Losing strategy
Captain 1 decides to attack at 22:00. He sends his sailor out with the message (22:00 attack) to deliver to Captain 2. Upon arrival, Captain 2 reads the message, notes the time of the attack, and sends a message that also says 22:00 attack. He sends the sailor on to share the message with Captain 3. However, we have a problem. Captain 3 is a traitor. He wants the attack to fail. So, when he gets the message, he rips it up and replaces it with a new message that says 21:00 attack (9 PM). The sailor continues unaware. Captain 4 now receives a message saying 21:00 attack. He notes the time, signs the message saying 21:00 attack and sends this on to Captain 5, who then sends the same message to Captain 6. Now, the message has gone around everyone, but we have a problem. The dishonest captain has disrupted the result. We now have three captains (4, 5, and 6) with 150 warriors attacking the pirate ship at 21:00. Expecting others to join them, they instead get outnumbered and overpowered by the 200 pirates. The victorious pirates now stream out of the pirate ship and join forces with the treacherous Captain 3. Suddenly, the two remaining captains (1 and 2) have only 100 warriors and find themselves fighting 200 pirates plus 50 traitors. Unfortunately, the pirates and traitors win.