He was the publisher of the New York Herald, founded by his father, James Gordon Bennett Sr. (1795–1872), who emigrated from Scotland.

He sponsored explorers including Henry Morton Stanley's trip to Africa to find David Livingstone, and the ill-fated USS Jeannette attempt on the North Pole.

In 1867, under his father's tutelage, he founded The Evening Telegram, an entertainment and gossip paper[4] that later became the New York World-Telegram.

In 1872, he commissioned a Manhattan building design from Arthur D. Gilman, who popularized Second Empire and cast-iron facades.

[4] Bennett, like many of his social class, indulged in the "good life": yachts, opulent private railroad cars, and lavish mansions.

[5] In 1861, Bennett volunteered his newly built schooner yacht, Henrietta, for the U.S. Revenue Marine Service during the Civil War.

American expatriate artist Julius LeBlanc Stewart painted several works set on the yacht.

According to various accounts, he arrived late and drunk to a party at the May family mansion, then urinated into a fireplace (some say grand piano) in full view of his hosts.

He backed George W. De Long's voyage to the North Pole on the USS Jeannette via the Bering Strait.

The ill-fated expedition led to the deaths from starvation of DeLong and 19 of his crew, a tragedy that increased the paper's circulation.

The 2014 nonfiction book In The Kingdom of Ice written by historian Hampton Sides recounts the voyage and Bennett's role as a financier of the expedition.

and organized the first polo match in the United States at Dickel's Riding Academy at 39th Street and Fifth Avenue in New York.

The 1909 race in Reims, France was won by Glenn Curtiss for two circuits of a 10 km rectangular course at an average speed of 46.5 miles per hour (74.8 km/h).

From 1896 to 1914, the champion of Paris, USFSA football (soccer), received a trophy offered by Gordon Bennett.

After Sterling's death it was learned that he had appointed his long time intimate companion, Bloss, one of the executors.

[21] The Avenue Gordon Bennett in Paris, where the French Open's Stade de Roland Garros is sited is named after his father.