The Worst Acts of Betrayal on 'Boardwalk Empire' - Rolling Stone
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The Worst Acts of Betrayal on ‘Boardwalk Empire’

Get schooled on the HBO series’ most treacherous moments before the Season Three premiere on September 16th

The Worst Acts of Betrayal on 'Boardwalk Empire'

Macall B. Polay


If there was a drinking game based on the number of times the gangsters, molls and even law-enforcement officials betray one another on Boardwalk Empire, all the players would be drunk within the first 10 minutes. But it's the duplicity that keeps us coming back, and the past three seasons have provided a satisfying batch of deceit and intrigue out of Roaring Twenties Atlantic City. In anticipation of the HBO drama's season finale this weekend, here is a refresher on some of Enoch "Nucky" Thompson and Co.'s shadiest dealings to date.


By Sarene Leeds

Macall B. Polay

Nucky Thompson Seizes Control of Atlantic City (Revealed in Season One, Episode 12)

The vicious cycle of betrayal in the Boardwalk Empire universe began years before January 1920, when the pilot takes place. Sometime in the early 1910s, Nucky was merely the sheriff of Atlantic County, and his mentor, Commodore Louis Kaestner, was in charge. The two were caught rigging an election, but only the Commodore went to jail – with the understanding that he would resume his role as Atlantic City boss upon his release. Nucky, unwilling to give up the power and wealth his new position provided, went back on his word, leaving a bitter Commodore poised to stage a coup of his own in early 1921, at the start of the second season.

Macall B. Polay

Jimmy Darmody Has Sex With His Mother (Revealed in Season Two, Episode 11)

To cheat on your girlfriend hours after she drops the bombshell that you knocked her up is one thing, but to do it with your own mother is sinking to new lows that would make even the most dangerous gangster cringe. There was never any question that the relationship between Jimmy and his scandalously young showgirl mother, Gillian, was inappropriate. Whether it was the way she passionately wrapped her legs around her son, recently returned from the Great War, or casually mentioned to his wife, Angela, that when she would change baby Jimmy's diaper she would "kiss his little winky," Gillian's love for her child knew no boundaries. But it was during a flashback to 1916 where we found out how far the line had actually been crossed – when a drunken Gillian initiates incest with Princeton student Jimmy.


Jimmy Horns In on Another Chicago Gangster’s Turf (Season One, Episode Four)

It's a tough town, Chicago. People don't take kindly to a young upstart from Atlantic City coming in and taking away their bootlegging business, like Jimmy did with his new friend, Al Capone. As punishment, Jimmy and Al's rival, Charlie Sheridan, has one of his men slash the face of Pearl, a prostitute Jimmy had taken a liking to. Now permanently disfigured, Pearl's "career" is over, and despite Jimmy helping to nurse her back to health, the damage is done – and she puts a bullet in her head.


Nucky Blocks New Jersey Sen. Walter Edge’s Vice-Presidential Nomination (Season One, Episode Eight)

Politics has always been a dirty game, and no one knows how to play the game better than Nucky Thompson. While in Chicago for the Republican National Convention, Nucky gets wind of the fact that Sen. Edge has gone back on his word to fund new roads to Atlantic City – a business proposition intended to thickly line Nucky's pockets. So he does what any corrupt politician would do: He promises Warren G. Harding's campaign manager, Harry Daugherty, the full support of the New Jersey delegation in exchange for keeping Edge off the ballot. As with all underhanded dealings, Nucky's betrayal bites him in the ass the following season, with Edge blackmailing now-Attorney General Daugherty into hiring a prosecutor in Nucky's election-fraud case who could actually put the county treasurer in prison.


Nelson Van Alden Impregnates Lucy Danziger (Season One, Episode 10)

It took several months, but even straitlaced, self-flagellating Prohibition agent Nelson Van Alden succumbed to Atlantic City's wanton pleasures like whiskey and loose women. But it only took one night in heaven with Nucky's castoff mistress, Lucy Danziger, to throw a huge curve onto his straight-and-narrow path. Nelson's indiscretion comes a couple of episodes after he heartlessly insists to his barren and miserable wife, Rose, that she not seek medical attention and instead trust in God to bring them a child. In Season Two, Rose, still infertile, learns of her husband's illicit affair and illegitimate daughter when she pays him an unexpected visit. Despite Van Alden's protestations that he planned to bring the baby, Abigail, home to Rose to raise as her own, she abruptly files for a divorce, no longer able to trust her secretive and philandering husband.


