I do not claim to be an oracle of who will win the Tonys but here are my ideas, culled from a lot of time spent online reading hot takes and the smaller theater award winners, discussions with my two biggest theater friends who I have been discussing theater with for over 12 years, and also brief chatting with an acquittance who is Tony-nominated adjacent (one day, she will have her own instead of just getting mentioned in speeches!).
Here are what I think the odds are of "Hadestown" winning Tonys.
Best Musical
"Hadestown" has a really good chance of winning but it is by no means guaranteed. Mostly everyone thinks it's going to come down to "Hadestown" or "Tootsie." No one is talking about "Ain't Too Proud", "Beetlejuice" doesn't seem to be a viable candidate (described by my friend as fun but nothing to write home about), and "The Prom" seems to only be really endorsed by the New York Times writers who have an unreasonable amount of power when it comes to what goes to Broadway (they are why "Hadestown" got changed so much and why "Fortress of Solitude," the best musical you've never heard of, never went to Broadway) but not necessarily the deciding vote.
The thing here is really whether the voters want to go safe and traditional with "Tootsie" or new and unique with "Hadestown." In the past few years, they have definitely tended towards the new and unique, but they also have a clear bias against sung-through musicals (see 2017 when "Come From Away" won Best Director but lost Best Musical to "Dear Evan Hansen" in spite of doing really well at the smaller awards). "Hamilton" is a recent exception to this but "Hamilton" was an exception in so many ways.
Overall "Hadestown" is the better show. Both shows have issues with their books but "Tootsie" is tighter and also less interesting. And "Hadestown" has vastly better music. Personally, I'll be surprised if "Tootsie" wins but these kinds of things have happened before.
Best Director
Basically everyone seems to say it will be Rachel Chavkin even if they don't think "Hadestown" will win best musical, and this is very interesting to me as someone who knows a bit more about the interworkings of the Oscars than the Tonys. The Oscars have done this weird and possibly bad thing a lot over the last few years where they give Best Direction to the most artistic and interesting film but Best Picture to whatever movie they enjoyed the most. Last year this was painfully obvious with Alfonso Curon winning for his direction for "Roma" but "Green Book" winning Best Picture. The Tonys don't do this as they usually give both to the same show or they give direction to a revival that will then win Best Revival. But again, 2017 this changed.
That being said "Oklahoma!" seems like the only real competitor here and if Daniel Fish wins over Rachel, I'd be okay with it. "Oklahoma!" was a revelation (and better win Best Revival over "Kiss Me Kate").
Best Book
Here's one where I think "Hadestown" is likely to lose. First of all, the book of "Hadestown" is messy. I love "Hadestown," it's probably my favorite musical of all time, but the book is messy. There are places that are overexplained and a lot of imbalance in how the themes are woven into the story (while still being totally brillant but yeah). There are things that should have been fixed in all the transfers, but they weren't, and it started to feel a bit like writing wack-a-mole following this show since the New York Theatre Workshop.
Also a lot of people find "Hadestown" confusing, which is a problem, but I find this is often a problem of people not being good readers more than anything having to do with the show.
Additionally, Tony voters have no idea what the book is with a sung-through musical. Basically, they don't think there is one. Dialogue is only part of what makes the book, guys.
"Tootsie" will probably win instead. It's got a very tight script and is truthfully very funny. Even though there are as many oops-you-should-edit moments as in "Hadestown," the comedy and the appeal to the particular demographic they were shooting for will win it.
Best Original Score
I feel like "Hadestown" has this one locked down. Even people who find the show incomprehensible seem to love the music. David Yazbek won last year for "Band's Visit" (a vastly better show than "Tootsie") so it's safe to say he's out of the running. I've got nothing else here.
Best Orchestrations
"Hadestown" has a damn good chance here too. Its music is one of its strongest qualities, and if you compare the NYTW to the Broadway in terms of orchestration, there's a lot going on here and it's all good. "Oklahoma!" is a potential opponent because of how they managed to change around the original to make it all read so much better to a modern audience.
Best Performance By An Actress In A Leading Role
I'm going to say Eva has only a 25% chance of winning. Stephanie J. Block seems to be a likely winner because of her previous nominations and the fact that the Tonys often give out awards for career work instead of the single show they are in. Otherwise, "The Cher Show." Really. Some people think Kelli O'Hara has a chance because the Tony voters love their generic starlets but since she's already got a Tony, I think Stephanie and Eva are much more likely competitors. "The Prom" girls seem to cancel each other out (more on the canceling effect two categories below).
If Eva wins I will be PUMPED, but I'm not counting on it.
