The four buildings that comprise the Makawao Crossroads have a common tie: the name Tam. It was natural that the Chinese, the first ethnic group brought in for plantation labor would be early residents and property owners. Tam Sing, Tam Chow, Tam Yau, Tam Ching, Tam Apo, Apo Liilii, Tam See, Tam Wah Chan, and Tam Tin Fook, all from the village of Sam Chow, were bound together through business partnerships and marriage before the turn of the 20th century. At one time, Chinese merchant families owned all four corners of the Makawao Crossroads. Later immigrant groups joined the Chinese as residents and merchants in Makawao.
Pineapple started in the Makawao area after the turn of the 20th century at a number of ranches and small properties. In 1926 Libby, McNeill & Libby began planting in Makawao along with the newly established pineapple division of Haleakalā Ranch and Maui Agricultural Company. The two companies merged to form Maui Pineapple Company. The pineapple workers lived in the town itself and in outlying areas. Makawao town served as both the commercial and social center for workers.