Jamie is probably the character we know the least – but he would want it that way. He's cynical, bitter, arrogant, and often mean. He also has some positive sides, though; Jamie is perceptive, speaks his mind, and is often more sensitive than he acts. (If you want to get to know Jamie better, read O'Neill's Moon for the Misbegotten. Jamie is the star of that one.)
So, Jamie isn't all together unlikable. But, basically everything he does is ambiguous: he could be either a cynical, arrogant man who is mistreated by his parents or an embittered man hell-bent on destroying the happiness of those around him.
How far back do we have to go to understand the ambiguity of Jamie's character? The answer is: way back. He's the eldest of the Tyrone children, and was around when baby Eugene died. Or was it murder? Mary seems certain that Jamie intentionally infected young Eugene with measles. But can we trust Mary? She's not the most reliable source of familial detail. Still, we can ask: was Eugene's death the result of a childish accident or murderous jealousy?
In Jamie's favor, he was just seven years old. What's more, despite the string of confessions this evening brings out in the Tyrones, Jamie never comes close to admitting he wanted to hurt baby Eugene.
But speaking of those admissions, Jamie does admit to wanting to ruin Edmund's life. Even though Jamie is completely drunk by Act IV, he's upfront about his jealous and vengeful nature – Jamie even says, "Got to take revenge. On everyone else" (4.1.206).
But why all of this jealousy? His background is a bit confusing. His mother points out that he had "glowing reports" "for years after he went to boarding school," "a fine brain" and "everyone liked him" (3.1.57). All of a sudden, though, he began to drink and was expelled. We never find out exactly why he became an alcoholic.
Well, since Jamie is about ten years older than Edmund, his fall from grace coincides with Edmund's childhood and his mother's turn to morphine. We don't think it's a stretch to assume her drug addiction wasn't great for Jamie's psyche.
There's something else, though, something Jamie makes clear by the end of his confession to Edmund. Jamie yells that Edmund was "Mama's baby, Papa's pet!" (4.1.204) This is when we really see how much Jamie has taken to heart his parents' obvious preference for Edmund.
Throughout the first three acts of Long Day's Journey, Jamie's parents pretty much only address Jamie to criticize him: they find him a lazy waste of money. Mary makes matters worse by overtly favoring Edmund: in response to Doctor Hardy's suggestion that Edmund go to a sanatorium, she responds angrily, "What right has he? You are my baby! Let him attend to Jamie!" (3.1.97).
This situation is particularly difficult for Jamie. He's a thirty-three-year-old live-at-home son. He's by no means an old guy, but his family seems to have completely given up on him. As a result of this environment, it seems that Jamie has given up on himself, too. For comfort, he turns to alcohol, women, and mean-spirited interference in his brother's life.
We've talked about addiction in James's "Character Analysis," so let's leave aside the alcoholism and focus for a moment on Jamie's relation to women. Check out the "Fat Violet" episode: Jamie claims that he sacrifices his own desires by having sex with prostitute Violet in order to save her job (and sense of self-worth).
But is Jamie really doing this for Violet? He seems a bit too satisfied with his "good deed." Moreover, Violet provides an easy source of unconditional affection, something Jamie has never received from his family.
Even if he is acting selfishly, it's hard not to like Jamie and his honesty, despite his dark side. We find his wry quotation of Rossetti particularly apt: "Look in my face. My name is Might-Have-Been; / I am also called No More, Too Late, Farewell."
See, Jamie quotes this line mockingly, with more than a hint of self-criticism, but it's actually the grim truth. Jamie is, in our opinion, a strong candidate for saddest character in the play, because he's the only person nobody seems to love anymore. He's been lost, and there's no one to find him. Jamie's an essential foil for Edmund, because he's Might-Have-Been, the opposite of the Golden Boy: he's wrecked everything in his life, and he knows it – and he can be honest with himself and with his family about his many failings.
Jamie, like the rest of his family, gives us a memory filled monologue in Act IV. He tells Edmund that he's always resented him, and he turned his younger brother on to drinking in hopes of destroying him. This hurtful admission is another example of how O'Neill's characters move backwards in time in the play. Check of "What's Up with the Ending?" for more detail.James Tyrone, Jr. (Jamie) Timeline