Why did Deborah start a relationship with Bailey?

It’s definitely a pipe dream. Deborah doesn’t agree after 1933. It’s hard when you are young to visualize someone you are crazy about getting old so Noodles couldn’t visualize it like he did for everyone else. Also Max was a known figure. Photos of him had to exist so how could Noodles have not ever seen a photo of Max after he allegedly died? All Max did was change his name not his appearance. There’s no way he just changed his name and nobody else realized it including Moe. Just done major government official who happens to look like an older version of Max? So it has to be a pipe dream and the movie ends in the opium den.

It's all a dream...so there's no real answer. I agree with Max's latent homosexuality in way... It's all Noodles making up a 'happy' ending for everyone - so to speak. He died in the opium den. The Hoods got him and killed him. Everything right before the old man hands him a drink, that's the end of the movie - and everything after is an opium dream.

Of course Deborah knew who Bailey, her life partner, was. In the dressing room she told noodles

Don't go back to that door and open it, rather go out the other way through the other exit door, otherwise you'll be transformed into a statue of salt.

She was referring to the biblical scene. Lot's wife, as they all grew up in a religious Jewish environment when they were kids (especially her). She told him that because she knew exactly Noodles would recognize Senator Bailey's son, David (names after Noodles), as looking just the same as Max when they were kids. Noodles would realize he'd been betrayed by both, Deborah and Max, like hardly anyone could be in his life.

Deborah knew how this would devastate Noodles, felt ashamed and disgusted by herself (finally...) and literally begged and pled Noodles several times not to go back to that door and open it.

Now we are old, and all we have are our memories. If you open that door, you won't even have your memories anymore.

A young man's voice calling "Mama" could be heard behind the door. Of course did Noodles open the door and see the young man looking exactly like Max when he was a kid. She said,

This is Senator Bailey's son. His name is David.

The simple answer is that she needed a patron to allow her to act. Max had the money she needed to live the lifestyle she wanted. Max would exchange the money for sex. The son was probably a mistake. Neither of them wanted to disrupt their life, so they told the kid his mother died at childbirth. Remember when he knocks on her door he doesn't call her Mom. She's just a close friend of his Father.

The more complex answer is that everything that happens after Noodles informs on Max to prevent them all getting killed robbing the Federal Reserve is a dream in Noddles's mind. Leone planned this film for years near the end of his life. He wanted to create a film that was layered and would require multiple viewings to understand and appreciate. So you have to view the film as factual until Noodles goes to the opium den to escape the reality that he killed his friends. All the childhood scenes are used to tell us who the characters are and what motivates them. The scenes in the 60s are all Noodles on opium and how his mind tries to make sense of things. Max would have taken the money, hooked up with the unions, gotten rich, gone into politics, gotten old and eventually into trouble. Deborah would have done what she needed to do to become the famous actress she dreamed of being. She hooks up with Max because that is all Noodles knows. She is a poor kid who will need money and Max will be the money man. In his mind there's not a huge world with many characters and unlimited possibilities. There's only the people he knows at the time he is smoking the opium. Even the son of Max and Deborah is played by the same actor who played the role of Max as a teenager. Noodles looks dignified in his dream. He goes back to Deborah and she is calm and nice to him even though he raped her. She still looks young and beautiful, but every other recurring character has grey hair and is older looking.

There are so many details that could be understood as just part of the story told chronologically in a straight forward manner. However, they make more sense and tell a different story when analyzed as part of Noodles trying to reconcile what he knows happened with how he views himself. Why did Max attack him? The straight forward version as told by Carol is that Max wanted to go out in a blaze of glory so he shot it out with the Feds and they all died. In Noodles's dream, Max conspired to fake his death so he could reinvent himself into a great and wealthy man. In the end, Max wants Noodles to kill him and get revenge for ruining his life. Noodles views himself as loyal and the better man so he refuses to even call him Max let alone kill him.