Angela Tries to Kidnap Jimmy’s Son (Season One, Episode 11)

It's not like Jimmy has been the portrait of fidelity since first meeting Princeton waitress Angela Ianotti, but she's hardly been a saint, either. Throughout both seasons, Angela has grappled with her budding bisexuality, seeking comfort in the arms of girlfriends in her common-law (and eventually, legal) husband's absence. Toward the end of Season One, Angela, uncomfortable with societal restrictions and dreaming of a more bohemian lifestyle for herself and her son Tommy, attempts to escape to Paris with her lover, Mary Dittrich. The plan is thwarted when Mary absconds without her. A shamed Angela, with nowhere else to go, returns home to Jimmy. Their future remains ambiguous until Season Two, when it's revealed that Tommy's parents have reluctantly married.

Macall B. Polay

Eli Thompson Joins Forces with Jimmy and the Commodore (Season One, Episode 12)

A product of sheer nepotism, Eli opened the series as the confidant of his older brother, Nucky, who installed him as Atlantic County sheriff. But as the first season progressed, Eli grew tired of his brother's manipulations and empty promises. At the end of Season One, as Jimmy and his father, the Commodore, begin hatching a plot to overthrow Nucky from his gilded throne, they are joined by a third party – Eli. Although Eli emerges alive at the end of Season Two – his fellow conspirators are not so lucky – Nucky, disheartened by his brother's betrayal ("Et tu, Eli?") doesn't let him get away without punishment. Eli is made to take the fall for Nucky's election-fraud case, guaranteeing he will serve prison time.

Macall B. Polay

The Commodore Fingers Nucky in an Election-Fraud Scheme (Season Two, Episode One)

Never underestimate the power of an angry old man. The main story line of Boardwalk Empire Season Two saw Nucky going up against three people who were once his closest allies: his erstwhile mentor, his former protégé and his brother. Still smarting over Nucky's betrayal years earlier, the septuagenarian Commodore discovered willing partners in his son, Jimmy, and Eli Thompson. By the end of the season premiere, Nucky was under arrest for election fraud, harkening back to the same charge that sent the Commodore to jail in the previous decade. Nucky's prison time only lasts until the next episode, when he learns most of his ward bosses have defected to the Commodore's side. But the nefarious plan is already unraveling by the fourth episode – Nucky's actual culpability in rigging Mayor Edward Bader's election notwithstanding – as Kaestner is incapacitated by a massive stroke.

Macall B. Polay

Herman Kaufman Is Discovered as a Spy for Manny Horvitz’s Rival Waxey Gordon (Season Two, Episode Six)

One of the more gruesome killings on Boardwalk Empire occurred when Jimmy caught Herman Kaufman double-crossing his associate, Philadelphia butcher Manny Horvitz. After informing Horvitz of Kaufman's deception, Jimmy arrives at the butcher shop to find a new addition to the meat selection strung up by his feet. The kosher Horvitz proclaims Kaufman to be treif (because he's also injured); therefore he is forbidden to carry out the execution himself. Jimmy is awarded the task instead. He initially hesitates, but quickly changes his mind when Horvitz suggests he's squeamish. Tired of Horvitz viewing him as a man without balls, Jimmy deftly slices the traitorous Kaufman's throat, thus putting to rest any doubts that he's someone to be reckoned with.

Patrick Harbron

Jimmy Orders Nucky’s Assassination (Season Two, Episode Seven)

He remained alive for five more episodes, but Jimmy Darmody signed his death warrant back in "Peg of Old" when, after goading from Eli, Al Capone, Lucky Luciano and Meyer Lansky, he gave the order to have his surrogate father killed during an event at Babette's Supper Club. Throughout the episode, it was clear that Jimmy regretted it, but his desire to be an important man in Atlantic City ultimately trumped his doing the right thing. Just before the hit man approaches Nucky, Jimmy walks up to the county treasurer in a weak attempt to justify his position: "It doesn't matter if you're right or wrong – you just have to make a decision." Nucky survives the shooting, the bullet only injuring his hand. But his relationship with Jimmy is irrevocably destroyed.

