It is not for nothing that Jack Rackman is most commonly known as “Plaid Jack.”
Though he owns a wardrobe frankly immense in its scope, said wardrobe consists almost exclusively of conflicting patterns of plaid. This has generally been a source of bewilderment (and several unsubstantiated reports of temporary blindness) to the other members of the Brotherhood of the Coasts.
The current leading theory among the Brotherhood is that this is intended to give him a strategic advantage in battle, inflicting sensory overload upon his enemies and perhaps even driving their feeble mortal minds to madness.
The exact effectiveness of such a strategy remains debated.
He would, however, still likely be a famous pirate even without his famous fashion sense.
Despite his relative youth and the brevity of his career, Plaid Jack has become one of the standout members of this generation of the Brotherhood of the Coasts. So much so, in fact, that his fellow pirates recently elected him to stand as the Speaker for the Brotherhood’s annual General Assembly.
While not the youngest ever elected to the position, Plaid Jack is the youngest Speaker elected by the Brotherhood in a very long time.
Although Plaid Jack is an accomplished fighter, sailor, and naval commander, his greatest victories have been won in the diplomatic arena. Intelligent, charismatic, and magnanimous, Plaid Jack has a gift for making friends and making other people make friends.
Amid the large personalities and short tempers of the Brotherhood of the Coasts, this is a decided asset and has allowed him to diffuse several nascent conflicts within the Brotherhood.
In addition to being lauded as one of the Brotherhood’s foremost diplomats, Plaid Jack is regarded as either famous or infamous as one of the Brotherhood’s most prolific ladies’ men.
He is variably admired (primarily by the young men in the Brotherhood) or scorned (primarily by the women of the Brotherhood) for this habit.
Plaid Jack has thus far demonstrated an uncanny ability to keep his numerous girlfriends and sweethearts hidden from his other girlfriends and sweethearts.
This, despite the fact that he and his many, many lover affairs are an ongoing inspiration for humourous songs and the punchlines of off-colour jokes among the members of the Brotherhood.