A socialite without regular employment, Preston's father was described as a man that "had extravagant tastes, expended money lavishly and was without business employment", a fact which led his family to legal troubles. In 1899, while in Paris, Gwynne obtained a loan worth several thousand dollars from a jeweler. In February 1901, Gwynne transferred his interest in his property to his mother, Louise Gwynne. In the fall of 1901, the Paris money lender filed suit against Gwynne, for an unpaid loan of nearly $50,000 for diamonds. Shortly after his mother's death, in June 1902, Edward Gwynne filed a petition in bankruptcy, with liabilities of over $56,000 and assets of $57. Two years later, on May 10, 1904, Preston's father died of acute kidney problems at the age of 35, on the same day the case of the suit was to be brought up on the court. Preston was five years old at the time.