Reliving The Most Heartbreaking Moments On ‘Boardwalk Empire’

At once a period piece, mob story, and character drama, Boardwalk Empire (which you can stream on HBO NOW) focused on prohibition-era Atlantic City Treasurer Nucky Thompson, and from there widened its view to glimpse an intricate and vast criminal network over its five years on the air. While the show wrapped the extreme violence into its narrative, it often came out through severe brutality; a kind of non-sensationalized byproduct of the world these characters occupied.

Occasionally, the harshness of this world would catch up to the characters, drawing genuine, heartfelt emotion out of them. We take a look at a few of the times Boardwalk Empire was absolutely heartbreaking. Warning, there are a few spoilers ahead.

Kessler’s Guilt Drives Him To Suicide

For much of the show’s first half, Eddie Kessler was Nucky’s loyal assistant, perpetually at his boss’ beck and call. He even provided him with some limited comic relief due to his less-than-perfect English. While given menial tasks early on, Thompson begins to expand Kessler’s responsibilities when asked to do so.

After celebrating his new promotion, Kessler is arrested by Agent Knox at the train station. Being held up for a day by Knox in a run-down and abandoned room, they uncover a shameful secret from his time as a department store manager back in Germany. He tries to maintain his loyalty, but in the end panics under the threat of deportation and gives the agents a name — Ralph Capone. When asked why he delivered money to the known criminal, Kessler breaks down crying, explaining that he did it because “Nucky told me to.” After being let go, he goes home, dresses himself in his finest suit, and, overwhelmed with guilt, throws himself out of his bedroom window.

Owen Sleater’s Special Delivery

A prominent character in the second and third seasons, Irish immigrant Owen Slater replaced Jimmy as both a bodyguard and enforcer to Nucky Thompson, and was someone who Nucky took great lengths to impart the idea that he was a man to be feared and respected. He was also madly in love with Nucky’s wife, Margaret, and, after a torrid love affair, the two had made plans to run away together and start over with a new life in St. Louis.

As the conflict with Gyp Rosetti escalated over the course of the third season, Nucky intended to assassinate his closest ally, Joe Masseria, sending Owen to a Turkish bath house to do so. That night, Nucky’s awoken to a wooden crate, delivered to his suite at 4 a.m. After opening it, and seeing Owen’s bloody, beaten body inside, Margaret breaks down in tears. In that moment, the look on Nucky’s face shows his realization of their affair while Margaret mourns for not only her lost love, but the lost chance at a new life, once again stuck in the cross-fire of another gang war, this time carrying Owen’s child.

Angela Darmody’s Unexpected Demise

As the season two power struggle between Nucky and Jimmy comes to a head, Jimmy sends Mickey Doyle to pay his debt to Manny Horvitz with $5,000 of reconstituted liquor. Believing that Jimmy was responsible for an earlier attempt on Manny’s life, he forces Mickey to reveal Jimmy’s location, clearly planning to exact revenge.

That night, as Jimmy’s wife Angela lays in bed while her lover, Louise, takes a shower, Manny enters the house, forces Angela from her bed, and shoots Louise in front of her, expecting it to be her husband Jimmy, who is on the road. As Angela collapses, alternately mourning Louise and begging for her own life, Manny tells her, simply, “Your husband did this to you,” before killing her in cold blood.

While Jimmy speaks frankly of losing her to Nucky, pouring a splash of liquor on the floor and proclaiming that it was “to the lost,” it was Jimmy’s friend Richard Harrow seeing the blood and then touching it with his hands that nearly drove him to tears.

Later, Richard would avenge her death by killing Manny outside his home, and when Mickey Doyle began taking credit, Richard showed up to Nucky’s office with a gun to Mickey’s head. When Nucky asked him why he’d killed Manny, who by then was a part of his own crew, Richard answered, simply, “Angela Darmody.”

Richard Harrow’s Death Rattle

Arguably Boardwalk Empire‘s most tragic figure, Richard was a sniper in the first World War, badly disfigured on the battlefield, and forced to wear a tin mask to hide his appearance. Brought into the world of bootlegging by Jimmy Darmody, Richard time and again proves himself as a ruthless and effective killer, but one with a strong moral code.

During the fourth season, Richard and his new wife, Julia, see an opportunity to take custody of Jimmy’s son, Tommy, once his grandmother is arrested for murder. In order to discount her story, Richard asks Nucky where Jimmy’s body is buried. Nucky provides the information on the condition that he complete one last task, the assassination of Dr. Narcisse, the mustache-twirling big bad. He agrees, and after he has him in his sights, he hesitates at the last second, not only failing to kill Dr. Narcisse, but also killing Chalky White’s daughter, Maybelle, instead, while putting himself in a position to take a bullet when trying to escape.

As he manages to get away, we see him meeting his family in Wisconsin (as had been his plan all season) to reconnect with his wife and their adopted son, and to finally live in peace. The longer the sequence plays out, the harder the realization becomes, and, in the end, as Richard returns home with his face fully healed, the shot then cuts to him bleeding out beneath the boardwalk, knowing true peace only in death.

Nucky Gives Gillian To The Commodore

It was a moment that the show had danced around to from the very beginning. While Gillian is locked inside a sanitarium, she sends a letter to Nucky, pleading with him to show the same compassion she had shown him years earlier when they had first met. It’s then revealed through the steady use of flashbacks that when Nucky was still a deputy, he found a young thief who had been stealing from the boardwalk named Gillian. He takes her in, and his wife, Mabel, cares for her, pleading with Nucky to take her in as one of their own.

He’s then offered the role of Sheriff by The Commodore, providing he completes the task of handing off Gillian to him. Nucky, knowing full well what awaits her, lies to her, reassuring her that The Commodore intends to help her, and, most importantly, that he will always be there to look out for her. It becomes the moment where Nucky sells his soul in exchange for his rise to power, and ultimately a course for death and destruction in motion that takes years to play out to completion.