Best Performance By An Actress In A Featured Role
Everything here comes down to Amber Gray versus Ali Stoker. The "Tootsie" actresses cancel each other out (more on the canceling effect one category below), but Ali is far and away a standout over Mary Testa. To quote my acquaintance, "Amber Gray will win because she's the most interesting woman on Broadway, like how Katrina Lenk won last year." I think she could be right here, but I will propose an additional theory for why Amber may win: Amber originated a role, one she has been working on for years. Ali stole the show in "Oklahoma!" but she stole the show with a classic show stealing role. Also, because those voters like career work, Amber has been around longer (although she wasn't nominated, she was the best thing about "Natasha Pierre" for me). Ali is young and at this point mostly known for her small role in Deaf West's "Spring Awakening."
Ali will be a Tony winner. Maybe this Sunday. Maybe in a few years. If she wins I'll be happy for her and there's no denying she will deserve the award, but I'm rooting for Amber.
Best Performance By An Actor In A Featured Role
I have gone on a journey with this category. Let me start by saying it seems like Andre DeShields will win. Now let me back up and tell you the long adventure I went on to conclude this.
I have now mentioned "canceling out" a lot, which has a tendency to happen with shows where multiple people are nominated (usually in acting). The important thing to note is that just because two people are in the same category does not mean they automatically cancel each other. Daveed Diggs won for featured actor for "Hamilton" over his costars Chris Jackson and Jon Groff, and there's a clear reason why: of the three he was the standout. He was the most dynamic and had the meatiest role. This only works when there isn't an obvious winner in that show. And this is why figuring out this category has been so damn difficult and I still may be wrong.
Originally one of my friends said he thought Andre and Patrick Page would cancel each other out and that the two guys nominated for "Ain't Too Proud" would cancel each other out and we would have the award going to the guy from "Tootsie" (sorry I don't have the names, but for the reference that guy was literally my favorite thing about "Tootsie"). I initally argued that while both "Hadestown" guys do clearly dominate the category in general, Patrick could win because he plays a dynamic character while Andre plays a static one. My friend countered that the Tony voters really love narrator characters, and well, he's right. This idea was expanded by my other friend who pointed out that Andre opens and closes the show and has a lot of the theme-dropping lines, while Patrick doesn't make his entrance until halfway through Act One and that this leaves an impression.
But ultimately it probably comes down to this: career. Andre will get the award because of his career. Every middle aged gay man I've spoken to who didn't understand the show was very proud to tell me that they saw him in "Ain't Misbehavin" in the 70s (to which I said I saw him in "Fortress of Solitude" a few years ago as a jest that none of them seemed to be amused by).
The canceling theory may still play here, but it's hard for me to imagine that the award won't at least go to one of the "Hadestown" guys.
Best Scenic Design, Best Costume Design, Best Choreography
I'm talking about these three together because my explanation for all three is basically the same. In all three of these categories, "Hadestown" feels like an underdog because it is not flashy in the way shows like "Beetlejuice" or "King Kong" are. They don't have the grandiosity or diversity of costumes of "The Cher Show" or the traditional choreography of "Tootsie."
But "Hadestown" is literally creating a time and place that doesn't really exist; it's not even fantasy, just otherworldliness. The scenic design and costumes anchor you in a place that is like our world but isn't and everything about the choices made, from the shifting set to the details of the costumes, is meant to create this place of kinda New Orleans, kinda 1930s, but also kinda anywhere and now. If "Hadestown" wins scenic design or costume design it will be very deserved and very unconventional.
The choreography has a similar effect. The only real 'dance' numbers are "Living It Up On Top" which is very traditional, "Way Down Hadestown" which feels more frenetic and unplanned, and "Lover's Desire" which is literally a slow dance. The thing is, the choreography throughout the show tells you so much about characters, what they are thinking, and how they are feeling in a way traditional choreography doesn't. Interesting enough Amber Gray was nominated for a dance award for the show. Like with scenic design and costume design, if "Hadestown" wins it will be deserved but a bit uexpected.
Best Lighting Design
Those "Wait For Me" lights will probably win them this Tony but it's worth acknowledging that this show has a lot of amazing lighting design from those swinging lights to the lanterns the Fates use to how Eurydice is able to disappear with the use of light, smoke, and turntable, to the lights of Hadestown, to those colored lights in "How Long" that I am now weirdly obsessed with. But those swinging lights are so iconic that they just might win it on that alone.
Best Sound Design
I know nothing about sound design and no one else seems to either. I noticed some sound design. I also noticed some sound design in "Oklahoma!" I don't know anyone who saw "King Kong" or "Ain't Too Proud." Who knows.
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