James Rolph, Jr., or “Sunny Jim,” as he was known, served more mayoral terms in San Francisco than anyone else. He was elected four times to office. These elections were not close, instead they were landslides in Rolph’s favor.
Young Rolph had many jobs growing up including newsboy, clerk, and messenger. Eventually, he started a shipping company with friends that allowed him to open his own bank. In addition to his career, his public persona was also greatly enhanced by all the work he did leading a 1906 Earthquake Relief Committee. All of this was just the foundation that eventually led him to run for public office and serve as mayor of San Francisco from 1912 – 1934 when he resigned the position to run and be elected as governor of San Francisco.
During his reign as mayor, he helped this great phoenix of a city rise from the ashes of the earthquake and grow strong. The civic center area was rebuilt, the International Exposition was held, and several infrastructure projects were accomplished.
His nickname, “Sunny Jim,” comes from that fat that he was a very jovial and personable character. He was known all over San Francisco as being generous and of good humor. He was a man who could talk to anyone about anything and make them feel comfortable and at ease. He was truly the “Mayor of All the People.” There is even a story of him inviting Communist demonstrators into his office in city hall for a visit, instead of ordering violence to be carried out against them like what was happening in other cities throughout the nation. You can’t get anymore San Francisco than that.
Never underestimate a person who is described as having “a great personality.”
Source: Historic San Francisco: A Concise History Guide, by Rand Richards. (I can’t recommend this book enough. It is awesome.)