There are many layers to this movie once you view it as Sergio Leone's idea of how these people at this time in America would behave in the circumstances he created. He gives us a clue that what we experienced on first viewing the film was not the whole truth. He ends with Noodles in 1933 smiling after taking hits of opium to let us know it was a dream. Now go back with that in mind and watch the movie again, and again!

The real answer lies in admitting to yourself that it doesn't make any sense that Deborah would end up with Max.

It lies in the interactions between Noodles and Deborah in the dressing room, in seeing the way the scene is framed (through a mirror, with her makeup on). The last time Noodles was with Deborah before, he was raping her. The exchange between them in the dressing room is fitting of a man that doesn't even really grasp what he had done to her, only that he is still pining after her in a way and has to come to terms with never being with her.

The hints to the movie itself (aside this question about Deborah).... lie in the anachronisms and the especially surreal moments that you witness in the scenes in and around Bailey's mansion.

I really don't like giving a blunt answer to movies like this one....but there's definitely some parts of this movie that should be raising some red flags.

Deborah loves Max's power and the possibilities as Mr. Bailey to advance in her career by being with him, when they met later after he betrayed and murdered his friends. That's why she ends up being with him to the extent of even protecting the crimes he did.

She is narcissistic and the love for Mr. Bailey is a narcissistic one. She may love Noodles, but her narcisstic impulses are stronger and since they had similar characters, this relationship had to work correspondingly.

It has become obvious to me after watching this movie many many times over and it's actually a very very very depressing take on life which makes it one of my favorite movies.

Deborah had lost interest for Noodles as a youth and entirely after he had raped her. In addition to that Max had been in competition for Noodles every score and position since the get go, from scores, sloppy seconds, cockblocking his Deborah. After his final mastermind plan of cutting all loose ends even his own identity by "dumping" Noodles making him turn on his friends and ultimately himself having hit out on Noodles his girl and Moe. Bagging Deborah was only cherry. He even admits the whole thing was a syndicate sting operation having his own body identified and living in Noodles' place...

Deborah probably had no involvement in this but Noodles' comparison of her to Max made an impression and that much more sweet and bitter betrayal for the both. Even naming their child DAVID. Deborah was always a good tease but her acting was always forced. And till the end she could not acknowledge her betrayal for the sake of memory. Maybe why Noodles never killed Max or Baily in the end. His memory betrayed HIM in the end. Making his integrity the prevailing SCORE of his destiny. Also the final image cut makes it Noodles' LAST laugh out of the betrayal.

The "Look at yourself Noodles" scene is to me highly important, remember Noodles going and looking at himself in the mirror right after Deborah's humiliating comment. Deborah has dreams and ambitions, nowadays she will be called a Social Climber and that's clearly something that make her closer to Max: a sharp, bright, dominant but pertubated personality.

Max and Deborah had one thing in common, they were both in love with Noodles. Max always slept with the women that Noodles had had first. Max's feelings towards Noodles were pseudo-homosexual, no doubt about it. Max takes as his mistress Noodles' first 'rape' victim, Carol. And then years later he gets together with the love of Noddles' life, Deborah, who is also one of Noodles rape victims, but more of that later. Max is able to feel sexually close to Noodles by having sex with the women that Noodles has had sex with first (forced or otherwise). This is the closest thing to physical intimacy with Noodles that Max will ever get.

Noodles loves both Deborah and Max, but he feels more of a sense of loyalty to Max and this is why he always chooses to stand by Max, even at the expense of Deborah. Twice in this film, both as a child and an adult, Deborah taunts Noodles with the words "Mama's calling.", meaning that Max wants Noodles at his side. Deborah is hurt that Noodles always chooses Max over her, and ultimately this is the REAL reason that she decides to follow her ambition and go to Chicago, she is angry and upset that SHE is not number one in Noodles loyalties and priorities, Max is and Deborah feels that she will always be competing with Max for the attention of Noodles. This is also the reason that Deborah and Max have never liked each other, they both love Noodles and there is a deep jealousy between them, because they BOTH want Noodles.

