I recently retired my longest played character. It wasn't at the end of the campaign, only 3/5ths of the way through it, but his adventuring life was done.
Andrew Darkwell, a young Ulfen farmer from the Sandpoint region who 5 years ago was orphaned when a goblin raid destroyed his his families farmstead while he was out hunting one day.
He left for Magnimar where he met a young sailor named Kiirn. Kiirn introduced him to the commander of a mercenary company, and he spent the next 5 years learning war as a trade. After 5 years, he departed the company, with plans to make his own. He headed back home to Sandpoint, a big annual festival was about to take place there, and he was going to use that to springboard his plan. Hiring a few strong hands and adventurers in town, to include his old friend Kiirn who was now a Bard and had come to visit the festival himself, the village agreed to pay his band to patrol the roads before the festival, to make sure they stay safe for visitors who were travelling to Sandpoint.
From that point on The Rise of the Runelords campaign took place. He led the group of adventurers to avenge the goblin raids of the city, eventually conquering the stronghold at Thistletop. Following that, he convinced the mayor of the city to sign over land right of Thistletop and the Nettlewood to him. He was going to use it as the base for his new mercenary band. Shortly afterwards, Andrew was informed by the local ranger Shalelu that his whole family wasn't killed in the goblin raid those 5 years prior, but that his sister was taken, and sold as a slave to a band of pirates that operated from a base in the Marshfens, off to the south. The two departed (Andrew missed the 2nd book), and succesfully freed his sister, while bringing the pirates down. Shalelu had spent the two months they were together teaching him to become a ranger, and there were the beginnings of a romantic relationship starting as well.
They returned to Sandpoint just in time to meet Andrews old companions, travelling through on their way far to the east. The Lord-Mayor of Magnimar had sent the off to find out what had happened to an outpost of rangers who were responsible for securing Magnimars frontier border. Shalelu instantly said she would be joining them, and Andrew agreed to come as well. What followed was a couple months of fighting ogre hordes, freeing the last surviving members of the Black Arrows, the rangers mentioned, and learning that one was Shalelu's step father, and now the highest ranking member of the organization. It was here that he came into the possession of the bow of the previous leader of the Black Arrows, a powerful weapon that fired arrows that would explode with cold damage.
After some time, Andrew agreed to join the organization and help them rebuild. He would use his base at Thistletop to train new recruits to send out to the more dangerous frontier.
On the groups return to Sandpoint, Andrew hired a force of workers to begin building a new fortress on Thistletop, toppling the old goblin fort that was there, as well as a new Manor in Sandpoint, for his family to live in. Several weeks after their return, a giant raid took place on Sandpoint. Andrew led the cities defenses, and almost single handedly stopped the initial assualt cold by himself. When another attack came from a second direction, he sent the rest of the party off to deal with that, while he and his bow held the giants a the north wall at bay. After finally blunting that assault, he started to head back to join the others, and it was then that a Red Dragon joined the assault. It landed on top of a building that many of the towns people had taken refuge in, and began to set it on fire. Seeing that he had no time to wait for the others, he attacked the dragon alone, trying to draw it away from the citizens who stood no chance against it. A furious fight took place, his cold arrows causing grievous wounds to the dragon, but in the end, Andrew fell. The wounds he caused to the dragon forced it to flee though, and the rest of the party was able to fight off the giant force.
He was raised shortly afterwards. A couple of weeks was spent recouperating, both from the physical and mental trauma of being burned to death. He proposed to Shalelu in this time, but being an elf and he a human she was afraid of such a commitment, at the time. When he was physically ready, the group departed. Several of the townsfolk had been taken captive by the surviving giants of the raid. Shalelu stayed in the town this time, much to Andrews disconcert, but they departed. For some to rescue the prisoners, for Andrew, revenge.
They tracked the giants all the way to the Storval plateau. There they found a fortress that one giant named Mokmorian had built, gathering giant and ogre tribes preparing an army to attack the lands of man with. The group found a secret entrance through caves, penetrated the keep, rescued the prisoners, and defeated Mokmorian, cutting off the head of the army. Shortly afterwards the various tribes departed, most only under his banner because they were afraid of him.
With the return to Sandpoint, Andrew learned that Shalelu was pregnant. Between that, and his new found duties with the Black Arrows, he decided to retire. The wealth he had gained over the last several months ensured that his new family would be set for life. Through some political dealings with various nobles of Sandpoint, he found himself on a seat of the cities council,
In a years time, he had gone from penniless orphaned mercenary, to a famous adventurer, nobleman, and leader of a small army.
Artwork I had done to commemorate the character.