Summary

• Characters in Boardwalk Empire often meet tragic ends, even the lead characters, as shown by Nucky Thompson's demise by a once-patroned young boy.
• Mickey Doyle, a comic relief character, met a grim end after failing to reason with Luciano, who saw him as dispensable in the crime world.
• Pearl, an innocent caught in the crossfire, dies tragically due to Liam's attack, taking her own life in the despair of shattered dreams.

HBO has created some of the best shows on television over the last few decades, and Boardwalk Empire is an early example of this. Based on the real-life figure of Enoch L. Johnson, Boardwalk Empire tells the Prohibition-era story of Nucky Thompson (Steve Buscemi), a man who was both a politician and a crime kingpin in Atlantic City. Throughout the series, Nucky meets and deals with several fictional and historical characters in this crime drama, including mobsters, government agents, politicians, and more.

At its heart, Boardwalk Empire is a period crime drama based in the world of organized crime, and Boardwalk Empire covers dozens of plot threads and characters from all over the spectrum. 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. This ends up as a fact, with many characters coming and going throughout the series. By the time the show ended after five award-winning seasons, no one was safe, not even the lead characters in the series.

Mickey Doyle

Shot by Lucky Luciano in 1931

In the underground world of Prohibition-era gangsters, it's to be expected that most of them aren't going to survive in the game. And given how untrustworthy Mickey Doyle seemed to be, it's surprising he managed to survive for as long as he did. Doyle's sense of humor, ambition, and his lack of loyalty to others often cause problems for him. While he is a shrewd manipulator, Mickey is also someone who made plenty of enemies, but somehow found a way out of problems time and time again.

His end came after Nucky sent Mickey to force a meeting with Luciano by kidnapping his associate, Benjamin Siegel. However, Luciano wants everything Nucky has — including the club Nucky just gave to Mickey. Mickey tries to reason with him, so Luciano shoots Mickey in the throat, killing him. In Boardwalk Empire, Mickey was one of the few comic relief characters in 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

Death By Suicide (Gunshot)

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 actual 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.

Pearl's death was sad because it was something she didn't deserve, and she only died because of her connection with Jimmy. Liam, an Irish gangster who works for crime boss Charlie Sheridan, attacks Pearl and mutilates her face to send a message to Jimmy. While Jimmy gets revenge and kills Liam, a despondent Pearl realizes that her dreams of becoming an actress have ended because of this. Pearl dies by suicide during an opium-induced haze instead of continuing to live this way.

Billie Kent

Dies In The Explosion Of Babette's.

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 wars. Billie Kent is a prime example of this sad truth. 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 have gone to Babette's Supper Club, the club suddenly explodes. Nucky survives, but Billie doesn't. Ironically, the explosion was specifically meant to kill Nucky (via a bomb made by Gyp Rossetti). However, it was Billie who died instead, and her only crime was falling in love with Nucky. It was also very sad because Billie had just won a role in her first movie before her death, and once again, someone died before reaching their ultimate dreams thanks to Nucky and his cohorts.

Eddie Kessler

Death By Suicide (Jumps From Window)

There are very few people in the world whom 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 the authorities, and he ultimately confesses to his crimes after they put the squeeze on him.

Once he's released, the agents force him into becoming an informant with the threat of deportation. This would cause the shame of returning to face his abandoned family. While this would be terrible for Kessler, he was more gutted by turning on Nucky. Knowing that he can't live with this new life that the agents have forced him into, he dies by suicide. Eddie jumps from a window at the Albatross Hotel, a sad death for a beloved character.

Owen Sleater

Killed By Masseria's Men At A Turkish Bath House

Owen Sleater is an Irish immigrant and works for Nucky Thompson as a driver and bodyguard. However, he was also involved in an affair with Nucky's wife Margaret Rowan, right under his boss's nose. By the time that Nucky and Margaret 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 Owen. Owen and Margaret fall in love pretty quickly, and they carry on an affair, which would prove to be fatal to Owen.

Joe Masseria's men killed him at a Turkish bathhouse in Manhattan (off-screen) when he attempted an assassination of Masseria. To show they know why Owen was there to kill him, Masseria sends Nucky a package late one night, and when he opens it, he sees that Owen's dead body is inside. Margaret is devastated and shortly after, and in the saddest part of his Boardwalk Empire death, it's also revealed that she was pregnant with Owen's child.

Angela Darmody

Shot By Manny Horvitz In July 1921

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, Manny finds Angela instead, in bed with her lover.

Angela begs for her life

Jimmy was on the road to Princeton when this happened, so Manny took it out on Jimmy's wife. Angela begs for her life, but Manny still kills her for revenge, telling her that her death was Jimmy's fault before shooting her in the head. Angela's death drove Jimmy into a drug and alcohol binge as he was depressed and distraught over her senseless death. This sad Boardwalk Empire death led to Jimmy's downfall, as well.

Chalky White

Executed By Firing Squad In 1931

When it comes to Boardwalk Empire characters that actually deserve to die, Chalky White arguably deserves 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. Narcisse leads Chalky outside his brothel and finds several armed men standing there, waiting for him. He then orders the armed men to gun down Chalky. It was a sad death, as he closed his eyes and thought of his daughter singing in his final moments alive.

Nucky Thompson

Shot By Tommy Darmody In 1931

It only made sense that the end of Boardwalk Empire would also mean the end of Nucky Thompson. While it was pretty devastating to see the main character of the series die, Boardwalk Empire itself showed its audience all the reasons that Nucky truly did deserve to die. Much like Tony Soprano in another HBO series, Nucky did plenty to deserve his fate. However, while The Sopranos chose not to go through with showing Tony die (or even get arrested), Boardwalk Empire made Nucky pay for his crimes.

Tommy accuses Nucky of betraying Gillian and shoots him three times

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. 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. What is really sad is that Nucky thought he was helping Tommy by bailing him out of jail and giving him money. Tommy accuses Nucky of betraying Gillian and shoots him three times.

Jimmy Darmody

Shot By Nucky Thompson In August 1921

Boardwalk Empire is a series full of characters 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 decides to work against Nucky and branch out for himself, Nucky feels that he has no choice but to eliminate Jimmy for good.

Jimmy had almost given up on life by this time, anyway. Manny showed up at his house while he was on a trip and murdered Jimmy's wife Angela in cold blood. Her death was as much Nucky's fault as Jimmy's, and this caused Jimmy to turn against Gillian and kill the CCommodore. Knowing that Nucky would never forgive him, he comforted Nucky by explaining that he had truly died during the war, in a trench years ago anyway. Jimmy let him know it was okay and Nucky shot Jimmy twice in the head.

Richard Harrow

Shot In The Chest By Narcisse's Men

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 killer, 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 agrees to one more job for Nucky, though, and when he accidentally shoots an innocent person and gets shot in the gut himself, Richard Harrow decides to just let himself bleed out beneath the boardwalk, dreaming of the life he almost had. Seeing him die, by his own choice, rather than getting help, was a sad Boardwalk Empire moment and shows that no one here really gets a happy ending at all.