Orlando Merchant, born on Feb. 12, 1856, was the third child born to George and Mary (Douglass) Merchant. As with many members of his family before, he became an active member of the fishing industry though primarily as a clerk and vessel owner. He married Charlotte Jane Gray (born Nov. 9, 1860) on Dec. 6, 1883. She was the daughter of William and Charlotte Burton (Johnson) Gray of Nova Scotia, and in 1876, when Charlotte was 16, her family moved to Gloucester.

In 1887, Orlando and Charlotte had a son, Roy Douglass Merchant (Jan. 19, 1887). This was their only child. When they first married they made their home at 41 Mt. Vernon and five years later moved to a house at 39 Mt. Vernon. These homes were both part of the area of Gloucester known as Eastern Point Hill. They lived here until Charlotte's death in 1909 from an embolism following an operation. Several years later, on Jan. 27, 1914, Orlando married a second time to Mary Garland Wonson (born Jun. 28, 1874). She was 39 and he was 57 at the time of this marriage. In celebration of this wedding, the Sch. Oriole was bedecked with numerous American flags as it was tied up at the end of the Wm. H. Jordan Wharf. Mary was the daughter of Addison and Mary (Averill) Wonson. This marriage produced another child on May 24, 1917, Miriam Wonson Merchant. The family continued to reside at the home at 39 Mt. Vernon.

As a child, Orlando attended school in Gloucester and after completing his education, he entered into the fish business when he joined then firm of Rowe and Jordan. Eventually, he became the confidential clerk to Mr. Jordan. Eventually, this firm was reorganized and continued business under the name of the William H. Jordan Company. In January of 1903, Mr. Jordan admitted Orlando as his partner in the shipping business. According to the 1979 recollections of a Mrs. Helen A. Tidman, an employee of the same firm (after Orlando had become a well-established member of the firm), Mr. Jordan rarely came to the office and Orlando Merchant handled all of the business affairs for the firm. The Wm. H. Jordan Company outfitted their fleet of fishing vessels, and had a variety of supplies (non-perishable food items, big rounds of cheese, barrels of pickles and crackers) needed for the long fishing trips. At the time of his second marriage, Orlando was serving as the treasurer of this firm.

During the time that he was employed Wm. H. Jordan, Orlando co-owned several vessels. He also operated some of these vessels under the name of Orlando Merchant & Company. Those vessels included the Esperanto (launched on Jun. 27, 1906 -- sunk on Jul. 25, 1921), the Clintonia (launched on Jun. 26, 1907 -- sold Nov. 1921 in Newfoundland), the Oriole (launched on Jun. 24, 1908 -- sunk on Aug. 12, 1916, after being rammed by a Norwegian steamer) and the Stilletto (launched on May 11, 1910 -- lost on Apr. 4, 1930 after she became stranded on a sandbar near Fork River, New Jersey). In addition to those mentioned, in 1911 Orlando listed as the owner of the following vessels: the Oliver Wendell Holmes (lost in 1903), the Harvard (built 1892), the Avalon, The Constellation, the Golden Rod, the Grayling, the Joseph Rowe, the Mary E. Harty, the Marguerite Haskins (built in 1893) the Harriet W. Babson, the Richard Wainright, the Henry M. Stanley, the Lewis H. Giles (built in 1893) and the Lottie G. Merchant (named after his wife, whom he always called Lottie).

The Sch. Clintonia became a part of a battle for continued government protection in 1909. In 1907, Orlando Merchant arranged to build identical schooners, both used the same designs and molds, and given the same name. One was built in Gloucester and the other in Nova Scotia. The Clintonia from Nova Scotia was able to provide fish at a much lower cost because they were putting less money into the building of the vessels ($9,400 for Nova Scotia vs $15,600 for the Gloucester schooner), less money into the fishing gear and providing a lower standard of living and provisions for the crews. Lumber purchased for the Gloucester vessels was also much more costly. Members of the Gloucester fishing industry, primarily represented by Thomas J. Carroll, President of the Gloucester Board of Trade (and General Manager of the Gorton-Pew Co.) petitioned the U.S. Government to maintain the current level of duty and protection so the Gloucester fishermen could remain competitive. Discussion of the vessels and costs continued through 1911, when Volume XXII of the journal, the Protectionist included an article about reciprocity and its advantages or disadvantages for the Gloucester fishing industry.

Besides being an active businessman, Orlando Merchant also contributed to the community in other ways. From 1910-1919 he was serving as the treasurer for the Gloucester Fisherman's Institute. This organization had been established in 1891 with the goal of improving the condition of fishermen and seamen.