Retirement
Dempsey retired after this bout and made countless exhibition bouts. Dempsey's philanthropy was also noteworthy. In June 1932, Dempsey sponsored the "Ride of Champions" bucking horse event at Reno, Nevada. The Dempsey Trophy went to legendary bronc rider Pete Knight. In 1933, Dempsey was approached by Metro-Goldwyn-Mayer to play a boxer. The film, The Prizefighter and the Lady, directed by W. S. Van Dyke, co-starred Dempsey and Myrna Loy, and obtained good reviews.
In 1935, Dempsey opened Jack Dempsey's Broadway Restaurant in New York City's Times Square, which he kept open until 1974. Although closed today, many years later people still have fond memories of the legendary hangout. Dempsey was also an owner of the Colony Palms Hotel (then called the Howard Manor) in Palm Springs, California.
Dempsey divorced Taylor and in July 1933 married Broadway singer Hannah Williams, who had just divorced Roger Wolfe Kahn, and had two children with her. Shortly after Dempsey divorced Hannah Williams in 1943, the boxer married Deanna Piatelli and was married to her at the time of his death. Together with Deanna's daughter, Barbara, Dempsey would pen the book Dempsey later on in life.
When the United States entered World War II, Dempsey had an opportunity to refute any remaining criticism of his war record of two decades earlier. Dempsey joined the New York State Guard and was given a commission as a first lieutenant. Dempsey resigned that commission to accept a commission as a lieutenant in the Coast Guard Reserve. Dempsey reported for active duty in June 1942 at Coast Guard Training Station, Manhattan Beach, Brooklyn, New York, where he was assigned as "Director of Physical Education." Dempsey also made many personal appearances at fights, camps, hospitals and War Bond drives. Dempsey was promoted to lieutenant commander in December 1942 and commander in March 1944. In 1944, Dempsey was assigned to the transport USS Wakefield (AP-21). In 1945, Dempsey was on the attack transport USS Arthur Middleton (APA-25) for the invasion of Okinawa. Dempsey also spent time aboard the USS General William Mitchell (AP-114), where he spent time showing the crew sparring techniques. Dempsey was released from active duty in September 1945 and he was given an honorable discharge from the Coast Guard Reserve in 1952.
True to his passion for the sport, Dempsey wrote a book on boxing called Championship Fighting: Explosive Punching and Aggressive Defense, which was published in 1950. The book emphasizes knockout power derived from enabling fast motion from one's heavy bodyweight. Though no longer in print, Dempsey's book became and remains the recognized treatise in boxing and has influenced such works from Edwin Haislet and Bruce Lee.
Dempsey was also something of a cross-trainer; he wrestled in training camp and later took judo lessons. During World War II and while in the Coast Guard, he coauthored with Professional wrestler Bernard J. Cosneck, How to Fight Tough, which instructed Coast Gaurdsmen on close-quarters hand-to-hand combat incorporating boxing, wrestling and jiujitsu.
After the Louis-Schmeling fight, he expressed the opinion that he was glad he never had to face Joe Louis in the ring. When the Brown Bomber fell on hard financial times, Dempsey served as honorary chairman of a fund to assist him.
Dempsey made friends with Wills and Tunney after retirement and many books were written about his life. Dempsey even campaigned for Tunney's son John V. Tunney when he ran for the U.S. Senate, from California. One of Dempsey's best friends was Judge John Sirica, who presided over the Watergate trials.
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