Season one

Born into a dirt-poor dysfunctional family in the south-central United States, Lindsey worked hard to overcome his upbringing. (His exact origin is ambiguous; though he has an Oklahoma license plate on his truck in "Dead End", Angel comments in "You're Welcome" that Lindsey was "a tiny Texan." It is possible that Lindsey's origin story is meant to mirror the personal history of Christian Kane, who was born in Dallas, Texas, but grew up primarily in Norman, Oklahoma.) While studying at University of California, Hastings College of the Law, Lindsey was recruited for the corrupt corporation known as Wolfram & Hart. Starting in the mailroom, he quickly worked his way up, becoming one of Wolfram & Hart's most valued lawyers.

His good looks are only surpassed by his ambition. Lindsey legally represented many a vampire and demon, as well as evil humans. He meets Angel in the first episode in the series, when Angel kills Russell Winters, one of his vampire clients, by hurling him out the window of a tall building just after Lindsey had claimed that Angel couldn't touch the client in question. From that point on, Lindsey works to kill Angel, and is the co-architect of a plan to hire renegade Slayer Faith to do just that. This is not particularly well-received by his superiors, who want to keep Angel alive for their own reasons.

Lindsey experiences a crisis of conscience later, when Wolfram & Hart plan to kill a small group of innocent children, and he and Angel strike up a temporary alliance and are able to save the youngsters. After this, he is poised to leave Wolfram & Hart, but is wooed by a promotion and stays, becoming an integral player in the plan to resurrect Darla. During the ensuing battle, Angel chops off Lindsey's hand, forcing Lindsey to use an artificial one. This only further cements his hatred for Angel.

Season two

When Darla is returned to life, Lindsey becomes enamored with the now-human Darla, and is present when she is re-sired by Drusilla. His infatuation does not end when Darla becomes a vampire, and he is one of only two spared by Darla and Drusilla in the massacre in Holland Manners' wine cellar. With only him and Lilah Morgan left of Wolfram & Hart's Special Projects Team, their rivalry reaches an all-time high as the two start a power struggle for the vice-presidency of the team.

Darla manipulates Lindsey's feelings, which she never reciprocates, to gain his help after Angel sets her and Drusilla on fire. Darla stays at Lindsey's house, manipulating him to gain insight into Wolfram & Hart, and attempts to steal a mystical ring from the Senior Partners. Angel is at the meeting and beats her to the ring, and she is almost staked by guards but Lindsey saves her. After finding Darla with the ring, he figures out that Darla has slept with Angel.

Lindsey responds by brutally beating Angel with a sledgehammer, as well as hitting the vampire with his truck a few times, demanding to know what happened with Darla. Angel eventually gains the upper hand, smashes Lindsay's artificial hand, and steals his truck. Returning to his apartment, Lindsey finds that Darla had left town, taking all her clothes with her. Lindsey is left alone, beaten up both physically and emotionally.

Consequently, his work at the firm suffers, but he is still in a race with Lilah for the promotion. Hoping that his performance will pick up again with the return of his hand, Lindsey's superiors arrange for him to receive a mystical transplant, but the new hand acts up, writing "kill" whenever Lindsey doesn't concentrate. Fearing that the hand is evil, Lindsey goes to Caritas and sings for the Host, revealing that he used to be a regular customer and musician at Caritas until he lost his hand.

Lorne sets him and Angel on the path that will end with the two working together to discover a Wolfram & Hart facility that specializes in unwilling limb donors. Among them is the donor of Lindsey's hand, an old friend of his from his mailroom days. After figuring out that his hand isn't evil but rather suicidal, Lindsey pulls the plug on his friend and destroys the facility, while saving those that can still be saved. It is then that Lindsey decides to leave Wolfram & Hart permanently.

In a last confrontation between Angel and Lindsey, the two bury the hatchet, and Lindsey warns him of the games Wolfram & Hart is trying to play. Lindsey leaves Los Angeles and goes on a soul-searching trip, including, amongst other places, Nepal. He does not reappear for two seasons.

Season five

In Season Five of Angel, Lindsey finally returns to Los Angeles, when he learns that Angel has taken over the Los Angeles division of Wolfram & Hart. Although it seemed that he and Angel had buried the hatchet, Lindsey is unable to cope with the fact that Angel has gotten so easily the job that Lindsey had fought so hard for. His hatred for Angel returns in full force. Runic tattoos cover Lindsey's body, mystically hiding his presence from the Senior Partners. At some unrevealed point, he begins a relationship with Eve for whom he shows true affection.

