Nov. 19, 1904 Nathan Freudenthal Leopold is born in Chicago, Illinois, to Nathan and Florence Leopold (née Foreman), a wealthy immigrant Jewish family from Germany.
June 11, 1905 Richard Albert Loeb is born on in Chicago, Illinois.  He was the second of four sons born to Albert and Anna Loeb.
Sept. 19, 1909 Robert "Bobby" Franks is born to Jacob and Flora Franks.
1917 At age 12, Richard Loeb enters the innovative University High School, adjacent to the University of Chicago campus.
ca. 1920 At age 15, while attending the Harvard School for Boys, Nathan Leopold becomes acquainted with Richard Loeb, who was attending the University of Chicago as a freshman.
1921 Florence Leopold, Nathan Leopold's mother, dies.
1921 - 1922 Both Leopold and Loeb transfer to the University of Michigan at Ann Arbor, where they room together until Richard movs into the Zeta Beta Tau fraternity house.
Nov. 1923 Nathan Leopold and Richard Loeb begin plotting to commit the "perfect murder."
May 20, 1924 Leopold and Loeb prepare for the kidnapping and murder.  They bind a chisel with tape, buy rope and hydrochloric acid, obtain ether, hip boots and gags from the Leopold house, and Leopold writes the jointly-composed ransom notes on his Underwood portable typewriter.
May 21, 1924 At about 5:00 p.m., Bobby Franks is kidnapped and murdered by Nathan Leopold and Richard Loeb.
May 22, 1924 The body of Bobby Franks is discovered by Tony Minke, a Polish immigrant railroad worker.  A pair of eyeglasses are found near the body.  Morticians initially assumed the glasses belonged to Franks, and placed them on the body.  However, the boy's father would say that the glasses did not belong to Bobby, who had perfect eyesignt and never wore glasses.

The glasses were ultimately traced to Nathan Leopold.
May 25, 1924 At about 2:00 a.m., Loeb uses pliers to pry the keys from the Underwood typewriter used to type the ransom notes.  The keys are placed into a small bundle, and the bundle, along with the typewriter and its case, are thrown off the bridge at Jackson Park.

Later that morning, Nathan Leopold, Jr. is 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."
May 29, 1924 Nathan Leopold is picked up and brought into State Attorney Robert Crowe's office for further interrogation.
May 30, 1924 In the early morning, Nathan Leopold is again brought into State Attorney Robert Crowe's office for questioning by Crowe and Chief of Detectives Michael Hughes.

His partner in the crime, Richard Loeb, is also interrogated.
ca. May 31, 1924 Detectives question the Leopold family's chauffeur, Sven Englund, who lived in the family's garage.  When asked about Leopold's car, Englund and his wife confirmed that it had been in the garage all day on May 21, the day of the murder.

When confronted with Englund's statement, Richard Loeb demanded to speak with Crowe and District Attorney John Sbarbaro, and began confessing the true story of the murder.  When told that Loeb was confessing, Nathan Leopold also confessed that they had rented a Willys Knight car and kidnapped and murdered Bobby Franks.
June 1-2, 1924 While housed in separate rooms at the Windermere Hotel on 56th and Hyde Park Blvd., Leopold and Loeb lead detectives around the south side of Chicago.  They would point out where they had disposed of Franks's clothes, as well as the typewriter used in the ransom note, a second machine owned by Leopold, which he had dumped into the Jackson Park lagoon after the murder.
ca. June 5, 1924 Divers find the typewriter in the Jackson Park lagoon.
July 21, 1924 The first day of trial.
Aug. 22, 1924 Defense attorney Clarence Darrow delivers his closing arguments to the jury.  He had convinced the Leopold and Loeb families to enter a plea of guilty, and his powerful summation -- which some have called the finest of his career - would ultimately result in the avoidance of the death penalty for the killers.
Sept. 10, 1924 Nathan Leopold and Richard Loeb are each sentenced to life terms plus 99 years for the kidnapping and murder of Bobby Franks.
Oct. 1924 Nathan Leopold, Sr., sells the home at 4754 Greenwood and moves to Lakeview, living at 420 Roscoe Street, near Belmont Harbor.
1927 Nathan Leopold, Sr., married Mrs. Daisy K. Hahn of Los Angeles.
April 5, 1929 Nathan Leopold, Sr., dies.
Jan. 28, 1936 At age 30, Richard Loeb is murdered in Stateville Prison, Joliet, Illinois, by a fellow prisoner who claimed Loeb had made homosexual advances toward him.
1958 Nathan Leopold is released from prison on parole.
Late 1960s The Leopold mansion at 4754 Greenwood is destroyed.
Aug. 21, 1971 Nathan Leopold dies in Puerto Rico, of heart trouble brought on by his diabetes.