Rolen

After the 50 Year Time Skip
When coming back to G-Rash Bay, Rolen found himself at a loss as of what to do. Having traveled with his companions aboard the Ship called Wanda, he was uncertain as to where to go moving forward except for retuning to the Shadowfell. Having finally obtained the means for extra planar travel, the new commodore Blagg Baldreks snatched it away from him. Frustrated, Rolen was near ready to challenge Blagg to a fight to the death when he recieved an offer that surprised even him. "You're not fucking going anywhere yet, so why not join the navy formally? I've known you're worth enough to be an admiral," Blagg said with the kind of confidence only a man without fear could. Famous last words.
Invigorated by his new sense of power, Blagg made one of the worst decisions in his life. While he was starting his own happy family, Rolen was sleeping his way through the bay, leaving behind broken hearts and many lovers with mysterious accidents. Some so broken hearted, they left town and were never seen again, and many so emotionally broken they lost the ability to speak. While certainly not the brightest man in the world, Rolen was well aware that Blagg had begun to refine the policing of the bay. While he was always a host to various criminals and privateers, Blagg was trying to make the bay a better place and needless to say, Rolen was harming that effort. After 25 years of close watch, Rolen disappeared. Blagg felt a mixed sense of anger and relief knowing the biggest asshole he had ever had the displeasure of working with was finally out of his life. That was, of course until the day of black death. 
The Day of Black Death
3 years after Rolen 'disappeared', a fleet of some of the navy's finest ships were decimated by inky black tentacles that arose from the sea as a group of hooded fanatics murdered any surviving men on board before sinking with the ships as the tentacles disappeared. Blagg was no stranger to the strange aberrations and the tentacles were intently familiar. There was no question that Rolen was behind this. After a second attack, a cultist was captured and questioned. After a day of torture, the only information they received was that the Tendrils of Rolen would not stop amassing until the bay was his. Pissed, Blagg kept the prisoner and began to send out his bravest men to stop the cultists. The next morning, the captured cultist was found insane in his cell. A spell Blagg new well, the feeble minded cultist was strangely incurable, setting a new panic amongst the bay.
The Truth of Rolen's Past 
As a warlock, Rolen worshipped one of the great old ones, but as the Eldritch horrors go, it is not always clear which being it is who gives you their power. As he became more and more powerful through the years, Rolen became more aware of how he obtained his powers. As he learned that he had been part of what may be an infinite time loop, it was when he fathered himself he learned that he had been deeply connected the dark, sentient star Hadar. During his return to the Shadowfell, Rolen found himself profoundly lost in the mysterious dark landscape as he made pilgrimage to discover where he came from. Feeding off of the negative energies for over 1 millennium, Rolen became insanely powerful through partially his own skill, but more in his deepening connection with Hadar. In time, he became what is known as a Star Spawn. Being truly devout, he gained a cult of followers. Within another century, he met a woman who resembled the beauty he had met on the sentient planet. He impregnated her only to realize that the son she had given birth to was in fact himself. It was at that moment, he truly began to descend into madness. 
Back to the Bay
Upon realizing he was his own father, Rolen found an invigorated sense of immortality. He could not die. Should he be killed he was now alive again elsewhere to circle through ages of unknown life and power. Being mad with power, he returned to G-Rash bay finding just in time to see himself leaving for the Shadowfell. He quickly began to start a cult on the material plane claiming (and truly believing) himself to be one of the great old ones. He would spend days going back intime, and starting other cults and spreading his darkness (often times, making sure his followers left idols or portraits of himself in his vanity) but somehow always landing back at the bay just at the time he left. Those who were faithful to him were given a piece of his power as an avatar he could channel Hadar's greater powers and became a warlock patron. Those who opposed him soon found themselves falling into a great madness, which was executed through the feeble mind spell, though sometimes when his power is directly graced by Hadar himself, even a greater restoration spell cannot fix the broken mind (or so it seems, as the spell was cast multiple times on a person for eventual success in some case though many find it easier to give up on the person affected). 
Going back and forth in time strengthening himself and his power eventually led to a huge attack on G-Rash bay, decimating part of their Naval forces known to the locals as the Day of Black Death where he and his fanatics destroyed several naval fleets. Successfully completing one of his goals in life which was to be powerful to fuck with Commodore Blagg Baldrek. A few years after the causing problems for the bay, he came across the naval commander Ulysses Reginald Debussy Mal'shakar, almost getting him to join his cause and bring in the most powerful pirate group in G-Rash bay before he escaped and was captured by the G-Rash Bay naval force for piracy and obstruction of justice. Whether or not Rolen will seek revenge seems unknown now, as there are other ways he can continue his growth as the worlds largest thorn in Blagg's side.