Max of course can never reveal to Noodles how he really feels about him, perhaps Max does not even realise himself that what he feels for Noodles is sexual love. This is the reason that utimately, Max and Deborah get together later in life, their shared love of Noodles is what draws them together, and keeps them together, despite the fact that they previously did not like each other. By being together it is as if they can keep alive their memories of Noodles and the deep love that they still both feel for him.

As for Noodles, he is a much simpler character (at least he is, compared to Deborah and Max). Noodles is a thug, plain and simple. When he makes his fortune, he believes that this will convince Deborah to marry him and MAYBE she would have if he had been prepared to choose HER instead of Max and the gangster life-style; but Noodles is not a hugely intelligent individual and he blows his chance with Deborah by not putting her first.

He takes her on a date, and in the back of a limousine, Deborah tells Noodles she is going to Chicago in search of stardom. Noodles is devastated, crushed. He has loved this girl since he was a kid, and finally, just when he thought she was within his reach, he is going to lose her again. He is so deeply hurt, and so angry that his love is going to be leaving him, probably forever, that for a moment he is in the grip of some kind of madness. Deborah is startled. She has never felt such anger and coldness from Noodles, and she doesn't like it, she wants them to part as friends so she leans in and gently kisses him. This is too much for Noodles, he is getting mixed signals from Deborah (he believes). First she is rejecting him, and then she is kissing him. Noodles is confused......does Deborah want him to make love to her?

Now remember, Noodles is not very intelligent, and he has been brought up with absolutely no idea of how to treat women. He has spent his most formative years in a borstal and a prison, and he himself committed an act of murder when he was little more than a child. His experiences with women have been limited to prostitutes or with women like Carol, the blonde cashier who encouraged him to rape her because she is a masochist who enjoys extremely rough sex; the scene in which Carol entices and provokes Noodles in to raping her ends with her having a screaming orgasm. So now we have Noodles in the back of a Limo with the pure and innocent Deborah, and he is thinking that she is 'asking for it' as well.....and so he rapes her in the most brutal and horrific fashion. But he discovers that Deborah is most certainly not like Carol, or the young prostitute Peggy, Deborah is definitely NOT ejoying what is happening, Deborah is certainly screaming, but not with pleasure. Noodles is genuinely puzzled by Debbie's 'strange' reaction, and this is why he carries on with the ghastly rape, he figures that if he 'keeps going' and 'gives her a bit more' she will start to enjoy it like Carol did, poor, ignorant, foolish Noodles.

Only later does he realise that he has ruined whatever chance he ever had with the love of his life by this one revolting and despicable act. For her part, Deborah moves on with her life, but there is a part of her that will never stop loving him because she also realises, deep down, that Noodles has suffered more from the act of raping her than she herself has. Noodles life was in ruins from the moment he raped Deborah, and he was never truly happy again. He had hurt and violated the one person that he loved more than anyone else in the world and this is the reason that Deborah is very easy on him when he turns up in her dressing room all those years later, she doesn't scream or rage at him because she knows he has already suffered a life sentence of regret for what he did to her and she has finally forgiven him.

As for Max, he has wealth, fame, position, he has Deborah and they have a son together named David, who is undoubtedly named after Noodles, whose real name is of course David Aaronson. And yet, Max is not happy. How can he be, when he betrayed the only person he has ever deeply and truly loved? His friend and the love of his life, Noodles. This is the reason Max wants Noodles to kill him, it is his way of saying to Noodles, you can kill me for what I did to you but please forgive me first.

First, consider Max’s motivation in snagging Deborah. Throughout the film, Max is driven to sexually possess the women Noodles has already had. During their initiation into the world of sex, Max insists that Noodles take Peggy first. Years later, Max takes the woman Noodles raped, Carol, as his lover. He even asks the prostitute in the hearse who gives Noodles “a roll” if she wants “a little pick me up.” Whether this indicates Max’s latent homosexuality (quite possible considering he constantly refers to sodomy in his language, including during an early exchange with Noodles: “Drop your pants and I’ll stick it to you again.”) or merely stems from macho competition is open to interpretation, but one thing is clear: Max desires Noodles’ women. And possessing Deborah, Noodles’ life-long romantic ideal, would be Max’s crowning achievement. He must have her and will go to any length necessary to make it happen.

