After the demise of Whitehead Aircraft Ltd. in 1919, Whitehead sought to transform the aircraft works into a car manufacturing facility for large mass production of Whitehead Motor cars. This Flight Global magazine article from February 19th, 1920, suggests that bureaucracy was the obstacle in bringing this enterprise to fruition. However, an article from Flight Global Magazine, dated November 4th, 1920, shows that this bureaucracy was likely related to Whitehead being owed money by the Government, which was not forthcoming. He had obviously made plans to settle his debts and start a new business. Without the necessary funding, this would not have been possible.
Other enterprises included a chicken farming business, but the chickens quickly fell sick and died.
The next venture was a building business in Twickenham. Many houses were built, some of which are apparently still standing today. The building business began to fail and soon enough, Whitehead once again declared bankruptcy owing over 25,000 pounds sterling.
The Monte Carlo/Newborough Club, established in 1928, was Whitehead's next brainchild, which was started in his own large house, Cross Deep Lodge, Twickenham, which he moved into in 1925. An orchestra played nightly, as patrons participated in gambling and watched the cabarets. A police raid in 1929 or 1930 ended all of this when Whitehead's establishment was found guilty of allowing people to drink alcohol after hours. Cross Deep Lodge became a nursing home in 1930, until it was demolished in 1965.
Cross Deep Lodge
Given unpaid debts and multiple bankruptcies, Whitehead owed large amounts of money. This debt was settled by his father, which would not be the last time.