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At the age of three he moved with his family to Santa Cruz, California, where he was educated in the public schools. After studying in his father's office, he attended Cooper Medical Institute for two years, and in 1883 he graduated from the Hospital College of Medicine at Louisville, Kentucky.
Following graduation, Dr. Bailey came to Kahului, Maui, to join his father who was in practice there. Upon his father's departure in July, 1884, the younger Bailey continued to practice in Kahului and succeeded his father as government physician for the Makawao District.
Dr. Bailey married Miss Mollie Nelson of New Hampshire sometime in 1883. Four years later she died (probably late in December, 1887), leaving a baby daughter.
In April, 1888, Dr. Bailey left for Santa Cruz but returned to Maui in December of the same year to settle his business affairs. Leaving the Islands for the last time in the spring of 1889, he settled in Santa Cruz where he was in practice until his death.
Dr. Bailey died in Santa Cruz on August 24, 1897.
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