Deborah might have been receptive to Max’s initial advances partly out of revenge against Noodles for raping her. But more importantly, Max, unlike Noodles, is the kind of man Deborah would respect. He may have started out as a poor immigrant, but, unlike Noodles, he is a man of ambition with big plans for himself. Max reinvents himself, literally assuming a new identity, and becomes just the kind of successful, upwardly mobile type that would attract Deborah. Noodles himself points out the similarity of the pair when he complains to Deborah, “You’s twos are just alike – that’s why you hate each other so much.” Deborah and Max, for all their apparent antipathy, share the same values for wealth and fame – in Deborah’s words “making it to the top.” By contrast, Noodles is a self-described loser whose lack of ambition is held in contempt by both Deborah (“you’ll always be a two-bit punk”) and Max (“You’ll carry the stink of the streets for the rest of your life”).

Just as Deborah is willing to give up the one person she’s ever loved to pursue her dreams of stardom, so Max is willing to sacrifice his boyhood friends to facilitate his own ascendancy. Both Max and Deborah, who is portrayed as narcissistic prima Donna, are willing to do whatever it takes to “get to the top.”

Plus, the fairy-tale world Leone creates is so self-contained and hermetically sealed that the central characters barely interact with anyone other than each other and those immediately associated with them. In this context, who else was Deborah going to end up with?

I don't think there is a real answer in terms of the character, and I suppose we could imagine many scenarios since the "romance" occurred entirely offscreen. I think that it is beside the point, in terms of the writers of the film, what Deborah wants or what her point of view is. She was the hope of escape for Noodles, she was only important in terms of what she symbolized for him. His rape of her was his damnation. And the only reason she is married to Max in the future is to add tragedy and pathos to the betrayal of Noodles by Max.

The entire "old age" segment of the film has an eerie dreamlike quality, and I'm not sure it is supposed to seem realistic. Of course, there is the famous "it was an opium dream" theory supported by the fact that the movie ends on Noodles in the opium den in the past. One should also note that while Max and Noodles (and other characters) look noticably older, Deborah looks unchanged from 30 years before. I know this isn't an answer, but I think this storyline is more poetic and interpretive than something we are supposed to analyze from a character point of view.

Unfortunately, the reasons are never really explained. There are a few possibilities, but nothing definitive.

Firstly, it's possible that after Noodles rape of her, she simply lost respect for herself and her body and simply decided that material riches were all she needed. She chose to be with Max/Bailey and take the financial security and comfort that relationship brings - not all that surprising given her background.

A second possibility is that the rape had nothing to do with it and she was simply attracted to the money. This is certainly the opinion of the FAQ part of one of the movie's fansites, Once Upon a Time in America.net, which states:

Why would Deborah ever willingly hook up with Mr Bailey?

Mr Bailey is a multi millionaire, with valuable assets, a grand mansion and a son. I've no problem with this whatsoever. Deborah probably isn't madly in love with Bailey but as we get older other factors such as comfort and security become more important.

A third possibility I read in another article, which believed Deborah's motivations in the movie were always suspect:

As Max increasingly assimilates the values of capitalism however, his use of prostitution changes. He later uses his status as Secretary Bailey to acquire Deborah, in essence using wealth to "hoard" Noodles' girl where he previously would have "shared the wealth". This act also implies that Deborah, who has been built up as the "nice girl" in this film, really differs from a hooker like Peggy only in price.

Ultimately, there is no correct answer and we can only made educated guesses. It seems highly unlikely Deborah didn't know Max's true identity. However, I also don't like the idea of her being simply attracted to money, as I hoped for better from her character. Therefore, I like to believe in the first theory - although we'll never know the "real" answer.