The more talented of the two lawyers, Lilah and Lindsey are great competitors who fight eachother for the top positions at Wolfram and Hart. Early on in the fight against Angel, Lindsey is fighting his conscience as he knows about a group of children who are to be killed. Despite this show of morality, he makes a decision to stay with Wolfram and Hart, which results in the loss of his hand in a fight against Angel. This he plans to take vengeance for, but is soon distracted by his love for Darla. When Darla becomes a vampire again, and attacks the lawyer, he is the only one who isn't afraid.

His life, along with Lilah's is spared by Darla, as she wants to keep a connection open with Wolfram and Hart. Lindsey continues to protect her despite the apparent lack of love Darla shows for Lindsey. Her ultimate betrayal occurs though when she sleeps with Angel. Lindsey blames Angel though, and goes after him with a sledge hammer.

After losing this fight though, he is rewarded at Wolfram and Hart with a new hand. He is then also given the chance to be promoted as the sole head of special projects, at the expence of Lilah. However, the hand he is given is evil, something he only sorts out with Angel's help (see Dead End).