Monfreen was a planet on which there was a peninsula, where the mysterious Citadel of Shadows overlooked a whirlpool large enough to swallow a starship. The origins of the Citadel were unclear, but the place was a dark side nexus. Intrigued, a young Jedi named Ven-Mah Tyrrahl came to the planet and visited the Citadel. Long afterwards, as a 70-year old Jedi Master, at some point prior to the destruction of Ossus, Tyrrahl taught a praxeum of students on Monfreen, including the Padawans Lian Dray, Yeres Threem, and Cayli. Like his Master before him, Dray was also drawn to the Citadel, but failed his confrontation thither with the dark side. Seduced to its call, he returned to the praxeum, and in its botanical gardens murdered Yeres Threem. Cayli refused to belief it until she confronted him and felt his inner Darkness: she fled him, and rather than pursue her, he fled himself, a fugitive of the Galactic Republic.