Kaptin Bluddflagg is an Ork Warboss from Dawn of War II and the main character of the Ork campaign- unlike many other Ork Warbosses, he is a mercenary of sorts who while always ready for a bit of mindless violence is also happy to make and break deals as required to get what he wants.
As a Freebooter Ork, he lives the life of a space-pirate and his primary concern is loot, pillaging and similar "work" - rather than conquest.
History
Dawn of War II: Retribution
Long before the events of this game, Kaptin Bluddflagg has made a living in the Aurelian sub-sector, acting as raider and (on occasion) mercenary-for-hire to the petty lords that held dominion over the area.
His crew easily numbered in the hundreds, allowing for effective campaigns that often saw the Freebooter rich. However, his greatest happiness was his Kill Kroozer- a colossal space ship that he used to raid every planet within reach.
Crash Landing on Typhon
Unfortunately for Bluddflagg, his life of relative ease wasn't meant to last. Sub-sector Aurelia had been stuck in a near-endless battle for the past 10 years and the Imperium of Man's leaders- the High Lords of Terra -decreed that the sector was to be cleansed by Exterminatus, effectively destroying every planet and killing every last living creature within the area.
One group, however- the Blood Ravens, a Space Marine Chapter -couldn't allow this to happen. They knew that their own Chapter Master and Chief Librarian, Azariah Kyras, had been the source of the corruption not just in the sector, but through the entire chapter. Whilst civil war broke out between corrupted and loyalist Space Marines, one of the latter- Captain Gabriel Angelos of the 3rd Company -asked Imperial Inquisitor Adrastia to halt the Exterminatus. As she was an Inquisitor, she could marshal any and all forces in the name of saving Mankind. Unfortunately, this included Bluddflagg and his crew.
At the time, however, Bluddflagg was blissfully unaware of what was coming. He and his crew had just gone through a Warp jump when (unbeknownst to them) the Imperium shot their ship out of the sky, causing it to crash on Typhon, a jungle planet just below. The crash took several lives, leaving only four survivors from the crew- Bluddflagg, Mister Nailbrain (his first mate and Mekboy- an engineer), young master Spookums (a Kommando) and Brikkfist (a dimwitted Stormboy). Bluddflagg and Nailbrain were still getting their heads to stop aching when a pack of Eldar attacked them. Figuring they were the ones who shot them down, Bluddflagg went after them, picking up crew members on the way and bringing the local Feral Orks to heel.
Eventually, Bluddflagg tracked down the Eldar leader and killed her. His forces, however, were far from finished with the fight. Adrastia offered Bluddflagg a deal- kill Kyras, and she would give him a good fight (which meant three Imperial Guard regiments to kill and a battlefield of his choosing). However, after Bluddflagg was denied the Inquisitor's hat- which Bluddflagg grew interested in -he decided to abandon the contract in favor of killing Eldar. This ended when Adrastia revealed who really shot down his ship; enraged, Bluddflagg accepted the contract, but warned the Inquisitor that she would pay for her actions.
Hunting for Tellyportas
With his ship wrecked, Bluddflagg had to take a more land-locked form of transportation- tellyporta arrays. The nearest one sat in temple ruins nearby; unfortunately, a band of rouge Imperial Guard troopers had taken over. Complicating matters further was the fact that their leader had command of a Baneblade- a super-heavy tank with enough firepower to break an entire army with ease. What followed was a dangerous game of hide-and-seek, where Bluddflagg and his crew had to break cogitators to send local automated turrets into a frenzy, leaving them to shoot the Imperial Guard.
Eventually, Bluddflagg found the first array. With no test subjects available, the Orks had to use themselves. Thankfully, it worked. Their next stop- Calderis, a desert world and recruitment center for the Blood Ravens.
Looting Calderis
Getting to Calderis was easy; unfortunately, leaving wasn't simple. The corrupted Blood Ravens, led by Sargent Lysandros, were purging Argus- the capital city of the area. While the Orks loved destruction, forgetting to take any loot was ridiculous. The Orks were quick to arrive, cobbling together some vehicles to aid in smashing the Blood Ravens and their firebase. The battle went smoothly and the Orks were all the richer.
Before leaving, however, the Freebooters fought against their own kind- an Ork WAAAGH!!! led by Warboss Smashface. The Warboss, sick of how the WAAGH!!! that had been forged there remained stuck to just one planet- one that was quickly loosing people to fight -had decided to move his WAAAGH!!! to another world, perhaps even to the whole sub-sector. In order to do this, he had a massive Ork convoy send truckloads of gear, weapons and other necessities to a launchpad where an Ork rocket had been put together. However, the Warboss knew something could go wrong, so he ordered his men to drive over "shiny bridges", believing that they brought good luck. Kaptin Bluddflagg overheard the entire transmission and broke the bridges, forcing the WAAAGH!!! into a bottleneck, where Bluddflagg's crew attacked and destroyed the convoy. So horrid was the battle, so vicious was the fight that Smashface deemed it necessary to confront these upstarts; the Warboss didn't survive, but all of his surviving warriors fell in-step with Bluddflagg.
Kyras' "Test-Stomp"
The next world on the journey was Aurelia- the former capital of the Aurelian sub-sector. Long ago having been frozen by a shift in orbit and a Warp Storm, the planet was left an icy wasteland. However, some Chaos Space Marines had made a base there, managing to create a portal into the Warp. While the presence of such fiends hardly phased the Kaptin, he knew these Chaos Space Marines would be good test subjects for his battle against Kyras.