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In the late 1920s, in the important case Correa v. Waiakea Mill, Carlsmith represented the mill company, demonstrating that he had by then won the respect of his former "establishment" opponents. For the seven years that the case spent in the courts, son C. Wendell Carlsmith cut his legal teeth on the research. Because of this work, he became expert on sugar matters on the Big Island. His subsequent hire by the Hawaiian Sugar Planters' Association (HSPA) in 1934 changed the course of the firm's development.

Carl's two sons Wendell and Merrill, born in Hilo and educated at Stanford, joined him as full partners in 1932. Together the three created a solid client base, including much of sugar management that had dismissed the elder Carlsmith. Much of this was due to aggressive pursuit of the sugar industry. New Deal legislation designed to protect independent sugar growers opened the door for Wendell Carlsmith, then a 31-year-old unknown, the only lawyer in Hawaii who knew the sugar system intimately, to participate in writing new laws and regulations. He came to know personally the leaders of Hawaii's economy. The National Labor Relations Act, designed to protect workers from management, opened the door for mainland unions to start organizing sugar, pineapple and waterfront employees. This was Wendell's opportunity to become an "instant expert" on labor law, on more than one island.

Meanwhile, Merrill Carlsmith's bulldog litigation won case after case at home in Hilo. He also gradually took over the land law practice that had been his father's specialty.

As the elder Carlsmith aged and the two sons increased their management, a policy of creative expansion led to the foundation of a new firm structure at the end of World War II. When Carl Carlsmith retired in 1947, the firm was poised for renewed risk taking as the territory was poised for statehood. Territorial-era clients included Inter-Island Resorts, keystone of the firm's early expertise in resort development, Hawaii's largest industry. This was followed by Kapalua Land Company and other resort clients. For contracting and construction company Dillingham Corporation, another early client, Carlsmith lawyers were involved in many projects, notably the construction from scratch of the harbor of what was then the Emirate of Kuwait. For this international project, Wendell Carlsmith traveled to that Arab State, and also worked with the London firm of Freshfield's. Post-statehood the firm was increasingly active in land development, doing the legal work for the first condominium in Hawaii.

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