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The Jolly Roger, 1929-1989
The Jolly Roger was constructed at 8721 Bothell Way (now Lake City Way) apparently shortly after Prohibition. Accounts differ, and some stories have it built as early as 1929, but the best assessment I have found throws doubt on its speakeasy history and track the construction date to 1934. For a brief time in 1935 it was renamed the Chinese Castle, then quickly renamed the Jolly Roger. It burned down under suspicious circumstances in 1989. The location is now a car lot across the street from Ying's Drive-In Chinese Food, which itself is in the former location of the Coon Chicken Inn
Whether or not the Jolly Roger was a speakeasy during Prohibition, the stories of illegal activities hardly stop at being a speakeasy -- it is also said to have had a long-running business in prostitution and illegal gambling.
Remarkable features of the Jolly Roger included the lookout tower, from which approaching police could be easily spotted from miles away given the remoteness of the area at the time, and a reportedly a series of tunnels through which patrons and workers could escape under the street and into the nearby ravines when the lookouts sounded the alarm.
Although no one was convicted of arson, the building was likely torched with the knowledge of the ex-owner, who was embroiled in a dispute with the current owner, and seen removing his possessions the day before the fire.
The building was named a Seattle Historic Landmark in 1979, but was demolished in January 1991 as preservationists were attempting to have it rebuilt.