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Wanamaker lady millinery expert and her trunks of samples from Palm Beach to Havana, Cuba for a fashion show.  On December 31st he competed for the 1919 Curtiss Marine Trophy by flying a repeated round-trip course between Palm Beach and Miami, covering 670 miles in a 3-passenger Curtiss flying boat.

At that time they were advertizing "Instruction and Passenger work, Charter Flights and Agents for Curtiss Products" and were rapidly building up a good business flying resort passengers from Palm Beach to Nassau, Bimini, Bahamas, Key West and Havana, Cuba, which was probably the first scheduled and advertized air line flying passengers from the United States to any foreign port.  Trans-Oceanic had hangars and shops at Palm Beach and ran flights on a regular schedule, with Early Birds George Page, Jr. and Clifford Webster also pilots for the firm.

In mid-February, 1920 McCulloch had a late day forced landing 30 miles at sea while returning with a party of five from the Bahamas.  He was flying a Navy type HS2-L flying boat with single Liberty engine and it was necessary to sit out the night afloat.  The next morning he was able to resume and flew into Vero Beach.  Operations returned to Port Washington, Long Island in the spring and in May he flew parties from Port Washington to Atlantic City, New Jersey to attend the Third Annual Pan-American Aeronautic Congress.  In June he carried parties to view the Yacht Races from the air while an Evening News reporter radioed his commentaries direct to the News office in New York.

In January, 1921 McCulloch looped a Seagull Curtis flying boat at Palm Beach before a large crowd, the first time this had ever been done.  During 1921 he did some test flying for aircraft firms and on August 16th broke the world 3-passenger flying boat altitude record flying the new Liberty-powered Loening Flying Yacht to 19,500 feet at Port Washington, Long Island.  His passengers were Grover Loening, Leroy Grumman and L. D'Orcy.

It is not known when McCulloch gave up flying, but apparently he continued to live in the New York area.  He later reportedly suffered a hunting accident in Canada and badly damaged one arm.  Following a long illness he passed away in a New York hospital in September 20th, 1955 at age 64, survived by his wife, three daughters, a son and a brother.

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