Jesse Pinkman is a sensitive man. That is why he must be punished.

Yes, the first time we see him on Breaking Bad, he is running away from a crime scene. Yes, over the course of four seasons he has sold drugs, committed numerous thefts and shot people. But that is not why he suffers so profoundly. Jesse’s cardinal sin is sensitivity. He and the people around him have decided that it is an undesirable and unmasculine trait that will doom him to a life of pain and misery.

SPOILERS BEHIND THE CUT

We know very little of Jesse’s life before the series, but what we do know is quite telling. In an early episode we learn that Jesse grew up in an upper middle class home. We see that he was a poor student, but a gifted artist. His room at his parents’ house is filled with high quality comic and cartoon art. We also see that his parents are high-pressure helicopter parents of the first order. His younger brother, Jake, is being systematically groomed and manipulated into becoming a model citizen, filling the mold his parents have crafted for him. His younger brother’s skills fall into traditionally “masculine” spheres. He is academic and athletic, he gets high grades and numerous soccer trophies. Jesse’s skills are traditionally “feminine.” He is artistic and nurturing as we learn from his easy demeanor with kids and from his care for his dying Aunt.

Though it is not spoken or seen on the show, one gets the impression that Jesse’s failure to live up to his parents’ specific expectations and his brother’s facility at meeting the right developmental milestones led him to drug use. The same pressures seem to be cooking Jake as well: he has started smoking joints. When the family maid discovers one hidden in a house plant, Jesse’s parents immediately blame him and kick him out without listening to his explanations. Jesse takes the fall willingly, sparing Jake the inevitable parental fury. In an interesting exchange, Jake tells Jesse that he thinks he is the favorite. It is obvious to the viewer that this is not the case. The Pinkmans can barely look at Jesse and never try to listen to him. But the younger brother feels no love or favortism from his parents, only pressure to fulfill their vision.

In the early episodes of the series, Jesse lives in his deceased Aunt’s house. She left the house to Jesse’s parents in her will, but, if Jesse is to be believed, she intended for Jesse to live there and, when Jesse decided to sell the house, to split the profit with his parents. His parents evict him. Jesse argues that he earned the right to live there because he took care of his aunt while she was dying, but his mom would have none of it. His devotion as the caretaker for a dying woman is meaningless to her. “How did you get like this?" she asks without even listening. No self-reflection, no forgiveness. She and his father are determined that Jesse is no longer their problem. They then renovate the house in an attempt to raise its value, then plan to sell it, keeping all the profit for themselves. They don’t care that he finds himself sleeping in an impounded RV covered in sewage that night. The oversensitive problem child is gone and the house is theirs to sell.

Is it really that surprising that Jesse turned to drugs with such an upbringing? His strengths and successes mean nothing to his family. In place of approval and acceptance, he receives only suspicion and derision.

When Walter White enters his life, Jesse finds a substitute father figure who is capable of offering approval, however infrequent. Walter puts Jesse in a position where he could earn a great deal of money, but only at the expense of suffering constant physical, verbal and emotional abuse and psychological manipulation since Walter sees Jesse as a means to an end. Walter cares for Jesse in his way, but Walter’s biggest concern is his own pride and profit, and he is only helpful to Jesse insofar as it doesn’t hinder his plans, barring a major exception at the end of season 3.

While Walter does bring Jesse economic opportunity, he does not offer Jesse a chance to excel at his greatest strengths. He needs Jesse because Jesse understands the drug culture and is an able lab assistant. He does not need Jesse because he is good with kids or because he can draw well.

The only times we really see Jesse happy are with his two girlfriends. His first girlfriend, Jane, engages with his inner artist, flirting with him over his superheroes and taking him to a Georgia O'Keefe exhibit. The two plan to run away together with Jesse’s drug money. Jesse confides in her that Walter owes him a lot of money. Jane, being far more assertive than Jesse, blackmails Walter into giving Jesse his cut. Walter retaliates by letting her choke on her own vomit.

Jesse’s second girlfriend, Andrea allows him to engage in his more nurturing side by letting him form a relationship with her son, Brock. Walter arranges an end to that relationship as well, since he poisoned Brock as part of an elaborate attempt to kill a rival and he was afraid Brock would figure out what happened and tell Jesse.

Without his girlfriends, Jesse’s default state can best be described as one of pure misery and anhedonia. He goes to rehab and comes to the realization that "I’m the bad guy." He goes to a support group and goads the other addicts into telling him he is irredeemable and kicking him out. He tries to drown out the world by holding massive drug-fueled parties, hoping the joy of others might rub off on him. It doesn’t work. He has no effective outlet for his better self. The usual trappings of monetary success, the way American men are taught to keep score, hold no joy for him. At one point he even allows someone to walk off with thousands of dollars of his money. He doesn’t care. In the latest episode he is more than happy to give away large chunks of his share of a big take. Money’s not how he measures success. He measures success through belonging and being valued.

Beyond his unmasculine skill set, Jesse is highly emotional. He probably cries more than any other male character on TV. He has plenty of understandable reasons to do so. He is beaten regularly, his best friend was murdered, his girlfriend choked to death on her own vomit and he is made homeless by his parents TWICE. He seems to be a magnet for the worst life has to offer. However, in most cases he is not crying because he is sad, but because he blames himself, failing to see his own worth, even though he is usually not truly to blame.

The central tragedy of Jesse’s character is that it is easy to see the decent compassionate person he could have been, even as he is pushed to do more and more dispicable things. Had he been allowed to pursue his true self, and not learned that who he was was insufficient, he could have found a great niche for himself, perhaps as an elementary school teacher or a nurse. His parents and Walter had no use for the "weak” and “feminine” parts of Jesse. They taught him that he was worthless and that it is wrong to be empathic rather than aggressive. Until he finds a way to accept the parts of himself he has been taught to reject, Jesse will be one of the most painfully tragic and utterly compelling characters on television.