast, peaches and cream, coffee and chewing gum for breakfast.

The United Press wire service reported that they took coffee from prison cart at 6:30, and ordered out for breakfast: sliced peaches, fried eggs, pork sausage, fried potatoes, toast, cookies and chewing gum.

The Chicago Daily Journal reported that they got the same breakfast of sausages, eggs, potatoes, toast, cookies and sliced peaches brought by Stein employee Florence Bette.

(after court)

Many papers reported about Leopold and Loeb ordering a meal after they were sentenced, the Chicago American relaying the following:

“Go out and order us a big meal. Get us two steaks-“ Leopold beaming, indicated 3 inches with his hands. “And be sure they’re smothered with onions.”

“And bring every side dish that you can, as this may be our last good meal. And bring chocolate eclairs for dessert.”

And the Chicago Evening Post:

Leopold: “Go out and get us two big juicy steaks. And get us all the nifty side dishes you can. This is probably the last real meal we’re going to get for a long, long time.”

Loeb: “And say, get me a chocolate éclair, if you can.”

Joe Stein commented on this order in the Chicago Daily Journal: “The biggest order I ever got,” said Stein. “They wanted friend chicken and caviar and lots of other stuff I didn’t have. So I  sent them big beefsteaks smothered in onions and pie and cake and lots of fruit. I’m sorry they’re going; they’re the best customers I ever had.” The paper noted that they also received a package of cigarettes each, as they did every meal.

Leopold described this in a draft of his autobiography: “Dick and I took the opportunity of ordering our favorite meals from Joe Stein’s restaurant across Dearborn Street; we knew that it would be some time before we were eating steak and chicken again.”

September 11

According to the Chicago American, for breakfast each ordered four eggs, double orders of toast, fruit, cookies and coffee and cigs. Loeb after finishing For lunch they ordered chicken and French fries but got steaks smothered in onions, pie, milk, cigars and cigarettes.

According to the Chicago Evening Post they asked to put in a double order of bacon and eggs, three hard boiled eggs, five pieces of toast, sliced peaches and coffee. Their usual packet of cigarettes came as well.

According to the Belvidere Daily Republican they put in a “double order of everything” for breakfast.

When recalling the summer of 1924, Joe Stein told a reporter: “They ate nearly everything. Leopold, especially, was a heavy eater. He gained 14 pounds during those four months.” He may have been misremembering here, as Loeb gained 18 pounds in jail, while Leopold gained only 2.

Stein follow-up

In 1929 the Criminal Court Building moved to its new home on South California Avenue, and it was reported that Stein and his restaurant would move along with them, but it wasn’t to be. In June the Chicago Tribune reported that when an inmate was executed in the new location: “Walter Freeman, chef in the jury quarters, had supplied the traditional last meal of chicken and trimmings. Formerly the meal was sent in gratis by Joe Stein, who kept a restaurant near the old jail.” Perhaps ill health was what kept Stein from following the court: as he died on August 19, 1930, at only 49 years old, leaving behind a wife and two children.

Other restaurants they may have dined at:

Madison Park Hotel

Leopold and Loeb’s friend Richard Rubel lived here with his family, and it’s very likely they would dine here with him sometimes. In 1920 it was reported that “the restaurant is located on the east side of the lobby, facing the boulevard, and will seat 250. A $1.00 table d’hote dinner is featured,” and here is a typical menu:

For more information on Chicago’s dining scene during this time see:

Edgewater Beach Hotel Salad Book (1926)

Dining in Chicago by John Drury (1931)