Nathaniel B. Raymond (b. 1855)
	
Nathaniel Raymond entered the Yukon over the Chilkoot Pass from Digby, Nova Scotia in 1899.((Jerry E. Green, //Yukon Riverboat Captains.// 2018 website: http://www.users.muohio.edu/greenje/)) Captain Raymond owned two small sternwheelers that were built in Whitehorse and operated on the Yukon River in the early 1900s. He was Master of the small sternwheeler //Clara// in 1900.((Jerry E. Green, //Yukon Riverboat Captains.// 2018 website: http://www.users.muohio.edu/greenje/))
	
Bill MacBride, the great authority on the Yukon riverboats, thought that Raymond’s steamer //Olive May// was sold and renamed the //Dora// in 1899.((W.D. McBride, "Saga of Famed Packets and other Steamboats of Mighty Yukon River." //Caribou & Northwest Digest,// Spring 1949: 100, 102.)) However, the //Olive May// continues to appear as an independent steamer owned by Raymond. In the early days of the gold rush, the //Olive May// competed with the Bennett Lake and Klondyke Navigation Company’s fleet of three small boats on the Tagish Lake run to Taku Landing and the connection to Atlin Lake.((Christine Frances Dickinson and Diane Solie Smith, //Atlin: The Story of British Columbia's Last Gold Rush.// Atlin Historical Society, 1995.)) Captain Raymond was registered as the Master of the //Olive May// in 1906.((Jerry E. Green, //Yukon Riverboat Captains.// 2018 website: http://www.users.muohio.edu/greenje/))
	
The little sternwheeler //Pauline// was built in Whitehorse for Captain Raymond in 1907. The //Pauline// was named for Pauline Raymond.((W.D. McBride, "Saga of Famed Packets and other Steamboats of Mighty Yukon River." //Caribou & Northwest Digest,// Spring 1949: 100, 102.)) After the //Pauline// was completed it went immediately to Dawson and in 1908 was doing a good business on Yukon River tributaries.((Royal North-West Mounted Police Annual Report. Sessional Paper No. 28. 1908: 16, 22.)) Raymond was listed as the captain of the //Pauline// in the //Polk’s Directory// of 1909-1910. In 1911, the //Pauline,// owned by Captain N. B. Raymond and his son John of Whitehorse, struck a rock near Big Salmon and, while delayed several hours while repairs were made, reached Dawson in good shape.(("Yukon River Disasters Very Numerous." //The Weekly Star// (Whitehorse), 26 May 1911.)) 

In 1912, the independent steamers //Vidette// and //Pauline// tried to operate after the middle of October but were frozen in at the Indian River.((Yukon Archives, Cor 722 (1912) WP&YR. RGI II-I)) During the Chisana gold rush in 1913, the //Vidette// arrived in Dawson from a trip eighty miles up the White River where she left the //Pauline// to relay the barge and freight to Donjek.(("Vidette Arrived." //Dawson Daily News// (Dawson), 19 August 1913.)) The //Pauline// was wrecked by running ice at Sunnydale Slough in Dawson in the spring of 1916.((W.D. McBride, "Saga of Famed Packets and other Steamboats of Mighty Yukon River." //Caribou & Northwest Digest,// Spring 1949: 100, 102.))