Following his divorce in 1902, Shepard again returned to Paris, living at 244 rue de Rivoli. He made several more attempts as opening businesses, all of which were again unsuccessful. On April 27, 1905, Shepard knocked down and killed a 12-year-old girl, Madeline Marduel. A trial followed, and on October 26 the judge sentenced Shepard to three months imprisonment, a $120 fine and he was ordered to pay $4,000 in damages to the girl's parents. Shepard appealed the decision, and the case was eventually settled in January 1907, with a reduced sentence of six weeks imprisonment. After nine days in Fresnes prison, Shepard was pardoned after paying a further $2,000.
Racing
In the 1906 Vanderbilt Cup, a race started in 1904 by his cousin, William Kissam Vanderbilt II, Shepard lost control of his Hotchkiss HH car and hit two spectators who were killed in the incident. Unaware of what had happened, Shepard continued until reaching the service area at East Norwich. Here he was informed by his mechanic that his car may have collided with someone, and a telephone call to the race organisers confirmed what had happened. Upon hearing this, Shepard withdrew from the event. In 1907, Shepard was injured when he drove into a river in Monte Chiarl after a tire on his car became detached and sent the car bouncing over the bridge railing moving a further five yards into the river. He broke his collarbone with other slight injuries to his body.
World War I
During World War I, Shepard worked in a hospital for American volunteers for the French army in Chantilly, France. His work helped him to receive the Knight of the Legion de Honneur, the Croix de Guerre and the American Field Service Medal. He gave up his estate in Chantilly for those sick or wounded in the American Field Service. He served as president of the organization and chairman of its Paris Branch.
Personal life
On April 10, 1897, Shepard married Esther Potter, a 25-year-old widow, in a civic marriage. A religious ceremony followed at the insistence of Shepard's mother, after which the newlyweds left for Europe. Shepard went into business in Paris, but was unsuccessful. He briefly returned to the USA with his wife, but they separated and in August 1902, she filed for absolute divorce. Shepard later married Eleanor Leigh Terradell, daughter of Thomas Terradell. Her sister, Mercedes Terradell was married to Prof. Jean Labatut in 1929. During the War, they turned their home in Chantilly, France into a convalescence hospital. Shepard died on April 10, 1927 at his Miami beach estate, after a long illness.