Macall B. Polay

Margaret Schroeder Sleeps With Owen Sleater (Season Two, Episode Seven)

When one thinks of Nucky Thompson, the words "manipulative," "duplicitous," "cunning" and "greedy" certainly come to mind. "Adulterer"? Not so much. Sure, he's had a couple of topless women in his lap since bringing Irish widow Margaret Schroeder into his fold, but the one thing he hasn't done is flat-out cheated on his live-in mistress. That's why it's a little hard to support Margaret's decision to have a sunset tryst with her benefactor's IRA-connected bodyguard. Still, the lack of chemistry between Margaret and Nucky was starting to get tiresome, and the sexual tension with Owen at least managed to heat up the Thompson household, even if the person finally bringing Margaret to orgasm wasn't named Enoch.

Macall B. Polay

Owen Turns a Blind Eye to John McGarrigle’s Murder (Season Two, Episode Nine)

His alcohol supply cut off thanks to the Commodore and Jimmy's machinations, Nucky is forced to journey to Belfast to pitch an exchange of machine guns for whiskey to Irish Republican Army leader John McGarrigle. Unfortunately for Nucky, McGarrigle wishes to take steps toward peace, rendering the deal a failure. As Nucky and Owen drive away with another IRA official, Bill Neilan, McGarrigle is shot by his own men. Neilan then agrees to Nucky's weapons-for-whiskey trade, ensuring that Atlantic City remains wet – and that the violence in Ireland continues. While Owen laments the death of his former boss, he disagreed with his decision take the pacifist route, and he admits to Nucky that even though he knew of McGarrigle's fate beforehand, any intervention on his part would have been futile.

Macall B. Polay

Jimmy Reneges on His Deal With Manny Horvitz (Season Two, Episode 10)

It's always a good idea to settle your debts upfront – especially when you're in business with a menacing butcher who's handy with not just a knife, but a gun as well. Between Jimmy's inability to deliver a shipment of alcohol (courtesy of a distillery bombing made possible by Owen Sleater) that Horvitz already paid for and Horvitz mistakenly believing that Jimmy put a hit on him, the Philly meat vendor is ready to take out the Atlantic City "boychick" by the end of episode 10. But the one who pays for Jimmy's shady and sloppy business is his wife, Angela. Horvitz, arriving at the Darmodys' home intent on killing Jimmy – who's heading toward Princeton to unload George Remus' medicinal liquor – settles instead for Angela and her lover, the beach-matron-flouting Louise.

14. Nucky kills his surrogate son, Jimmy (Season Two, Episode 12)


Nucky Kills Jimmy (Season Two, Episode 12)

Under the ruse of having captured Manny Horvitz, Nucky lures Jimmy to the Atlantic City War Memorial on a dark, rain-swept evening. But when Jimmy arrives, the Great War veteran knows that the time remaining in his life can be measured in minutes. All of the amends Jimmy tried to make throughout the episode wound up being for naught, because Nucky was unable to forgive his former protégé for turning against him. But as Nucky betrays the man whom he treated like his own son by shooting him twice in the head, he confirms the truth he had been dodging since the series' pilot, when Jimmy told him, “You can't be half a gangster.” The murder of Jimmy by Nucky's own hand signals a new era of Boardwalk Empire: Nucky Thompson has now betrayed himself, his associates and his loved ones by morphing into a cold-blooded killer.

15. Margaret gives Nucky's land away to the church. (Season Two, Episode 12)

Macall B. Polay

Margaret Gives Nucky’s Land Away to the Church (Season Two, Episode 12)

Margaret's decision to shack up with Nucky back in Season One was both contemptible and understandable. He was responsible for the death of her abusive husband, yet he provided comfort and security for Margaret and her children during a time when women had limited options. But Margaret's pact with the devil continued to weigh heavily on her conscience even as she reaped the benefits of her newfound wealth and power. When her daughter, Emily, was stricken with polio, Margaret saw it as a punishment for her sinful ways. Desperate to settle her debt with God, Margaret – Nucky's wife at this point – signs over the deed to a large portion of land her husband had given to her for safekeeping during his election-fraud scandal to St. Finbar's Church. Her decision effectively ruins Nucky's intended lucrative deal for additional roads to Atlantic City – and, most likely, her brand-new marriage.


