Do you ever think Tommy truly loved Grace? Or do you think he married her because she got pregnant and he felt it was the right thing to do? Loved her bc she was the mother of his child and felt he had a duty to her? I get very torn on it bc while he seems like he’s “happy”, I just can’t get over how hurt and upset he was when he realized the depth of her betrayal in s1. And how he reacted when she told him about the baby initially was not one of being in love imo but he was ambushed with the news at the worst possible time lol so I get that angle, too.
I feel like if she hadn’t died their relationship would’ve ended much like his and Lizzie’s did. I think the guilt really wore at him… and then people tend to make their deceased loved ones into a saint after they’re gone, and overlook the negative qualities of them at times
I have no doubt at all that Tommy loved Grace. He says so, first of all, but even if he hadn't, it would still be apparent imo from the way he is about her in 2x05 and other places.
I think when she showed up at the derby he was just very overwhelmed. He hadn't expected her to be at the derby at all, then she was randomly there and telling him she was pregnant and that she loved him. He was actually flirting with the idea of continuing something with May before that, because he didn't think Grace would choose him. He was also in the middle of an assassination plot he'd been forced into, and he knew he might die that day. He'd been preparing for the possibility that he would die that day for weeks (maybe even months). He'd set up a trust for his nieces and nephews specifically because he had no children of his own, and now on a day he might die, Grace was telling him she was pregnant and the baby was his. So I think when he said "Make your husband believe the baby is his", what was flashing through his head at that point was "there is a very big possibility I die today, and the baby needs to be provided for and she needs to be provided for and I won't be here." This is also why he told her he would decide after the race—because he didn't know if he'd be coming back at all. It also wasn't until after that that she told him she loved him, and I also think he needed to hear that to decide.
Whether they would have lasted is something I do think about occasionally. It's very interesting to me that at the derby, Grace is confronted by May who basically throws in Grace's face that she and Tommy have slept together, and heavily implies that she can buy Tommy because she can lend him wealth and influence he needs to grow his business. Grace says "There's business and there's love," and May says "Is there?" And this DOES get to Grace very effectively, because for all the insecurities on Tommy's side, Grace had been hurt as well that Tommy chose his family and his business over her when she asked him to come with her to New York. So May saying "Business will ALWAYS come first" really got to her. It also got to her that Tommy didn't tell her about May (Grace explicitly asked him if he was seeing someone in 2x05 and he didn't tell her, and May used that to twist a knife that basically amounts to: "Tommy will lie to you and sleep with other people and you will always have to worry about that"). The insecurity Grace feels here must fester, because it is most certainly not resolved by season 3.
Right before Grace dies, she and Tommy are fighting because Grace clocks (imo a very one-sided) sexual tension between Tommy and Tatiana. She knows Tatiana and Tommy have some sort of business relationship, and she is 100% thinking of May Carleton and Tommy fucking her, and she immediately thinks Tommy must be cheating on her with Tatiana (even if it's just to get something). It is very possible that Tommy would have still fucked Tatiana had Grace not died, because he didn't really do it because he wanted to to begin with, and in fact, the second time they sleep together, it does pretty quickly turn into what really is a sexual assault. So while Grace's death arguably contributes to Tommy agreeing to sleep with Tatiana (Polly says about it, "You're grieving and when you grieve you make bad decisions") Grace is very clearly not okay with Tommy sleeping with other people under any circumstance, and that could... potentially be a problem, though Tommy's engagement in basically... whoring himself out doesn't become as overt until after Grace dies (May is really just dipping his toes into that sort of thing). We can definitely argue Tommy's use of his body in a sexual context to get things is exacerbated by her death because it is almost a self-harm behavior, and maybe he wouldn't have done some of the things (er... people) he did end up doing if she didn't die and he didn't blame himself for her death.
Besides sex, there's also just the simple fact that Tommy is involved in illegal activities. Grace wants Tommy out of the criminal aspects of his business entirely, but Tommy being able to leave behind the criminal aspects of the business is somewhat dubious, especially because what motivates him to continue the criminal aspects of the business is not just his incredible ambition, but increasingly a feeling that the illegal aspects of the business provide him with safety in a world that is stacked against him... and section D would be cementing those lessons for him in season 3 whether Grace had died or not. Section D also keeps Tommy within the illegal aspects of his business directly within the context of season 2 and 3 by forcing him to do things he finds deplorable like carrying out assassinations for them and committing acts of domestic terror, using threats to his family's safety to keep him in line. Charlie was specifically used to by Hughes to enforce Tommy's compliance, and motherly instincts coupled with the fact that Grace did initially leave at the end of season 1 in search of safety from criminal activity and committing her own acts of violence could very well push her to leave Tommy for Charlie's sake if nothing else.
So yeah. There are different directions to take things. But I do also kind of think Grace was running away from something in herself when she sought out that safe marriage in New York (I think @deadendtracks also has some meta on this somewhere?) and I could also see a canon divergence where Grace is able to make things work with Tommy by accepting parts of herself that she's scared of.
Lizzie and Tommy, coming from the same class background, find common ground on the illegal aspects of the business (as Lizzie says, "You don't get what you deserve, you get what you take") and even some common ground on Tommy sleeping with other people, though there are rules about when and where Tommy is allowed to do that. It isn't simply him sleeping with someone else that breaks their marriage, but the specific circumstances: they are grieving the loss of their daughter and their marriage is under significant strain and the person Tommy slept with is someone Lizzie and Tommy both find absolutely disgusting. It is another reminder that there is no limit to what Tommy won't force himself to do if he feels he has to, and while Tommy tries to contain the fallout to himself, the reality of the situation is that he can't and Lizzie shares part of any harm he puts himself through by then, both directly from the results of his actions hurting her as someone who loves him deeply, and indirectly as his engagement in self-harm worsens his mental illness and she is the person who is trying desperately to take care of him through that mental illness. But we can also argue that Tommy's delusions and the self-loathing and guilt and shame they are couched in starts with Grace and the cursed sapphire as the origin point for him thinking he is cursed, so if she never died, that also alters who Tommy would be later on. Like potentially everything up to and including how mentally ill he would be.