You may have overlooked Steadfast. Like, there you are furiously thumbing through Yelp reviews for local beef and burgundy joints because your senior partner just did you a solid and you want to take her out for a chop and some Chave but merde: The Loop. The prices. You’re just an associate. You drive a 2012 Kia. You’re not taking her to the Cut. But you definitely want that mood, that dark wood and quiet jazz vibe of a classic Chicago steakhouse for maybe a little less than your rent.

Go to Steadfast. Here’s why: they’re in a killer boutique hotel, the Kimpton Gray, they’ve got ambiance out the wazoo, their new menu rocks, and their sommelier knows her way around a good Sonoma Pinot. And a French Syrah. And good champagne.

But let’s talk about the barstools. I am an ample man. Ample in the sense that my southern hemisphere is August in its nature. My posterior is proportioned plentifully. I’m fat, alright? And most barstools are designed for people whose posteriors are apparently pointy, leaving me hanging halfway off or just standing there trying to look all nonchalant when the truth is I’m afraid the stool will stab me in my magnificence.

But as I walked up to the counter at Steadfast, a sparkling shaft of light shone down onto the stool at the bend in the bar and I realized it was Wisconsonian. Like an ottoman grew up big and strong. Not only could I comfortably park my caboose, there was still room. I could lay down and take a nap on this barstool. I could share it with a friend. I could build a tiny little house and move in and blog about it. Obviously, the 50/50 group who runs Steadfast knows their customer base in the Loop.

So does Daphne Stratta, their sommelier. I met with Stratta recently to talk about her wine program, sample a glass or two, and eat the last of their almost-award-winning chocolate dessert before their new menu goes online.

Yeah, the last one. I know you’re all like—but wait a minute, I love that dessert. I love Chocolate! It has a port ice cream that makes me cry and I’m right there with you, son, but what can I say? You should visit more. It was truly and magnificently and stunningly delicious with just exactly the right amount of chocolate to bear the name and to satisfy the promise of the premise, but not too much, not a Willy Wonka level of chocolate. It was just exactly right and the fact that I was still drinking a glass of Stoller Pinot while I almost licked the plate is a testament to Stratta’s genius in selecting wine because I would drink Stoller with everything from cheese curds to steak Diane and it would work.

Stratta is among the growing list of Sommeliers looking to break through the veil of terror that keeps a lot of diners from exploring a wine list or talking to their sommelier. She’s also part of the growing company of sommeliers using their buying powers to nudge Napa and Sonoma producers to look back to 1975 before their Cabernets and Pinots went crazy with the tannins and the alcohol and the hey hey hey.

I love a big fat red. It may be the gate through which I walked into the gardens of great wine, eventually making my way through all the punch-you-in-the-face Cabs and Zins to the mellower Burgundies and the Syrahs and the other wines in the back of the estates, wearing black dresses and tuxedoes and talking quietly among themselves, looking occasionally over at the Cali cabs who were making so much noise. I get why California took this detour because in the 80s and up until the late aughts, big wine was king. It still is. When you walk into a top dollar steakhouse these days the wine list is more like Fight Club than film noir. It’s not subtle. Neither is the wine.

I stuck my schnoz deep into a glass of Elizabeth Rose, Napa Valley, CA 2015 Pinot while Stratta told me it was a pinot and I thought, wait, I’m snorting the wrong wine. Where most pinots hit you with cherries and roses, the Elizabeth Rose apparently snuck into the barrel of a nearby Cab and stole its flavor profile. It’s like popping my head into my grandpa’s study when he’s smoking a pipe full of dark cherry tobacco. There’s leather and tobacco and dark berries–for like a second. Then the classic traits of pinot come roaring through and it’s all rubies and roses and you’re wondering what just happened? This may come from the (I’m about to say terroir so just buckle up and relax, ok? It’ll only hurt for a minute) grape’s distinct terroir as it’s grown in Yountville in the Napa Valley, not in Sonoma where all the cool pinots are made. This is a difference of climate and soil and maybe proximity to the French Laundry that makes for a pinot that’s book smart and nerdish but really, in her heart, she wants to box.

Then we get into a 2016 Stoller, from the Willamette Valley in Oregon, made with natural yeast fermentation then aged in French oak barrels and here’s the thing. I can taste shortbread cookies and some kind of bright pink syrupy jam I don’t know the name of. It checks off all the standards of pinot but somehow adds a few more boxes for aspects that make no sense and don’t really belong in a wine review: [x] stately, [x] luxurious [x] voluptuous [x] flirtatious. Flirtatious? What does that even mean? Why would I write something so blatantly wine-writery like I’m aiming for some kind of badge?  I’ve used terroir and flirtatious within two paragraphs of each other. Who have I become?!

Look, I’m clearly no expert. I’m just like you, groping blindly through the vast warren of wine cellars in Chicago trying to figure out what’s good. But I can turn around in this subterranean journey and whisper to you, dear reader, who is also secretly trying to figure out good wine without anyone else knowing you don’t know diddly squat–this one, this one right here, this Oregonian pinot, this is good.

I ask Stratta about pairings on the new menu and halfway through her response I have to stop her because she’s clearly gone crazy. They serve a New York Strip with beets done several ways which are all gigantic flavors and look, it’s a New York Strip so let’s just order a titanic Cabernet and get this over with, right? But no, Stratta pairs it with a blended red (El Guidal Gigondas) not a cab–like Satan. Which is a delightful and unexpected education on what marries well with a seared steer. And she keeps going, talking about the wines she loves and making me want to move into their cellar: Domaine Chofflet-Valdenaire Givry 2015; a Hudson Old Masters 2012 merlot and cab franc; the 2014 Bonnie Doon “proper style” claret from California; the Bodegas Hermanos Ribera del Duero Crianza 2015; the R. Lopez de Heredia Viña Gravonia 2007 which is a full-bodied Spanish wine and I lose my place and I can’t keep up because she’s leaping across verticals and price points and flavor profiles like a dancer and I just want to give in and say take all my money. Bring me the wine.

We finish with a glass of champagne and that chocolate dessert I mentioned up top which almost got their pastry chef a Jean Banchet award and here’s the thing. When you’re in the Loop, when you’re banking and lawyering where LaSalle addresses turn into two digits and you want a glass of wine and swoonful dinner, you’re thinking of those places with wood paneling and blindingly alabaster linen and a wine list a mile and a half long and you’re terrified because you know you’re going to have to sell the house and maybe move in with your parents so you can pay the check. If you’re one of those people, skip the ostentatious oeuvre of big money steakhouses and sit down in the wood-paneled quietly elegant room at Steadfast with their face-meltingly delicious new menu. When it comes time to order the wine, ask for Daphne Stratta, shut up, and let her dance. You’ll be very, very glad you did.

Here's a taste of Steadfast's new menu and Stratta's recommendations:

  • Duck & Mushroom Tart: whipped goat cheese, apricot mustard, crispy duck, paired with the Sole e Olena Chianti Classico
  • NY Strip & Beets: beet puree, roasted beets, pickled beets, beet powder, roasted pearl onions, au poivre sauce, shaved beef jerky, paired with the E. Guigal Gigondas
  • Humboldt Fog Cheese Course: Humboldt fog cheese spread, roasted beets, candied pistachios, pistachio lavash, paire with Piper Heidsieck Champagne