What if Tommy married May instead of Grace?
He’d be miserable. The class stuff that goes on with them is 😬. Like. I think May developed some real feelings, but her interest in Tommy is mainly like… he’s an aesthetic conquest. She wanted to fuck the gangster she saw at the auction who she thought was “beautiful”, and right off the bat she framed her pursuit as bidding on him—as Tommy being a thing she can buy… specifically to be… bred. 🌚 The filly for her stud. Tommy knew this! He thought she was hot and her contacts could be useful (and like her he was also trying to get over somebody) so he was like yeah sure why not both of us can get laid. When he initially breaks up with her, she gets upset and he’s really confused about it because he knows he is an aesthetic conquest to her he did NOT think she took them seriously. And she indicates there are some real feelings (which is what keeps him interested), but her main explanation for why she is upset is that her staff and all the rich people she associates with know she’s sleeping with him and “they’re laying bets on when you’ll steal the silver” so if he leaves her, it will be embarrassing (and this part of her perspective visibly icks Tommy out). She is upset because it’ll look like she was used, when she was the one who was supposed to be using him. She also talks bitterly about how at the derby, it’ll be “backwards” with her down below with the horses and him up above. That’s “wrong” because he should always be beneath her. (And this is in a season where Tommy is repeatedly reminded by section D that his class and ethnicity places him beneath). Like. May plays it cool about how she can be normal about Tommy’s class (and there are DEFINITELY ethnic prejudices here too in the steal the silver line and elsewhere) but she is NOT able to be normal about it. There’s also her horse trainer very obviously having a problem with Tommy being gypsy and Tommy clocking that instantly and May is either oblivious or (worse) just thinks he should be “diplomatic” about it because well he IS gypsy and obviously that’s “bad” so he should just deal with it???😬
She later talks about how she will “win” him from Grace by buying him (via her racing contacts which are useful to his business). She is confident she can beat love with money which is also a commentary on what she thinks of Tommy (someone shallow and desperate for her wealth such that he can be bought). She jumps to money again later in season 4 when Lizzie gives her and Tommy a hard time, pulling out a blank check and telling Tommy to put down whatever amount he wants (and I think that also bothers Tommy actually because he knows what that signifies). Like this is what May does. (I might also mention her desire to rubberneck “a gambling den” like she’s doing poverty tourism and possibly showing up to rubberneck the season 4 gang war (which is why I think Tommy’s hot and cold on her presence even before the discussion in the gin distillery). I do think there’s a lot of small things about what May thinks RE: class that give Tommy the ick even though he also is into her (partly because he does have a thing for rich women at first, partly because May being so into him in of itself does something for him—he likes being desired). In a marriage the prejudice and lack of perspective would quickly take a toll. It is a lack of respect rooted in prejudice both class and ethnicity-wise however much May thinks she’s being normal she just can’t because this is just… what she believes and she can’t relate to him. She sees Tommy as her inferior. He’s fascinating and unlike anyone she’s ever met, but he is a thing she thinks she can buy (because why wouldn’t he choose her wealth and influence over love?) and someone who is supposed to sit below her or at the very least be raised through the ranks through her benevolent gifts (even as his ambition, criminality, and self-made success also actively intrigues her).