On Sunday, May 25, 1924, Nathan Leopold, Jr. was brought to the State's Attorney's office for questioning.  He made a statement about his movements and his familiarity with Hegewisch swamp.  Later Leopold would tell Detective Gortland that he thought he'd be able to talk his way out of the situation, as he had on the 25th, and had he known "Loeb would peach," he would have killed himself and "taken a couple coppers out in the process."

Nathan Leopold, Jr. was picked up again for questioning on Thursday, May 29, 1924, and again on May 30.  The interrogation of Leopold took place over some 30 hours.

Richard Loeb was also questioned.  The statement was made Friday May 30, 1924, at 1:35 a.m.  The following people were present; Robert Crowe, Joseph Savage, Milton Smith, Michael Hughes, E. M. Allen, Samuel Ettelson and Nathan Leopold.

"Now Loeb," said Mr Crowe.  "You told me that Wednesday, you drove down town Wednesday, the 25th, [trial transcript indicates the 25th, actual date was 21st] you drove down town with this young fellow Leopold, in his car.  That is a sport model, it is a red car with a tan top, Willys-Knight?"

"Yes."

"You left the school around eleven o'clock or some time after eleven, between eleven and noon, that you had lunch at the grill room in Marshall Field's."

"Yes, sir."

"Yes or no?"

"Yes, sir."

"Then you went out to Lincoln Park?"

"Yes sir."

"And all the driving that you did that day was in this car?"

"Yes sir."

"You did not have a car yourself, did you?"

"No."

"You did not drive any that day?"

"No, sir."

"Have you got a car in your family that is a weather-beaten green?"

"Well, my mother has a Cadillac, yes, sir."

"A Cadillac.  And that is a sort of green?"

"Yes."

"Isn't it a fact that shortly after one o'clock PM you drove up in that Cadillac, you drove it and Leopold driving the red car drove the car to his garage and you saw the man that just went out, yes or no?"

"Yes."

"Who was he?"

"Pardon me, yes was to your question about had the man gone out." Loeb stammered.

"Who is he?" Crowe repeated.

"He is Leopold's chauffeur."

"Now isn't it a fact, Wednesday, May 21st, some time between one and a quarter after one you drove up to the garage, to Leopold's garage, you driving your mother's car, that green Cadillac, he driving the red car, and that he said to the chauffeur 'the brakes squeak so much here I want you to fix them'.  He says 'I can put some oil on them and you can use the emergency and if you are careful you will not run into anybody.' He said 'I would rather run into somebody than have that squeak,' and he turned the car over to the chauffeur and got into your car and drove away?"

"No."

"That is not a fact?"

"No."

"If the chauffeur says so he is a liar?"

"Yes."

"Although he has a particular reason for remembering?"

"It is not a fact."

"If the chauffeur took the car and oiled it up, oiled the brakes and fixed it up that would make the impression -- make an impression on his mind, would it not?"

"Yes."

"If he says that is a fact he is a liar or mistaken?"

"Yes."

"Then if he has an additional reason for remembering the particular day what would you say to that?"

"I would say he was still a liar or mistaken."

"Didn't you boys come back then somewhere around ten o'clock in the evening and take that red car out?"

"When is all this?"

"Wednesday, May 21st, the day this boy disappeared, that is not true?"

"No."

"The chauffeur is mistaken?"

"Yes."

"Do you and Leopold belong to the same fraternity?"

"No."

"You are not fraternity brothers?"

"No."

"Did I ask you last night about the letter he wrote you in which he said it would not do for cocksuckers to fall out?"

"Yes, sir."

"What significance do you attach to that?"

"The fact that he wanted to say, that a rumor had gotten around that he was a cock sucker."

"What difference would that make?"

"We did everything in our power to avoid any possible scandal in regard to that thing for two years, since it happened; that was three years ago, when this rumor started, and for two years we were very careful never to be alone together in public, seen together any place, or to be alone together any place where we could be seen.  We were careful so when we wanted to go to a theatre on a particular evening we would be careful to have somebody else come along, purely and simply on the advice of my brother who had told me to be careful and to – not see too much of Leopold, and if I did to be sure there was somebody else around."

"Wasn't that an intolerable condition to exist, two fellows that were very friendly and wanted to be together and could not be together without the world suspecting they were cocksuckers and you had to have a chaperon all the time?"

"No, it was not necessary."

"Wouldn't it be much better if you broke off, saying 'now listen, there is a lot of suspicion as to our relations here, you better go your way and I will go mine' and stop?  All this talk and let us forget it."

"We never did that, but for quite a while there we saw very little of each other.  It is just due to the fact that this here – that we were going to the University of Chicago and that we were together a great deal and that there was much more conversation."