The epic period gangster series Boardwalk Empire provided five seasons of compelling drama and graphic violence amidst the backdrop of bootlegging in Atlantic City during the Prohibition Era. While the HBO hit mostly focused on the rise and fall of politician turned crimelord Enoch "Nucky" Thompson, the allies who ed his empire and the enemies who tried to dismantle it became as significant to fans as the man himself.
Every character in Nucky's line of work was no stranger to tragic endings, and over the odyssey of his life of crime, many fan favorites met their demise at the end of a gun, through the dissolution of important partnerships, or via the destruction of their reputations. Some of them got the ending their actions all but guaranteed, while others were simply the victims of bad luck or bad writing.
Fitting Ending: The Commodore
Part of the backbone of iniquitous ventures in Atlantic City, the Commodore was responsible for fueling the economic prosperity of the city through various criminal enterprises, most prominently bootlegging. A vindictive, petty, and deplorable businessman, he not only groomed Nucky Thompson to take over as powerbroker of Atlantic City, but he also groomed Gillian Darmody as his lover when she was barely a teenager.
In a righteous maneuver that reflected an enslaved Princess Leia choking the lugubrious Jabba the Hutt in Return of the Jedi, Gillian Darmody got her revenge decades later by not only severely beating the Commodore but smothering him with a pillow.
Deserved Better: Jimmy Darmody
Former protégé of Nucky Thompson, Jimmy Darmody eventually moved on to his own criminal enterprises after being ed over for a promotion and disagreeing with Nucky's leadership and direction. Partnering with his father the Commodore, Jimmy began to have second thoughts after it was clear Thompson might be killed.
Jimmy Darmody's untimely demise at the end of Season 2 felt disted and sudden. Rumors circulated after actor Michael Pitt wasn't present for the "Farewell Boardwalk Empire" special that he had been fired from the series for unprofessional conduct, but writer Terence Winter has always maintained while Pitt could be "intense", Jimmy would have always died at Nucky's hands. Whatever the truth of the matter, the execution of the execution could have happened in a way that honored the character's journey in a more meaningful way.
Fitting Ending: Gyp Rosetti
Gyp Rosetti became the main thorn in Nucky Thompson's side in Season 3 when he decided to outgrow his role as a lieutenant for Joe Masseria and embark on his own criminal schemes. Irascible and easily offended, the New York City gangster was known for exacting extreme vengeance for small perceived slights.
After taking over large swathes of Nucky's enterprise in Atlantic City, Rosetti thought himself the territory's biggest crimelord until he was betrayed by one of his own men, who didn't take kindly to Rosetti killing his cousin. Being literally stabbed in the back was exactly what an arrogant goon like Rosetti deserved.
Deserved Better: Angela Darmody
Married to Jimmy Darmody when she was still a child herself, Angela Darmody suffered as a thankless wife and mother, with a tragic story of neglect over the course of the series. No sooner had she just been able to live authentically and garner some modicum of happiness than she was gunned down by Manny Horvitz.
Though Richard Harrow eventually avenged Angela by murdering the Butcher with a shotgun at close range, Horvitz getting his comeuppance did little to assuage fans who felt that Angela's demise was cold and heartless, only serving to further the stories of more prominent characters.
Fitting Ending: Gillian Darmody
With her depraved backstory and horrific childhood, Gillian Darmody didn't stand much of a chance of growing into a stable, well-rounded human being. After having the Commodore's child at such a young age, she obsessively clung to her son Jimmy for security, twisting their relationship into something corrupt and disturbing.
Gillian used her wiles to manipulate powerful men, the currency of the flesh paving the way for her to gain an ounce of influence in Atlantic City. Unfortunately, after Jimmy's death in Season 2, she began to lose her grip on her sanity and reality, and ended up being left alone in an institution.
Deserved Better: Nelson Van Alden
Out of all the characters on Boardwalk Empire, Nelson Van Alden underwent the most salient change. His progression from puritanical religious zealot to intimidating muscle for mobsters made Van Alden a fascinating character to watch, but his story became increasingly orbital to the main events of the series.
Leading the double life of Agent Van Alden/George Mueller ultimately came to a head when he was nearly unmasked by Al Capone. Just before Van Alden could kill the mob boss, he was shot by federal agent Malone, who couldn't risk being exposed in Capone's crew. The attempt on his life led to Capone foolishly entrusting his ledgers to Malone, who used them to bust him for tax evasion. While Van Alden's death ultimately served a greater purpose and resulted in Capone's arrest, it seemed too abrupt and sudden for a character who had survived every season.
Fitting Ending: Richard Harrow
Veteran Richard Harrow became an unwavering friend to Jimmy Darmody in Season 1, acting as his loyal bodyguard and muscle. The sharpshooter skills he acquired while fighting overseas in WWI came at great cost to his pride and appearance, and the disfigured war hero became a fan favorite with his deep character development and narrative complexity.
Though many fans wanted Richard to have the happy ending described in his scrapbook, the tragic hero inevitably required a tragic ending. He was shot after accidentally killing Chalky White's daughter, Maybelle, who stepped in front of his intended target, Dr. Valentine Narcisse. Actor Jack Huston respected his character's ending, describing it as "beautiful", and believed that Richard ultimately achieved the life he wanted.
Deserved Better: Chalky White
A racketeer, bootlegger, and friend to Nucky Thompson, Chalky White also had the distinction of being able to assemble and influence the Black community in Atlantic City. Eventually, Chalky got ousted by the likes of Dr. Valentine Narcisse and New York gangsters like Gyp Rosetti, forcing him to flee Atlantic City and temporarily forfeit his territories.
He was able to gain a foothold again with the help of Nucky and Al Capone, albeit after suffering much personal hardship, including the loss of his beloved daughter. Brokering a deal with Dr. Narcisse ultimately proved his undoing, because while Narcisse survived to the puzzling end of the series, Chalky's lapse in judgment resulted in a most disrespectful death.
Fitting Ending: Nucky Thompson
Nucky Thompson evaded categorization throughout the series. Even as a crimelord, he was equal parts cruel and comionate, and often favored diplomacy over violence. The writers concluded that the end of Nucky's story needed to come full circle, and the gangster needed to be killed by someone he knew. That person was Tommy Darmody, Jimmy Darmody's son, who pulled the trigger on Nucky in the final episode.
Tommy went under the alias Joe Harper, a kid looking for a job in Nucky's operation, whom the gangster took under his wing. According to the writers, Nucky needed to be "the cause of his own undoing", and while some fans felt his ending was predictable, it was nevertheless poetic justice.
Deserved Better: Owen Sleater
Bullish Irish enforcer Owen Sleater gained a reputation as a heavy for Nucky Thompson, but his roguish charms ended up catching the eye of Nucky's wife, Margaret. They embarked on a ionate affair that almost resulted in them running away together, but their plan was literally truncated when Owen's body wound up being shipped to the Thompson's doorstep in a box.
Fans felt that Owen's death was in poor form because not only did it happen off-screen, but it also involved a hefty suspension of disbelief in Owen's character to be achieved. Ordinarily cunning and resourceful, he dropped his guard and didn't follow his own rules when tailing a victim, a poor judgment call that ended up getting him killed and make him look unnecessarily callow.