Hillman was a real estate developer, and his business practices ranging into the fraudulent eventually landed him in a federal penitentiary.
[3][6][7] Hillman City resident Mikala Woodward, director of the Rainier Valley Historical Society, acknowledged at the time of the centennial of the neighborhood's annexation by Seattle, "We were named after a sleazy charlatan.
While never a serious challenger to Columbia City as the region's main business district, Hillman City did boast a real estate office, grocery, butcher, hardware store, bakery, tile factory, movie theater, and for a time an opera house and a circular fountain at the intersection of Rainier and Orcas.
However, with a near continuous facade of streetfront buildings and a modest pedestrian scale, Hillman City has the opportunity, many believe, to become an attractive neighborhood center.
[6] The Hillman City Business Association worked to improve the quality of life in the neighborhood, by organizing community events, patrols, and litter cleanups.