While this was not Bolokoth's first adventure, this certainly would not be his last. While on his travels, he decided to stop at Bree, and it was in the Prancing Pony that he met him. A man of an appearance and culture that Bolokoth had instantly recognized as an Easterling.
He had discovered the man to be Zalspahro, a man with as many weapons and fancy armour as his beard was cared for and his charm was great. He seemed to love to use this charm on everyone he met, especially women. Bolokoth actually met him as he was using his charm on a woman he called Nar-yees. Bolokoth joined the conversation and together the two almost overwhelmed the ladies at the the table. During the conversation however, Bolokoth was sure to hint at the man that he knew about Easterlings and perhaps knew a thing or two about him.
It was after the ladies had left that Zalspahro put aside his charm and got down to serious business, wanting to know how Bolokoth had come to know this much. After informing him that he brought no ill will towards him and had journeyed in the east before, Zalspahro began to tell Bolokoth more, with the threat of death if crossed. He was a new and uprising crime lord with wishes to bring together the most elite of the brigands, criminals, and warriors to begin a new life.
After he had told Bolokoth this, he added that now that he knew of all this, it would be most likely a better idea to remain quiet about it, or else. Bolokoth, deciding this would be a chance at a kind of adventure that would not turn up again, seized the opportunity to not only just "remain quiet", but to be employed by Zalspahro.
Time had passed, and while there were not any large adventures, there were times to look back onto. Zalspahro wasn't like any of the other crime lords, he did not hide in the Chetwood and have a group of brigands do his work for him. He walked directly into Bree and roamed the town without fear.
He even got himself into a bit of a... disagreement and in the end, knocked a woman unconscious by butting his forehead onto hers right in the middle of the marketplace. That resulted in him being thrown into Bree jail with a five-hundred gold bail on his head.
Bolokoth however had seen the event and went inside with the act of being his older brother from Gondor and the him having went ahead and spending all of his coin on ale and getting himself drunk. He found Zalspahro using his "charm" on his guard, offering her the chance to spend the night in his cell with him and enjoy herself. With the pretense of taking him out of Bree, and five-hundred wooden gold coins, Bolokoth easily was able to "escort" Zalspahro out of bree, even with the watch realizing they had fooled and chasing after them.
It was from this moment on that Bolokoth stopped viewing Zalspahro as an employer, but as a friend and one of his kin. With any other crime lord, it would have been foolish, but as Bolokoth was not like other men, Zalspahro was not like other crime lords.
