In addition to owning and managing many of the largest circuses in the United States, he was also a rancher, a real estate developer and art collector.

At the same time that family management was evolving, the Ringlings were challenged by keeping two mammoth circuses touring during World War I. Manpower shortages, combined with railroad restrictions and the 1918 flu pandemic all contributed in the decision to merge the Ringling Bros World's Greatest Shows and the Barnum & Bailey Greatest Show on Earth at the end of the 1918 season.

[6] On October 8, 1918, the Ringling Bros. season concluded after performances in Waycross, Georgia, and the circus trains were routed to the Barnum & Bailey Winter Quarters in Bridgeport, Connecticut.

Although other family members had inherited stock in the company, as President he continued to manage the circus in the years prior to The Great Depression.

Ringling would bring the circus troupe across the river from Yonkers, New York, with acrobats and animals to entertain their guests at parties.

With the financial and personal difficulties that Ringling faced during the Great Depression, control of the property was lost and the house was ultimately demolished in November 1935.

The couple bought bay front property from Mary Louise and Charles N. Thompson, another circus manager who engaged several members of the Ringling family in land investments on the Florida Gulf Coast.

[14] After some 40 years in the entertainment business, along with his ownership of railroads, oil field and ranches John had become one of the richest men in the world.

[19] In 1933, the last of the Brothers Ringling, ill and aging John, who had owned more circuses than any other man on earth and whose fortune was once estimated to be $50,000,000, hobbled into a Federal Court in Brooklyn to testify on the loan that brought him low.

At a prize fight in 1929, Mr. Ringling related, he met William M. Greve, president of New York Investors, Inc. (realty), who agreed to lend him $1,700,000.

[32] Ringling was voted out of control of the business in 1932 by its board of directors and Sam Gumpertz was named vice president and general manager of the circus.

[38] Another of John's legacies is the Ringling College of Art and Design, which asked to adopt his name because of the cultural influence of the museum and its collection.

The Ringling Bros. and Barnum & Bailey Circus eventually closed after 146 years; in the face of weakening attendance, animal rights protests, and high operating costs, it performed its final show on May 21, 2017, at Nassau Veterans Memorial Coliseum.