Julian Armstrong had been commissioned by the Evanston Yacht Club to find out if it was feasible to find either a floating or ashore clubhouse at the drainage canal after it was decided that Evanston Harbor was no longer usable. In the summer of 1920 he purchased an old "turn of the century" lumber schooner named "Petrel" for use as a floating clubhouse in Wilmette Harbor without consulting other members. After a rather stormy meeting of the Board of Directors it was decided that the cost would be more than most of the members could afford so they rejected Armstrong's plan.
Since Armstrong had already purchased the estimated 70 foot long old sailing ship, he decided to go ahead on his own and organize a new yacht club. With the aid of Edwin Clark, a yachtsman and architect (who was the architect of the Winnetka Village Hall and Highcrest School in Wilmette), the boat was rerigged as a "pirate ship" called "Port of Missing Men". It was first towed into Wilmette Harbor in May 1921 (one year before Sheridan Shore Y.C. came into existence) as the home for the Buccaneers' Club. It was moored just off the north wall of the harbor near the present location of the Coast Guard Station.
The club had a major membership drive once their clubhouse was moored in the harbor. They had six one-design Cat boats built during 1921 which they used for racing. The Club President was Armstrong with Godfrey H. Atkin of Winnetka as Fleet Captain. Besides Atkin, John Burnham of Evanston and a few other members of the Evanston Y.C. joined the Buccaneers. By 1923 the fleet of Cat boats had grown to 15 and the Chicago Saddle & Cycle Club had bought fifteen similar boats which resulted in interclub racing. The Chicago Yacht Club 20 foot one-design fleet scheduled a few races from Belmont Harbor to the Buccaneers' Club during that year. According to the Chicago Post of April 27, 1923 members were planning to purchase "a good sized schooner yacht and enter her in the Chicago-Mackinac race". It also stated that "The club has been thoroughly overhauled, a kitchen and restaurant provided luncheons, and dinners will be served throughout the summer." Membership dues were $200 per year, a sizeable sum in those days.
The "clubhouse" was stored in South Chicago each winter and towed to what they called "Grosse Point Harbor" each spring, a major event of the season when members were invited to go along. As prohibition was in effect at this time, the club became noted for "wild parties" and evidently some of the wives forced their husbands to quit the club. By about 1926 the club was operating at a considerable loss.
The club made overtures to Sheridan Shore Yacht Club (snuggled down in the Marshal Mansion) to combine, but because of the large debts the Buccaneers had accumulated, Sheridan Shore rejected the offer. Interest died out and the "Port of Missing Men" was not even taken to winter anchorage but left in the harbor for the last few years. It sunk twice and had to be raised. The old boat was offered to the Sea Scouts but they refused because they did not have the financial resources to maintain it. Finally, it was towed to a point off Montrose Avenue in Chicago and on August 17, 1929 the hull was burned and then sunk to become part of the landfill for the new Outer Drive.