He moved on to selling shoes at a retail store and arrived in Seattle in 1898 to handle the estate of his uncle, John H. Nagle.

Dilling's real estate investments in Seattle prospered during the Klondike Gold Rush, making him among the wealthiest men in the city.

Dilling was elected by a large margin,[3] carried by the first female electorate in the city's history and the support of the Public Welfare League,[4] and began sweeping reforms to undo many of Gill's controversial decisions.

[5] Dilling served out the rest of Gill's term and declined to run for re-election in March 1912, endorsing George F. Cotterill.

[6] Dilling Way, a one-block street near City Hall Park and the King County Courthouse in Pioneer Square, is named in the mayor's honor.