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Reess Kairn was a Twi'lek member of the Jedi Order, having reached the rank of Jedi Knight, during the waning years of the Galactic Republic. On Ryloth, Kairn met a female with whom he fell in love, marrying her against the tenets of the Jedi Code and without the knowledge of the High Council. Keeping their love secret, Kairn remained an active Jedi, returning every so often to be with his wife.

On one occasion, Kairn returned to his home on Ryloth to find his mate with another man. Enraged, Kairn embraced his anger and killed both his wife and her lover before burning his home to the ground. Fearful of the punishment the High Council would seek against him, Kairn fled the Jedi Order and began a new life of space piracy. Establishing a pirate crew, Kairn sunk deeper into the grasp of the dark side of the Force and began raiding mines and trade ships throughout the Mid Rim.

His last known raid was on the planet Lorahns, where he ransacked the Great Temple of the Order of the Ffib, and killed four priests during his departure. Escaping with priceless artifacts, Kairn disbanded his crew as the darkness in his soul lifted. Seeking redemption, Kairn hired three Shi'ido to simulate his appearance so he could escape the Ffib Inquisitors. As the three Shi'ido dispersed across the galaxy, Kairn went to Balmorra where he subjected himself to transgenderative surgery to alter his appearance in both species and gender, to become a Human or Near-Human female. The results of the surgery were convincing, yet poorly done, and left Kairn with long lopsided scars across his face. He subsequently disguised himself as a blind priestess of the Order of the Ffib in honor of those he had killed.

To encourage the process of eliminating her doppelgangers, Kairn retreated to the Sanctuary Moon of Endor in 27 BBY and contracted the bounty hunter Aurra Sing to hunt down and kill "Reess Kairn". Claiming that the real Kairn had hired two Shi'ido to impersonate him, Kairn hoped that Sing would eliminate all three impersonators and believe that one was indeed the real Kairn. After Sing had traveled to Bespin, Hoth and Tatooine and killed each impersonator, she realized that she had been deceived and returned to Endor. While Kairn hired the Thranta Mercenaries to eliminate Sing should she discover the treachery, Sing appeared in Kairn's hut and shot her in the back of the head, killing her.