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Breaking Bad’s Most Heartbreaking Jesse Pinkman Moments

Jesse Pinkman is not an innocent guy yet Breaking Bad makes it impossible for us not to root for him. We want him to get out, to get clean and sober, and to break away from Walt and the mess he’s created, but death follows him wherever he goes. There are moments in the series where Jesse almost breaks free from it all only to be dragged in deeper and deeper. Some of these choices are his own and some are forced upon him by others, but regardless, Jesse suffers deeply for his sins and the sins of those around him. So, in honor of El Camino finally coming to our screens to continue Jesse Pinkman’s story, the following are my picks for the most tragic Jesse moments in Breaking Bad.

The Death of Jane Margolis

Jesse Pinkman hovers above the body of Jane Margolis and cries

When Jesse meets his neighbor and landlord Jane Margolis, she doesn’t trust him. As a former addict in recovery, she knows exactly what he is and what he’s about. Despite all of this, though, she ends up falling for him. At this point, Jesse is still grieving the loss of his friend (and dealer) Combo, and one hopes that maybe Jane being in recovery herself could be the positive influence he needs in his life. Maybe she could help him get clean and they could have a long, healthy relationship—the only relationship in Jesse’s life that isn’t completely toxic.

But this is Breaking Bad, so of course, the opposite happens. Instead of Jane being a positive influence on Jesse, Jesse’s drug use causes Jane to relapse. She made her own choice, of course, but one can’t help but wonder if she would have been able to stay clean if Jesse had never moved in next door. But that isn’t what happens. Jesse and Jane get deep into the drugs and Jane introduces Jesse to heroin (which was her drug of choice).

Walt had always been critical of Jesse’s drug use. Much as I am loath to admit that Walt is right about anything, this is one thing I actually agree with him on (although Walt’s reasons for wanting Jesse clean are purely self-serving). As it turns out, Walt is right not to trust Jesse in his drug-addled state because not only does he cause them to almost miss a major deal, his relationship with Jane (and her ill-advised suggestion to blackmail Walt) is the final nail in her coffin. As Jesse and Jane are passed out in a heroin stupor at his apartment, Walt attempts to wake Jesse and, in doing so, flips Jane onto her back. She begins to overdose and choke on her own vomit and because Walt is an absolute monster he just lets it happen. Bryan Cranston has said that that scene was one of the most haunting he ever had to shoot for the series, and with good reason. It’s horrifying to watch, and the fallout will be swift and severe.

Jesse is absolutely devastated by Jane’s death. Initially, when Mike Ehrmantraut arrives to do clean up, Jesse is completely in shock. In the aftermath of Jane’s death, Jesse ends up in a drug den, nearly overdosing himself. As Walt comes to get him, he starts bawling and tells him, “I killed her…I loved her more than anything.” Aaron Paul’s acting is always top-notch, but this moment of raw emotion—the depth of his guilt and grief—is, for me, one of the most heart-wrenching moments of the series.

Jesse Pinkman Murders Gale Boetticher

Jesse tears up as he points a gun towards Gale Boetticher

This one is a real doozy because it is the moment when Jesse really does sell his soul. Jesse is a lot of things but he was never a straight-up murderer—until he was. When Walt figures out that Gus has been grooming Gale to take over for him so that he can cut Walt and Jesse out (and likely take them out as well), Walt tells Jesse that Gale has to die. Jesse so desperately doesn’t want any part of that that he suggests that Walt go to the DEA and take a witness protection deal and that he will just go on the run. At this point, Jesse has accepted that things are over for them and he’s ready to cut and run—but not Walt.

Walt is incapable of admitting defeat and he convinces Jesse that the only way he can keep him alive is if Gale dies. Jesse keeps pleading with Walt that there has to be another way but Walt reminds Jesse: “I saved your life, Jesse. Are you gonna save mine?” And so Jesse agrees to get Gale’s address so that Walt can do the dirty work. His hands would never have been clean on this one no matter how things shook out. But, per usual, things don’t go according to plan. Walt gets snatched up by Victor and taken to the lab where Mike is waiting to take him out. Walt manages to bullshit his way out of the situation by telling him he will give up Jesse, which gives him the opportunity to call Jesse and tell him he’s got to go do the hit immediately or they are both dead men.

And so he does it. Jesse Pinkman goes to Gale’s apartment and shoots him point-blank in the face. He didn’t have to do it. He could have gone to the police instead of going to Gale’s apartment. He could have taken off on the run and left Walt to the punishment that, frankly, he deserved. But despite how incredibly toxic their pseudo-father/son relationship is, at this point, Jesse still feels like he can’t let Walt die. The look of absolute anguish and horror on his face when he kills Gale tells us all we need to know about exactly how much of his soul he lost at that moment.

Todd Alquist Murders Drew Sharp

Drew Sharp sits on his dirt bike in the desert, waving to Walt, Jesse, and Todd

The murder of 14-year-old Drew Sharp is arguably the worst thing to happen in all of Breaking Bad. A lot of people die throughout the series—some of whom had it coming and others who didn’t—but when you’re talking about a completely innocent child who absolutely 100% did not have to die, it’s a whole different story. This one is actually not at all on Jesse; Todd Alquist is completely to blame for this heinous and unnecessary act. But it affects Jesse deeply because, as we have seen throughout the series, he has a very soft spot for children.

