The team was originally formed in 1885 at the Argyle Hotel, a summer resort in Babylon, New York. The team was so skilled in the game, and achieved victory over so many of the nearby amateur "white" teams that they attracted the attention of a promoter, Walter Cook. To appeal to a broader audience, Cook styled them the "Cuban Giants", although there were rarely (if ever) any Cubans on the Cuban Giants. The team remained one of the premier Negro league teams for nearly 20 years.
The team went on to become the "world colored champions" of 1887 and 1888, and spawned imitators.
There are two different tales on how the Cuban Giants got their start. According to Sol White, a player who would join the Cuban Giants several years after they got started, Frank P. Thompson, a headwaiter at the Argyle Hotel in Babylon, Long Island, would regularly play baseball with the other waiters that soon became an attraction for the hotel's guests. Before long, he signed three star players from the semi-pro black team, the Philadelphia Orions, and the team went on the road to contend any team who would play them.
However, according to an interview with Thompson himself published on October 15, 1887, in the "New York Age", an African-American newspaper, the majority of the ballplayers did not come from the hotel's staff, but from several other black teams. In Philadelphia, Frank P. Thompson organized the Keystone Athletics in May 1885, and in July they were transferred to Babylon, L.I. By August the Athletics had partnered with the Manhattans from Washington, D.C., and the Philadelphia Orions, and it was the coming together of these three teams that created the Cuban Giants. Walter Cook from Trenton, New Jersey was their white owner and Stanislaus Kostka Govern was their black manager.
Govern, who was a native of St. Croix, Virgin Islands, understood how a team could financially prosper in the Caribbean at this time. His own team, the Manhattans, had been playing in Cuba since 1882. Thompson had a connection to Henry Flagler through Osborn D. Seavey, and once the team was through with their Cuban winter tour, they came to St. Augustine, Florida, to entertain the guests at the newly forming resort hub.
The Cuban Giants would come back to Florida many times during their existence. During the St. Augustine years, Thompson put together an organization called the Progressive Association of the United States. Thompson was the president of the Association, and Govern acted as secretary. Thompson used his position to conduct annual sermons for the Cuban Giants and any citizens who wanted, to come together against prejudice in the South. These sermons were widely well received and inspired others to join him in the cause.
In 1886, Walter E. Simpson bought the team and gave them a home at the Chambersburg Grounds in Trenton, New Jersey. Two months later, he would sell the team to Walter I. Cook.
Cook came from a wealthy family and was generous to the team with his money, especially when it came to illness or injuries, and he is known as the Giant's most well-liked owner. They even played a benefit game for him in which they donated their pay to him. J.M. Bright purchased the Cuban Giants from Cook in June 1887. Bright was able to get them into the Middle States League in 1889, as joining a league was something the team had been trying to do for some time. However, Bright was not nearly as well-liked as Cook, and had to deal often with renegade players. This would be the team's last year in Trenton. In 1890 the entire team fled and played as the Colored Monarchs of York, Pennsylvania. In 1891, the heart of the team fled to their rival, Ambrose Davis’ Gorhams of New York City, then called the Big Gorhams.
This dismantling and reassembling of the team became routine year after year until 1896, when E.B. Lamar Jr. from Brooklyn bought the team from Bright, renaming them the Cuban X-Giants. Bright responded by putting together an inferior team calling them the "Genuine Cuban Giants" or the "Original Cuban Giants". The Cuban X-Giants had a successful ten-year run as one of the best black teams in the East.