Gillian Drowns Her Jimmy-Lookalike Lover (Season Three, Episode Seven)

For the first several episodes of the third season, it was unclear how much Gillian knew about the fate of her absent son. The fact that she was signing his name on checks and writing letters to her beloved "James" suggested the possibility that Nucky had covered up Jimmy's murder so well that even Gillian remained ignorant of the truth. But as time wore on, and her debts increased, it became evident that the Artemis Club madam was merely refusing to let go of the past. Once her financial situation became untenable, she reluctantly agreed to accept her son's death in order to lay claim to the house and holdings of the Commodore's estate. To do that, Gillian needed a body, and it came in the form of her unsuspecting boy toy, a Jimmy doppelgänger named Roger McAllister. After providing Roger with a magical Easter afternoon of feasting and fucking, Gillian lured him into a sumptuous marble bathtub, injected him with a near-lethal dose of heroin, and gingerly slipped him underwater until his body went limp.  


Gillian Tips Off Gyp Rosetti to Nucky’s Dinner at Babette’s (Season Three, Episode Eight)

Once Gillian acknowledged her son's death, her anger was at full throttle. An early scene in this episode established that Gillian knew all along that Nucky was responsible for Jimmy's murder, so it's almost organic the way she casually mentioned to Gyp Rosetti – Nucky's latest rival – where her son's killer would be dining one evening. The result of this disclosure is one of the most deadly incidents in Boardwalk's three seasons: a Michael Bay-caliber explosion at Babette's Supper Club claimed the life of Nucky's flapper mistress, Billie Kent, which galvanized the Atlantic City gangster to launch an all-out war against Gyp and his high-powered Sicilian backer, Joe Masseria. 

Macall Polay

Luciano and Lansky Warn Masseria That Nucky Has Put a Hit on Him (Season Three, Episode Ten)

What better way to avoid getting bumped off than to owe a huge debt to one of the most dangerous gangsters in New York? This is the tactic taken by up-and-coming mobsters Charles "Lucky" Luciano and Meyer Lansky, who persuade Joe Masseria to purchase a large quantity of heroin (that they will sell) in exchange for the heads up that Nucky is planning to assassinate the Italian mob boss. The repercussions of their decision are far-reaching though, as Nucky's hit man, Owen Sleater, is killed during the botched murder attempt. When a crate carrying Owen's dead body is delivered to the Ritz-Carlton, Nucky doesn't just receive a message to watch his back: Margaret's shattered reaction reveals that she and Owen had been carrying on an affair. Owen's death summarily quashed Margaret's plan to escape her wretched marriage – pushing her farther down a hellhole of her own making, as she's pregnant with her lover's child. 


Nucky Fingers Arnold Rothstein to the Feds (Season Three, Episode Twelve)

Arnold Rothstein may have class, sophistication and a knack for beating the odds, but the one thing he doesn't have is political connections. The professional gambler effectively destroyed his relationship with Nucky back in episode nine when he refused to help his Atlantic City associate kill Gyp and Joe Masseria. But it's Nucky who wound up having the last laugh in the season finale. After tempting Rothstein with control of the Overholt distillery (previously belonging to Treasury Secretary Andrew Mellon) – and succeeding in this deception – Nucky alerts Mellon that a known criminal is now operating his business. In a brief scene, Mellon telephoned Assistant U.S. Attorney Esther Randolph and ordered her to shut down Overholt's operations as well as arrest Rothstein.  


Tonino Sandrelli Murders Gyp (Season Three, Episode Twelve)

Talk about stabbing someone in the back – literally. One of the last few men remaining loyal to sadistic gangster Gyp Rosetti, Tonino Sandrelli is discovered hiding out at the Artemis Club by Nucky and Eli, who have taken their city back from Gyp's unstable clutches. When Tonino meets up with Gyp at the beach the next morning, he listens to his employer talk about moving their operations out west. But as Gyp takes a long, relaxing piss, singing the 1920s tune "Barney Google With the Goo-Goo Googly Eyes," he stops mid-lyric, as Tonino plunges a knife in his back. As Gyp turns around, Tonino finishes him off with a stab to the chest. When the deed is done, Tonino walks up the road to a waiting Nucky and Eli. Turns out Nucky spared Tonino's life only if he promised to take out Gyp – and to never show his face in Atlantic City again.

In This Article: Boardwalk Empire, HBO

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