The history of Kaiwiki Sugar Company begins in the 1860s when the sugar industry was young and sugar production was more an individual effort than a corporate venture. J.M. Lydgate, who grew up in Hilo, traced Kaiwiki’s history to one of four small plantations extending northward from Hilo. In 1869 a real estate transaction showed that the Ookala Sugar Co. purchased 8,679 acres for $15,500 to establish a plantation. The new owner was Judge F. H. Harris with General William H. Soper as the president and manager.
In 1872 Ookala had 650 acres planted to cane and 175 laborers were employed. Ownership changed in 1875 when the Hitchcock Brothers purchased the Ookala plantation for $15,000. In 1879 Ookala was chartered with a capital of $100,000 represented by 100 shares at $1,000 each. Under the new charter, Hackfeld & Co. served as the new agent and W. L. Green, the new president. Several changes in agents followed: from 1878 to 1884, G. W. Macfarlane & Co.; from 1885 to 1887, W. G. Irwin; from 1888 to 1889, J. N. Wright; from 1890 to 1902, W. G. Walker; and from 1903 to 1909, C. Brewer & Co.

Although Ookala Sugar Company owned a total of 8,679 acres, its cane land was limited to 1,405 in fee simple and 3,005 acres of leased land. Located between the Hamakua district and the rain- drenched lands of the Hilo district, the land rose to an elevation of 1,800 feet, with steep slopes and a frontage on the sea of about 4 ½ miles and a depth of 2 ½ miles. Because of its adverse natural location, both irrigation and fluming were impossible and the plantation depended entirely on natural rainfall. Thirteen great gulches divided the Ookala fields making the land subject to erosion and transporting the cane to the mill was a major problem. Although the soil supported good crops of cane, the plantation was not profitable. In 1909 bankruptcy was finally declared, and the controlling interest passed to Theo. H. Davies & Co., the Honolulu agents. The defunct Ookala Sugar Company was renamed Kaiwiki Sugar Company.
Growing sugar under adverse natural conditions did not, however, dampen the new Kaiwiki management. The steep slopes and the thirteen great gulches became challenges. In 1910 Kaiwiki increased its annual yield to 2,134 tons and by 1932, the first million ton year of Hawaii sugar production, Kaiwiki Sugar produced 12,1389 tons.
Increased production came about as a result of modern scientific methods of agriculture and milling. For example, until 1913 planting was almost restricted to the Yellow Caledonia variety of cane, but with the introduction of the D-1135 seedling which was better suited to the higher fields, the Yellow Caledonia cane was confined to the lower areas. In addition, a short railway system extending along the lower fields transported the cane to the mill. For the higher fields, a five-mile wire rope system was used to carry the cane downhill by gravity in sling loads to be dropped into rail cars for mill delivery. Sacked sugar from the mill was delivered to Hilo Railroad Company for shipping. Since steam plows were too heavy to transport from one field to another across the gulches, mules were used for plowing. In 1914 water for the mill and all domestic use was piped three miles from Kaawailii Gulch.
In 1920 Kaiwiki Sugar Company produced 5,939 tons of sugar and about 600 laborers were employed. Improvements included a clubhouse, cottages for single men, and a tennis court.
Corollary to Kaiwiki’s mechanization program in the 1930s, the company also improved its skilled labor force. Manager Leslie Wishard sought capable Hawaii-born workmen and mechanics, paid them high wages, and provided them with modern houses and above-average surroundings. A new water and sewer system was built for the plantation camps, including hot water in all the houses. In addition, fully equipped boarding houses provided community kitchens, dining rooms, and the company hired first-class cooks.
The company also maintained a small but well-equipped hospital with a staff of registered and visiting nurses who held daily clinics in all the plantation villages. A baseball field and grandstand were constructed for the sports aficionados and an old hall was converted into a modern air-conditioned 300-seat talkie theater where Waikiki first-run pictures were shown three weeks after they were seen in Honolulu.
In 1939 the aerial cable form of cane transportation was being discontinued and the crop of 1940 was the first in which all the cane was trucked directly to the mill. Also in 1940, a new mill yard cane derrick was installed as were new boilers in the mill. Kaiwiki Sugar Company not only became one of the three lowest-cost plantations in the territory; it also gained the distinction of being the first plantation to mechanize its entire crop operations.