[2][3][4] He attended Dartmouth College, and on a dare, he jumped into a vat of starch that had frozen over during winter, which led to severe pneumonia.

[3] In Los Angeles, while working in the fruit fields, he started a small delivery company that soon became responsible for also delivering many of the city's morning newspapers, which put him in contact with the publisher of the Los Angeles Times, Harrison Gray Otis, who liked the entrepreneurial young man and hired him as the Times’ general manager.

As a community builder and large-scale real estate speculator, he became arguably the leading citizen of Los Angeles in the first half of the 20th century.

Chandler was directly involved with helping to found the following: the Los Angeles Coliseum (and bringing the 1932 Summer Olympics to L.A.), the Biltmore Hotel, the Douglas Aircraft Company, the Hollywood Bowl, The Ambassador Hotel, the California Institute of Technology (Caltech), the Automobile Club of Southern California, KHJ radio station, Trans World Airlines, the San Pedro Harbor, the Los Angeles Athletic Club, the California Club, The Pacific Electric Cars, the Los Angeles Art Association, the Santa Anita Park racetrack, the Los Angeles Steamship Company, the Ahwahnee Hotel in Yosemite National Park, and the restoration of downtown's Olvera Street.

[5] As a real estate investor, he was a partner in syndicates that owned and developed much of the San Fernando Valley and the Hollywood Hills (Hollywoodland).

Magdalena, whom Harry called "May," died at age 29 of puerperal fever two weeks after Alice May's birth on August 4, 1892.

Sixty-one years later, the Caltech Board of Trustees voted in 2021 to have Chandler's name removed from the building for his involvement with the Human Betterment Foundation.