Tensions between the earliest incarnation of a Ruby Alliance; RAWR and Robertdonald originated with the incidents surrounding Cranberry IV in late 2004, regarding Robertdonald and Ridestowe's aggressions against Trans-Atlantic Empire. Robertdonald has already come into conflict with Silver Dawn during the blockade of Eta I, although it is debatable whether this was the start of the vendetta between the two factions, or merely a difference in playstyles causing a clash during colonisation. A clash in the forums between Avasta of Silver Dawn and RobertDonald continued to widen the rift between the two sides and the blockade of Eta by the alt flag Silver Dusk.  The conflict between the two groups came to light again in early 2005 as a dispute between Ptolemy and the flag of No Homers led to further conflict between NH and Carpe Nox.
The Scallywag War officially began when Carpe Noctem, Looterati, No Homers, and Silver Dawn publicly declared war against Robertdonald, and by extension his flag Scallywag Syndicate . Carpe Noctem and No Homers made the first moves by dropping war chests on Zeta and Endurance, islands held by close allies of the Syndicate, Lost Legacy and The Midnight Sun, respectively. The Ruby Alliance believed the flags holding Endurance and Zeta to be influenced heavily by Robertdonald, due to his holding of various key building deeds on both islands. With word ahead of time, the Syndicate was ready to blockade Jorvik and Luthien in return at the same time, dropping chests using the alt flag Scallywag Syndycate.
Both Jorvik and Endurance were hotly contested, with all of the blockades but Zeta being sinking. Endurance went the full 5 rounds with the intervention of Notorious Fandango. The coalition of the Ruby based flags moved their offensive forces rapidly between the four points of conflict, keeping smaller defensive forces at the two islands they were defending - Luthien and Jorvik. The main body of the Ruby Alliance began the day's conflicts at the Zeta blockade, securing a lead before switching attention to Jorvik, where the attackers were threatening to secure the first round of the fight. In a tense and exciting battle for both sides, the defenders pulled back from trailing to win the round. With the arrival of Notorious Fandango, eyes turned to the battle for Endurance. Fandango successfully won two rounds of the blockade but were unable to maintain their lead once the full force of the Ruby Alliance descended upon the island, edging out Fandango in a close battle by one round. The defenders, Midnight Sun, failed to win any rounds, and only returned the war declaration set by No Homers. By the end of the day the Syndicate's allies had lost both islands and had no gains to show for the all of the blockades, although the Syndicate itself still held their central stronghold of Cnossos.
With the loss of both Endurance and Zeta, the Syndicate then begin to prepare for the eventual attack on Cnossos, the only island left between them and their allies. Surprisingly, none of the flags that declared war attacked, but instead the Harbingers tried and were completely routed, failing to win a single round in an attack that was unrelated to the Ruby Alliance's campaign against Robertdonald.
The Cnossos Auction
With the realization that Cnossos island would hold their fleet in place and was a liability to them, the Syndicate then planned to give the island away in a raffle event.  By selling tickets at just 30k each, the flag was able to raise more then 1 million PoE for the eventual retaliation against those that attacked. Additionally, by relinquishing the rule of Cnossos, Scallywag Syndicate removed a potential target for the Ruby Alliance to strike them via. Strategically, in retrospect it proved a failure of the Ruby Alliance's battle plan not to target Cnossos; although it is debatable whether attacking the island would have been within the original principles of the plan, and the Ruby Alliance's perceived use of Lost Legacy and Midnight Sun as puppet flags by Robertdonald.
The original declaration of intent by the Ruby Alliance in March provoked speculations that the blockades were deliberately coincided to conflict with the March Madness familiar events, thereby distracting the attackers' opponents. The Ruby Alliance denied this was a deliberate strategic move. With a chance to finish all of the March Madness events, and a week to prepare the Syndicate attacked Jorvik on April 10th. In a hotly contested blockade the Syndicate walked away with the island after four rounds. Right after the island was taken, Robertdonald placed two shops, a tailor called Greenwolf Memorial Tailor and an apothecary named Blood and Oil. Also placed within the week was an ironmonger called Max Damage Inflictors and the weavery; Blood and Cloth along with a fifth shop.  The tailor was placed in a way that obstructed the bank somewhat and was soon moved, but it allowed them to only build one shop at a time. Even with that limit, they were still able to build four shops on the island in one week. This is believed to have led to the implementation of the existing OOO policy that only 2 shops can be placed in a week, an item that later came back to haunt them.