Before they invaded Astoria in 2234, the Raider gang that would later become the Crossguards were known as the Gutrippers, a large band of extraordinarily savage and bloodthirsty maniacs pillaging all along the west coast. A couple of months before they came across Astoria, however, a new leader had fought his way to the top. Unlike most others in his gang, this leader, a man called "Short" John Silver, was cunning and intelligent, while also charismatic and brutal enough to keep the rest of the Gutrippers under his command for more than a few weeks, which was the usual expiration time of a Gutripper gang leader. Where most other Raiders saw a place to pillage when they reached Astoria, John saw opportunity. Thus, they established themselves in the city and started to live off of terrorising the inhabitants instead of simply razing the place to the ground.
Through John's sheer force of will and his relentless punishment of insubordination within the ranks, the Gutrippers slowly but surely began to reform into an organised structure, showing an actual semblance of discipline. As the years passed by and Short John Silver eventually passed away, however, the presence of the gang in the city started taking its toll on the population as well as on the gang members themselves. Their size was slowly but surely diminishing, and their grip on the city was loosening, while the previously well-preserved city started to dilapidate under decades of misuse.
In the second half of the 23rd century, a man called Elias came into power. He saw that the Gutrippers were no longer capable of sustaining themselves as regular Raiders, so he reformed the gang into an entirely different form of organisation: a mob syndicate. The newly-christened "Crossguards" retreated their presence to the bridge of the Columbia River, where they could demand toll from whomever wanted to cross over it. Though this was met with a fair amount of resistance within the Gutrippers, Elias' right hand man, a colossal, savage brute ironically called Angel, was quick to curb any rebellious sentiments, and thus the Gutripper gang was ushered into a new era of prosperity, acting as a barely civilised extortion syndicate.
- The gang's original leader, Short John Silver, is a not-so-subtle reference to the fictional pirate captain Long John Silver from Treasure Island. Both led and organised a vicious gang of outlaws through great cunning and strength of wit.