Together, Lindsey and Eve manipulate events so that Spike, not Angel, proves (or at least appears to the Senior Partners) to be the ensouled vampire foretold in the Scrolls of Aberjian, the one who will have a crucial impact in the Apocalypse and fulfill the Shanshu Prophecy. Lindsey hopes that once the Senior Partners realize the folly of attempting to seduce Angel to their cause, that he will be stripped of his position at Wolfram & Hart, leaving a power vacuum which Lindsey could fill, gaining a measure of revenge on Angel.

The seeds of this plot are planted in the finale of Season Four of the series when Angel is given the amulet which Spike eventually uses to destroy the Hellmouth in Sunnydale. Deposited, incorporeal, in Wolfram & Hart and unable to leave the city limits, Spike gradually grows attached to the city and reconsiders his initial intention to seek out Buffy in Europe.

Lindsey then initiates the next stage of his plan, making Spike corporeal again via what is likely a spell sent in a package to Spike at Wolfram & Hart. He later seeks out Spike under the assumed identity of a drifter named Doyle, closely paralleling the initial encounters between Angel and the real Doyle. Claiming to receive visions from the Powers That Be, he gains Spike's cooperation and trust.

Lindsey and Eve contrive a situation where Spike saves Angel from a demonic parasite (placed on an unconscious Angel by Eve), which simultaneously disheartens Angel, galvanizes Spike, and adds weight and veracity to the claims made by 'Doyle'/Lindsey. Although the 'mind numbing' visions that Lindsey reports are non-existent, the events described (whether revealed to Lindsey through mundane or arcane means) are true, and for a time, Spike does appear the far more likely candidate to fulfill the Shanshu Prophecy.

However, when Cordelia seemingly returns to life, it throws a monkey wrench in Lindsey's plans. Lindsey sends Spike to kill her, not expecting him to succeed, but it "was worth a shot." Meanwhile, he infiltrates Wolfram & Hart. When informed by Eve that Spike had failed, Lindsey activates the Senior Partners' program meant to kill Angel if he turned against them. The plan is averted though as Spike, Cordelia, and Angel are able to uncover Lindsey's actions.

Angel and Lindsey face off in the chamber where the "contingency plan" is stored. The pair fight on a rising container, that holds the creature meant to kill Angel while Cordelia tries to stop the process. Lindsey displays the new abilities he has learned on his journeys, enabling him to keep up with Angel in a physical confrontation. Despite this, Angel finally defeats Lindsey, informing him that, no matter what he tries, he (Angel) will always beat the bad guys, and his comrades are able to dissolve the tattoos that protect Lindsey from the Senior Partners' wrath.

Lindsey is incarcerated in a hell dimension which emulates suburbia, complete with a wife and son. Time operates in a loop; each day he has his heart cut out by a demon hiding in the house's basement, reminiscent of the myth of Prometheus. He is eventually rescued by Angel, Spike, and Charles Gunn for information they need. They are only able to leave by the sacrifice of Gunn, who remains behind to take Lindsey's place.

Lindsey later reveals the existence of the Circle of the Black Thorn, the Senior Partners' instrument on this plane, a secret society devoted to maintaining man's inhumanity to man in exchange for power. He notes that while Angel is sidetracked at Wolfram & Hart, the Apocalypse is already underway, and Angel and his team are becoming more and more corrupt by the day.

Lindsey and Angel ally once more in an effort to stop the Circle. The two agree to fight the upcoming battle together and at the end, resolve their differences, maybe even allowing Lindsey to take a powerful position at Wolfram & Hart as "the devil they know." At least that is the plan.

Lindsey destroys the Sahrvin demon clan with Lorne's assistance as planned. However, Angel knows that Lindsey can never be trusted. Consequently, Angel secretly instructs Lorne to assassinate Lindsey once the Sahrvin are eliminated. Lindsey insists to Lorne that he has changed, even joking, "I can sing for you", so Lorne may read his future. Lorne coldly remarks, "I've heard you sing." and fires two bullets into Lindsey's chest. Lorne tells him that he already knows Lindsey will never be on the side of good. A stunned Lindsey slumps against by a wall, outraged and humiliated at having met his end at the hands of a "flunky," rather than his nemesis, Angel.