HBO has certainly developed a reputation as the source for the best shows on television, and that reputation is well earned. Honestly, before HBO decided to really up their game when it came to original content, prestige television that had the production value of an expensive film and was meant to be art as well as TV really didn’t exist at all. And one of their most spectacular forays into prestige television is undoubtedly their Prohibition era crime drama, Boardwalk Empire.
Boardwalk Empire is ostensibly about of Nucky Thompson, the crime kingpin of Atlantic City, but the story itself had a scope that covered dozens of plot threads and characters all over the country. And as a show about the criminal underground in America, it was safe to expect that many of the characters in the series would die in their pursuits. And die they did. Plenty of characters came and went on Boardwalk Empire, but here are the 10 saddest deaths in the entire series, ranked.
Mickey Doyle
In the underground world of Prohibition era gangsters, it’s to be expected that a fair bit of them aren’t going to survive in the game. And given what a hapless idiot Mickey Doyle seemed to be, it’s honestly pretty surprising that he managed to survive for as long as he did. But he doesn’t belong on this list because his death was particularly tragic or shocking; he’s here simply because he was one of the few comic relief characters on the series, and losing him was a sad and palpable loss. He offered something to Boardwalk Empire that no other character did and it was tough to lose that.
Pearl
Like many of the minor characters on Boardwalk Empire, Pearl really had nothing to do with the crime business but was just unlucky enough to get caught in the crossfire of the never-ending war between the real criminals.
Pearl was a prostitute who caught Jimmy Darmody’s eye, and the fact that Jimmy liked her so much is exactly why she ultimately wound up dead. Initially, Pearl’s face was just violently mutilated as a message to Jimmy, but once a despondent Pearl realizes that her career is over, she decides to kill herself instead of continuing to live this way.
Billie Kent
The women on Boardwalk Empire who are unlucky enough to become the object of affection to one of the major players in the crime world often become the collateral damage in the inevitable. And Billie Kent is a prime example. Billie Kent became Nucky’s mistress in Season 3, and although she prided herself on her independence, she had no problem letting Nucky sweep her off her feet. One night after the pair has gone to Babette’s Supper Club, the club suddenly explodes. Nucky survives, but Billie doesn’t, and ironically the explosion was specifically meant to kill Nucky.
Eddie Kessler
There are very few people in the world who Nucky Thompson could rely on, but his longtime valet Eddie Kessler seemed to be one of them. After being in Nucky’s employ for years, Eddie decides that he wants to take a bigger role in Nucky’s organization and he starts partaking in actual criminal activities instead of just taking care of Nucky. But that decision seems to be a mistake, as Eddie’s quickly taken in by authorities and he ultimately confesses to his crimes after they put the squeeze on him. And once he’s released he is so gutted by mistakenly turning on Nucky that he commits suicide.
Owen Sleater
By the time that Nucky Thompson and Margaret Rowan actually wind up getting married, their relationship seems to be almost entirely loveless. Neither one of them seems to be particularly bothered by this arrangement though, at least until Margaret meets Nucky’s new right-hand man, Owen Sleater.
Owen and Margaret fall in love pretty quickly, and they carry on an affair right under Nucky’s nose. But late one night, Nucky is delivered a package. When he opens it, he sees that Owen’s dead body is inside. Margaret is devastated and shortly after, it’s also revealed that Margaret was pregnant with Owen’s child.
Angela Darmody
When Jimmy decided that he wanted to be the top dog in Atlantic City, it was only a matter of time before the people that he loved got caught in the crossfire, primarily his wife Angela — who absolutely did not deserve the fate that was doled out to her. Crime boss Manny Horvitz apparently didn’t bother doing his research when he decided to come to Atlantic City and eliminate Jimmy, because when he arrives at the Darmody home, he finds Angela instead. Angela begs for her life, but Manny still kills her for revenge, telling her that her death is Jimmy’s fault before shooting her in the head.
Chalky White
When it comes to characters that actually deserve to die, Chalky White arguably deserved it more than most. He at least knew the kind of business he was in, and he had been responsible for countless deaths before his own. However, he was undeniably one of the best and most interesting characters in the entire series, and it was tough seeing him bested by the insufferable villain Valentin Narcisse. Chalky was willing to put his life on the line to save the woman that he loved from Dr. Narcisse, but his attempts to rescue her from his clutches failed, and he wound up on the wrong end of a bullet.
Nucky Thompson
It only made sense that the end of Boardwalk Empire would also mean the end of Nucky Thompson, and while it was pretty devastating to see the main character of the series bite the dust, Boardwalk Empire itself showed its audience all the reasons that Nucky truly did deserve to die.
It was pretty poetic justice that the result of Nucky’s original sin, Tommy Darmody, was the one to come back and kill Nucky in the end, and it was interesting to see that no matter how successful someone is or how much they get away with, everyone has to pay for their misdeeds eventually.
Jimmy Darmody
Boardwalk Empire is a series chock full of characters who are mired by tragedy, but there are few characters who are truly more tragic than Jimmy Darmody. As a child who was the result of Gillian Darmody’s rape when she was only a child herself, Nucky Thompson seemed to feel guilty for his existence and therefore cared for him almost like his own son. But when Jimmy decided to work against Nucky and branch out for himself, Nucky felt that he had no choice but to eliminate Jimmy for good. And eliminate him he did, although Jimmy comforted Nucky by explaining that he had truly died in a trench years ago anyway.
Richard Harrow
Anyone who expects a character in Boardwalk Empire to get a happy ending doesn’t understand the show that they’re watching — but if there was ever a character who truly deserved a happy ending, it’s Richard Harrow. Yes, he’s a serial murderer, but after the physical and mental trauma of WWI, it seemed like Richard was never going to care if he lived or died, and he would be permanently stuck living this half life forever. But after years of growth and healing, it seemed like Richard was going to finally get his happy ending. He agreed to one more job for Nucky, though, and when he accidentally shoots an innocent person and gets shot in the gut himself, he decided to just let himself bleed out beneath the boardwalk, dreaming of the life he almost had.
