Wilson was superintendent of the water works and fire chief under King Kalākaua, and was Marshal of the Kingdom under Queen Liliʻuokalani.

He planned to land a ship of insurgents from Maui to attack Honolulu, but was the mission was aborted after the revolution was exposed and martial law was activated.

[4] Following World War II Wilson considered retirement he had been de facto leader of the Democratic Party of the original five founders only two remained.

Delbert E. Metzger was a Federal Judge and powerful Democrat but his judicial career reduced his participation in politics this left Wilson as leader.

But unlike his colleagues, Wilson himself an early Democrat and part-Hawaiian, allowed passage of 442nd veterans into the party, such as Daniel Inouye and Spark Matsunaga.

A damaging letter written by Wilson criticizing non-Hawaii-born Democrats alluding to Stainback was considered the major factor in his loss to Republican Neal Blaisdell.

During the late 1950s, Wilson advocated that the territorial government build a tunnel through the Koʻolau Mountains from Honolulu to Kaneohe through Kalihi Valley.

The city eventually proceeded with plans to build a second set of tunnels through Kalihi Valley, which opened in 1961, five years after Wilson's death.