Another interesting part of Portland’s history is on the shadier side. In the late 1880s, Joseph "Bunco" Kelly, a hotelier, became famous for his side business: kidnapping young men and selling them to ship captains. Many of the hotel operators and bar owners in the area actually relied on this practice to supplement their incomes. But Kelly was the best at it. His practice involved intoxicating potential crewmembers by the dozen so he could deliver them to waiting ships. The men captured would wake up stranded at sea and be forced to work aboard the ships for indefinite periods of time.
Another interesting character in Portland's early history was "Sweet Mary," the proprietor of a brothel. She operated her brothel on a barge that went up and down the Willamette River. Her floating business was technically outside everyone's jurisdiction, allowing her to elude city laws and paying taxes.