Later that year, McIntosh thought it was time to develop the more artistic side of his entrepreneurial genius. One morning, Sydneysiders awoke and learned with amazement that Hugh D. McIntosh had paid £100,000 to take over the huge Rickards theatre circuit.
For a brief while he ran both establishments, but on December 2nd 1912, the Stadium was taken over on approval by Reginald (Snowy) L. Baker. In March 1913, he bought the business lock, stock and barrel and Hugh D. McIntosh ceased to have any but sentimental interest in the great stadium he had created.
McIntosh began to live the role of the successful tycoon, buying a mansion, "Bellhaven," at Bellevue Hill and a fleet of Pierce-Arrow cars with his crest prominently displayed on the doors. A personal friend of the Premier, W.A. Holman, he was elected to a seat in the NSW Legislative Council, which he held till he was made bankrupt in 1932.
Hugh D. entertained on a fabulous scale. Many visiting celebrities, enjoyed his hospitality. He made his money easily and he squandered it the same way. His gifts of motor cars to friends, diamond studded wrist watches to chorus girls and gold cigarette cases to mere acquaintances, became the talk of the town.
Hankering for fresh fields, McIntosh now bought the Sydney Sunday Times the oldest Sunday newspaper in Australia. It was a vehicle he would later use to persecute the great Les Darcy.
McIntosh had his own ideas on how to increase circulation. One such example was an offer to a notorious murderer named Simpson on the eve of his execution. Simpson would be paid £5000, if he would endeavour to come back from the dead and appear at the Sunday Times office before witnesses.
Visited in his cell, Simpson accepted the proposition eagerly. He jotted down the address of the newspaper office, so he would not "get lost on the way," and promised to do his best to solve "the age old riddle of whether the dead could return."
Forty people gathered in McIntosh's office on the night following Simpson's execution. Simpson, however, was not one of them.
By such stunts, McIntosh did more harm than good to the paper, which had previously enjoyed a valuable prestige. It became one of his financial failures.
In 1928 Hugh D. McIntosh tried his luck in England. He bought Broome Park, a seventeenth century mansion set in 600 acres and formerly owned by Lord Kitchener. In association with C.B. Cochran, he promoted a few fights in the Olympia Annex in London and also at stadiums in Paris.
None of them earned enough to keep him in cigars. For four years, McIntosh lived a fantastic round of pleasure in England. He poured out his money entertaining the rich, the famous, the titled, and beggared himself in the process.
In 1932 he returned to Australia broke. Bankruptcy proceedings were instituted against him. His liabilities were proved at a staggering figure. But Hugh D. McIntosh could not be kept down for long. He was soon staging a comeback, promoting fights at the Sydney Stadium.
Full of enthusiasm, he imported the American heavyweight Young Stribling and matched him with the Australian heavyweight Ambrose Palmer, hoping to repeat his 1908 clean up with Burns and Johnson. It was not to be. The takings amounted to only £3800 and Stribling alone had been guaranteed £3000.
Another financial body blow followed with the failure of a boomed match between Ron Richards and Fred Henneberry. The now aging promoter was down - but he was not out.
He threw himself into the flotation of a chain of cake shops and opened a large guest house in the Blue Mountains.In 1935 he sailed once more for England, where on August 1 he opened what was to be the first of a chain of 500 McIntosh milk bars throughout the country.
With an excess of ballyhoo, a company was floated which McIntosh said would soon be disposing of the milk output of a million cows, to two million customers a week.
McIntosh opened a dozen milk bars in London, and it seemed he was on the right foot again. However, lack of capital and cut-throat competition beat him.
When he died in 1942, he was penniless. His old time friends had to contribute to a fund to defray his funeral expenses.