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Recent Immortal Michael Christian has been on an incredible string of luck, taking a number of heads from unarmed and vulnerable opponents, including May-Ling Shen, who taught MacLeod the martial arts in 1780's Mongolia. Christian's Watcher, Rita Luce, has been doing more than just watching, supplying Christian with classified information on the other Immortals and their weaknesses. MacLeod, unaware of Christian, goes on a vision quest to his cabin on Holy Ground — deliberately leaving his sword behind. The race is on for Joe Dawson to figure out Rita's secret before Christian sets his sights on MacLeod.

To save his own hide, petty hoodlum Benny Carbassa, the Nathan Detroit of Immortality, turns MacLeod over to an aging gangster determined to see MacLeod dead before he dies. In the midst of this, Anne returns, having convinced herself that MacLeod will open up in his own time and determined not to push him too hard. In flashback, we see MacLeod's first meeting with Benny, in 1938 at the Coconut Lounge, a club operated by two young brothers who are rivals for the same torch singer.

Lawyer Robert Waverly is leaving his mistress' apartment with his video camera when he sees MacLeod locked in combat with an evil Immortal. Waverly makes sure he gets it all on tape — the fight, the death, the Quickening. He then tries to cut a deal with MacLeod: if MacLeod kills Waverly's wife, then Waverly won't go to the police. When Kurlow, partner of the Immortal MacLeod killed on the tape, comes after MacLeod, Waverly, unaware of what he's dealing with, proposes another deal. A la ""Strangers on a Train,"" Waverly will kill Kurlow and MacLeod will kill Bruno's wife, and no one will suspect a thing. Waverly challenges Kurlow, who kills Waverly easily and MacLeod is left to save Waverly's wife and get rid of Kurlow.

MacLeod is tormented by visions of his own death, beheaded by a mysterious dark-hooded figure. Anne tries to convince him to seek medical help, but instead he turns to his old friend Garrick, who has spent centuries studying the mind. MacLeod saw Garrick in the 17th Century, when MacLeod barely escaped being burned as a witch. What MacLeod didn't know was that Garrick was not able to escape as well. Garrick convinces MacLeod that the dark-hooded figure is a racial memory that haunts all Immortals and that the way to defeat it is to not fight it, to accept it for what it is. When MacLeod, haggard and exhausted, faces the specter for the last time, puts down his sword and refuses to fight it, the figure goes for MacLeod's head — until at the last moment MacLeod realizes the figure is Garrick, seeking his revenge after all these years. In the Tag, Anne, frustrated that MacLeod won't open up to her despite their intimate relationship, leaves him.