Drew Sharp died because he was in the wrong place at the wrong time, specifically the methylamine train heist. The heist itself went off perfectly. They got what they needed without anyone being the wiser. But then, after the fact, Drew Sharp came along on his bike. He didn’t see anything. He had absolutely no idea what had gone down or even that anything had gone down at all. To Drew, they were just three men out in the desert, and Drew waves hello at them.

They could have just waved back and let him go on his way, and Walt and Jesse probably would have done just that if it were just the two of them. However Todd, believing that there could be no loose ends, shoots Drew Sharp dead without a second thought. He shows absolutely no emotion or remorse. To Todd, who is arguably the most psychopathic person in all of Breaking Bad, killing an innocent young boy was just the cost of doing business. Regarding the incident, he later tells Jesse, “Shit happens.” He has absolutely no remorse and is seemingly incapable of normal human empathy, where one of Jesse’s defining character traits—and the one that fuels the vast majority of his conflict and character development—is being far too empathetic for his line of work.

Jesse is obviously gutted by this. At this point, he’s already been completely destroyed emotionally by various events in his life, but Drew Sharp’s death hits him hard. For all the times he’s wanted to get out, and all the times he has tried and failed, being a part of something where it’s business as usual to murder a kid and dissolve his body in acid is absolutely beyond the pale. When Walt and Mike vote not to fire Todd and Walt appears seemingly unaffected by the Drew Sharp incident, Jesse finally decides he is out for good.

The Nazis Make Jesse Their Meth Slave

A bloodied Jesse Pinkman is chained up in the Nazis' meth lab

Jesse Pinkman has had some very low lows but I think being enslaved in an underground cage, only to see the light of day when he is forced up into the Nazis’ meth lab, chained, and forced to cook for them is about as low as things get. He tried to get out of the business for good after Drew Sharp’s murder, and he almost made it, too. He even cooperated with his mortal enemy Hank Schrader to try to bring Walt down. But we all know what happened to Hank and his partner Steve Gomez in their attempt to bring Walt in, and in the aftermath of their deaths Walt proved himself to be the exact level of monster I always knew he was. He gave Jesse up to the Nazis to save his own ass and, as a final fuck you, he told Jesse he killed Jane.

Jesse is so shattered that the Nazis have to literally drag him off into meth slavery. At that point, Jesse is an absolute husk of a human being. He has absolutely no one and nothing in his life. And the worst part of it all: he has to deal with Todd Alquist, child murderer. Todd, being the psychopath that he is, tends to Jesse’s needs—giving him a little treat in the form of a bowl of ice cream and keeping the tarp off the top of his cage so he can see the stars at night—and actually thinks that he’s being kind to Jesse. But he never lets Jesse forget that they know exactly where his ex-girlfriend Andrea Cantillo lives with her son, Brock, and even puts up a picture of them that he can look at while he’s chained up cooking meth for them day-in and day-out. It’s safe to say that this is Jesse at him most miserable—well, almost…

Andrea Cantillo Is Murdered to Punish Jesse

A gagged Jesse screams and cries as he watches Todd murder Andrea

And now we’ve finally reached it: Jesse’s lowest low of all possible lows. What’s worse than one dead girlfriend on your conscience? TWO dead girlfriends on your conscience (with a bonus orphaned child). As it turns out, even as a meth slave, Jesse still had a bit of fight left in him. He used Todd’s “kindness” to get him to leave the cage exposed and planned an escape, and it actually worked. He was free, and he ran, but he didn’t get far. They caught him before he made it off the compound, and his transgression would not go unpunished.

Of course, they can’t kill him. They need him to cook since Todd’s abilities are sub-par and the love of Todd’s life, Lydia Rodarte-Quayle, will not accept anything less than the Heisenberg-level stuff. So what do you do to punish a man who has absolutely nothing left to lose? You find the one thing in the world he still cares about. Jesse and Andrea have not been together for some time, but he still very much cares for her and for Brock. The Nazis know this, so they decide to kill Andrea to punish Jesse and make sure he never, ever tries to escape again. What’s worse is they take him with them to the hit and make him watch as Todd murders her. His anguished screams in the car are the death throes of his will to live, and after that Jesse truly has nothing left. Well, nothing except Brock, who will be the next to die if he steps one toe out of line.

And that’s where we find Jesse Pinkman at the end of Breaking Bad. Totally broken and still in servitude to Todd and the rest of the Nazi scumbags. But Walt does one last kindness to Jesse when he arrives to take everyone out. Jesse gets the satisfaction of killing Todd (and the satisfaction of not killing Walt even though he expects/wants him to). Instead, Jesse gets his freedom and the final shot we get is him driving off to parts unknown, maniacally scream-laughing into the night.

And that was that—or so we thought. The announcement of El Camino and a Jesse-centric Breaking Bad movie really changed the game and left fans speculating as to what the film would have in store for Jesse Pinkman. El Camino is now available to stream on Netflix so go check it out and find out what new forms of suffering Vince Gilligan has decided to inflict on poor Jesse.


Written by Ali Sciarabba

In addition to her position as TV Editor and Writer for 25YL, Ali Sciarabba is a freelance editorial consultant and author of numerous nonfiction reference books for middle school and high school students. In her spare time she enjoys obsessing over various television shows, especially Breaking Bad and Better Call Saul. When not overanalyzing TV shows, she is wrangling her Corgi, Cassidy, who is inarguably the cutest dog that has ever existed.

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