John Ernest “Jack” Pickering (1877 - 1933)
Jack Pickering was born in Wales and grew up in Surrey where his father owned a large horse-breeding farm. He was in the livery business in England before he came to North America. He came to Dawson around 1900 and started an express service. He and Rilla Hay Siebel were married in Dawson in 1908. Pickering applied for a Bonded Carrier permit in 1909.1) The Greenfield & Pickering Stables on Third Ave and Princess Street in Dawson had the only seven-passenger touring car for rent in the Klondike in August 1913. They also had livery horses, saddle horses, and the only rubber-cushion tired buggies. They made a specialty of catering to touring parties.2)
In 1915, Pickering and Jim Greenfield were taking wood and freight contracts around Dawson. They formed Yukon Silver-Lead Mining in 1919 with a mine on Mount Haldane in the Mayo District.3) Pickering staked the Pinocle claim in 1919 and the company hauled ore for Keno Hill Ltd. from the Silver King Mine to the sternwheeler landing at Mayo.4)
The Whitehorse-Dawson mail contract was awarded to Greenfield and Pickering in 1925.5) They took over the Mayo-Dawson mail contract from Coates & Kastner when motorised transport took over the ore haul.6) They purchased the equipment from O.F. Kastner and prepared to deliver a winter mail service. Greenfield was in charge in Whitehorse and Angus McInyre was at Dawson.7)
In 1926, Greenfield and Pickering won the Royal Mail Contract to carry mail and freight between Whitehorse, Dawson, and Mayo. This was a weekly service with four-horse outfits and sixteen stopping places: Takhini, Little River, Braeburn, Montague, Carmacks, Yukon Crossing, Minto, Pelly Crossing, Summit Roadhouse, Junction Roadhouse (at the Mayo Road junction), Stewart Crossing, McQuesten, Strychnine Lake, Flat Creek, Hollenbecks Roadhouse, and Fournier's Roadhouse. Greenfield operated the Whitehorse end and Angus McIntire, who had the Keno Hill ore haul for the company, manned the Dawson end. Pickering was the trouble shooter.8)
Klondike Airways was operated by Greenfield and Pickering Royal Mail Service after the failure of Yukon Airways. A Whitehorse lawyer, Phelps flew mail on behalf of Greenfield and Pickering. The company used a de Havilland DH-60X Cirrus Moth, G-CAUM, as well as Treadwell-Yukon Company's FC-2W2, G-CARM registered to Willard L. Phelps, who also owned the Moth and provided his equipment to Klondike Airways. Klondike Airways described only one aspect of the service provided by the company and did not denote ownership of the aircraft. In February 1928, Pickering announced that if the company's winter mail contract was extended for four years then the company would purchase two airplanes and operate them when business and weather allowed (during breakup and freeze-up). The airplanes were never purchased, and arrangements were made with Treadwell Yukon to lease one of their planes. In October 1928, a notice in the Dawson Weekly News announced that scheduled and passenger flights between Dawson, Mayo, and Whitehorse would commence immediately. Klondike Airways was authorized to fly the mail north from Whitehorse in October 1928 and Tommy Stevens’ was the first official airmail flight in the DH-60 Moth “Rilla-Martha” G-CAUM from Whitehorse to Mayo, Keno, Wernecke, and likely Dawson. Greenfield and Pickering lost the contract and terminated their Overland Trail operations in 1929. On 12 February 1930, a second company, also called Klondike Airways under the directorship of TC Richards and WL Phelps, continued the arrangement initiated by Greenfield and Pickering. Jack Pickering died in California.9)