The Diplomat

Owned and operated by 2022 James Beard winner for Best Chef Midwest, Dane Baldwin, The Diplomat serves modern American food in a tapas/family style. Although the plates are served with sharing in mind, almost all of them, that we have tried, have been substantial enough to stand on their own. To be fully transparent from the start, we adore this restaurant and even joke that we have a line in our budget dubbed “Diplomat” for our frequent trips.

Environment

When entering the restaurant you find yourself in a bar area nearly completely separate from the dining room and the first time entering can definitely be a little confusing. The bartenders are quick to guide you to the area where the wait staff are ready to check you in and get you to your seats to get your dining experience going. Once seated, it’s hard to not take in the rather interesting décor around, something of a cross between a home library and a Harry Potter movie. I know that sounds a little bizarre, but after dining there you definitely kinda “get it”.

After being sat, a simple menu is given that contains one page of food, a page of wine and a page of drinks. Like many of the other “farm-ish to table-ish” restaurants, the menu has consistently undergone slight changes each time we’ve been, so what you see online is often not exactly what you get there. I am not saying you look at the menu online and go in and it’s completely different. Just that the menu may have 1-4 items swapped out for something more seasonal or, I’m speculating here, something the head chef thought looked/sounded good for that night.

Drinks

An cocktail list that is mostly plays on traditional drinks, the majority of which are focused on more flavorful liquors compared to just alcohol content. We have tried several different cocktails at our trips here and they are all good compliments to the style of food. For the most part, the drinks here definitely skew to the "stronger" side, but we never find that the flavor of the cocktail is enveloped by just liquor taste. This time we tried the Still Crazy, Aperol These Years (Jungle Bird).

Still Crazy, Aperol These Years (Jungle Bird) is a gin based drink with aperol, pineapple, lime, and Luxardo cherry syrup and it’s a nice addition to the menu since the menu tends to favor darker liquors. It’s refreshing and fruity, having a nice balance of being sweet without going over the top. I would definitely order this again.

Food

Although not explicitly marked, the menu presents with a traditional American restaurant style, with starters, mains, and desserts but with wiggle room between what constitutes a starter vs. a main. The left side of the menu mostly falls under the starter category, while the right side contains the the more hearty foods with a small dessert section at the bottom. But, again, we have played around with the ordering on what constitutes a starter and main, plus the staff are always willing to help parse out service in a way that they find makes the most sense for the customer.

Starters

Of the items that fall as a more traditional “starter”, we ended up treating these like a true small plate restaurant. We chose the Octopus and the Whey Risotto, and shared those between us.

A common theme throughout many dishes at The Diplomat is a playfulness alongside inventiveness. The Octopus is served with fregola, calabrian chili aioli, citrus segments and a marinated olive salad. At face value the components do not scream playful, but upon arrival you get a dish that, at least to me, was far different than expected. The Fregola and calabrian chilis are mixed together and presented in a round as the highlight at the center of the plate, which is then flanked by the marinated olives and citrus slices. These items create a form of a deconstructed pasta salad that is paired with some beautifully prepared octopus. Although the dish is named after the protein, the sides of this dish really make the entire plate sing. Essentially XL sized couscous, the fregola helps provide a nice counter-texture to the plate, and the calabrian chili aioli really helps bring a slight kick to everything. The olive salad has its claim to being the most important part of the plate. It introduces a brightness to everything, with its bite and tang, that truly helps bring it all together. While the olives provide a tangy brightness, the citrus manages to provide a sweet brightness. Each component is great on their own, but this really is a dish that is greater than the sum of its parts. I believe a singular complete bite of this can compete with almost any dish out there.

I (Olivia) was skeptical about this dish originally, but the server said it's one of her favorites and we wanted one more dish to order. I’ve been trying to go out of my comfort zone so we decided to order the Whey risotto. When I tell you that I frequently think about this dish and wonder when I can go back and get more I am not lying. The shredded leeks and celery root along with crunchy pistachios break up the creamy risotto texture and the candied fennel seed is subtle enough to be there without overpowering the dish. It’s a big, warm hug in a bowl and I want to eat it forever and ever. If you’re on the fence do yourself a favor and just get the risotto.

Main

You know that meme that’s like “this is what the ideal male body type looks like”? Well, the Chicken Leg Confit dish is what the ideal piece of chicken looks like. When I say ideal chicken, I mean it is a fall off the bone while still managing to provide a toothsomeness, paired with perfectly rendered skin. That crispy chicken skin is a work of art. The fat has been fully rendered down to where no bite of the skin has any gelatinous parts at all, and the entire leg piece is perfectly browned. The sides of this dish have always differed from what is on the posted menu. In our experience, it has mostly been served with gnocchi and veggies. The play on this gnocchi is that it is served with a garlicky, buttery sauce that contains little bits of ham.

I will concede that this take may upset some burger truthers out there, but this burger is in contention for the best burger in MKE. Exactly as it sounds, a play on a McDonald’s Big Mac, The Diplomac is everything you want from a burger and then some.

3 pieces of bun, 2 beef patties, tomato, lettuce, American cheese, “1000 island” dressing (aka big mac secret sauce), pickles and onion. Even with all that going on, your first bite is truly highlighted by the taste of high quality beef that is cooked to perfection. Then you get the gooey melty cheese, dressing, and everything else combined into one umami bomb of a bite. By the time you look up you realize that you’ve already eaten your half of the burger before your dining partner has taken one bite. I can understand some people that may be slightly underwhelmed by the dish, but at the same time there is only so much you can do to upscale a burger without it losing its identity and I find that this dish toes that line very well.

Desserts

While there’s not tons of desserts listed in The Diplomat’s dessert section, there is a curated variety to choose from, usually also including a newer seasonal option, and everyone will be able to find something to enjoy.

The Peanut Butter Pie is silky smooth, with the filling sandwiched between an Italian buttercream frosting and a crunchy graham cracker crust. The filling is pretty standard in flavor to what you would traditionally think of when eating any other peanut butter pie, but the mix of the salty buttercream with the crunchy crust brings it all together. Truthfully, the caramelized bananas on top weren’t my favorite since they were pretty bitter, but that wouldn’t stop me from ordering this dessert again. If you like peanut butter, you will love this pie.

Similar to the rest of the menu, even the desserts sometimes receive a touch of seasonal changes. Listed as being paired with a strawberry compote, when I got the Sour Cream Cheesecake it was served with grapefruit supreme's instead. Which, if you read our Il Cervo review, you know that I'm a sucker for citrus in desserts so this was a win for me. This dessert served as somewhat of a pallet cleanser to the much heartier meal and really helped end the night on a high note.

Final Thoughts and Recommendation

We said it at the start and we’ll reiterate it here. We adore The Diplomat. High level cuisine served without the feeling of needing to be wearing your Sunday best is just about where we would say our food “lane” is. And that is exactly what a night here exemplifies. We strongly recommend making sure you find a night to explore this Brady Street establishment.

TL;DR

Environment: 9.5

Drinks: 8.7

Starters: 10

Mains: 9.6

Dessert:8.4

Price: ~$140+

Overall: 9.6

Drinks: Still Crazy, Aperol These Years & Others

Starters: Octopus & Whey Risotto

Mains: Chicken Leg Confit & The Diplomac

Desserts: Peanut Butter Pie & Sour Cream Cheesecake