Boss Shepherd’s, open since July 2014, is named in homage to Alexander “Boss” Shepherd. Shepherd was a powerful if controversial politician and one-time governor of the District of Columbia also known as the Father of Modern Washington. A fitting name for a restaurant very much a part of today’s modern Washington dining scene, far removed from the stuffy, stoic institutions more familiar to D.C.’s past.

Chef Jeremy Waybright brings a farm-to-table approach to Boss Shepherd’s, and he has developed a local, seasonal menu heavy on Southern comfort foods, some of which stay simple and classic, and others of which have been refined and tweaked to deliver something entirely new.

For the former, consider their 12-hour brined fried chicken. It showcases perfect flaky, crispy skin, adorned with a touch of sea salt providing a boost of extra flavor, and juicy, tender meat. It’s all served with a massive biscuit and several accompaniments. For the latter, consider their pot pie fritters, the soup dumplings of the fritter world, with luscious, liquidy chicken pot pie hidden inside a small, crispy fritter, served over a bed of thick sage and sausage gravy. One tried and true; one inventive and unique; and both are must-haves.

The menu also offers a raw bar, and plenty of seafood. Consider the fried local oysters, lightly coated in cornmeal and served with a vibrant caper mayonnaise, or a range of entrees such as their whole North Carolina trout, or their new country cioppino. The hearty stew incorporates massive gulf shrimp, hunks of catfish, clams, tasso and a spicy tomato broth, served over Carolina rice.

Another recommended choice is the bone marrow, a dish Waybright insisted upon including on the menu, featuring a split roasted beef femur bone. Well seasoned and prepared, it has just enough firmness and can be enjoyed on its own or spread thickly over grilled slices of bread. If you’re feeling bold, then be sure to ask about their whiskey luge. Get a paired whiskey poured down your emptied marrow bone for an unctuous, flavored little dram.

Yes, I did it.

Boss Shepherd's Bone Marrow Whiskey LugeSpeaking of whiskey, behind the bar you’ll find a well-focused list about 75 strong, with a range of unique bottles and private barrel selections, as well as a variety of flights available when you’re looking to explore several at once. Managing Partner Daniel Mahdavian, along with his staff, are happy to help you pair whiskey with your food, and have some excellent recommendations ready to go, offering a just-enough smoky Islay Scotch to match a briny oyster, for instance.

There’s also an extensive list of wines by the glass, as well as a locally dominated selection of beers, and well-honed cocktails. Check out the signature Boss Manhattan, made with Catoctin Creek Rye 92, Carpano, Fee Brothers Orange & Cherry bitters, a Luxardo maraschino cherry and an orange twist, or The Governor, made with Billy Wolf Pecan Bourbon, Fee Brothers Black Walnut & Cherry Bitters, and a Luxardo maraschino cherry. Other riffs on classics include the Wiseguy Sidecar, Green Hat Rickey, Chesapeake Old Fashioned using A. Smith Bowman single barrel whiskey, the Poll Watcher’s Sazerac, and the Boulevardier, with Few Whiskey, Campari, and Carpano.

Back to the food, bone marrow and fried oysters both also make an appearance in the restaurant’s new potato dumplings entree. Here, find simple, delicate potato dumplings in a rich, creamy bone marrow sauce, with fried oysters and strips of crispy ham providing counterpoints of weight and texture. The menu is always changing, and other new dishes include an oyster omelet, butternut squash soup, cast iron shrimp, and pork spare rib with hominy and maple-coffee braising liquid.

Their house hamburger, the Hamburg, comes highly touted. It’s made with a blend of ground chuck, short rib and brisket, and served on a brioche bun with cheddar and Maui sweet onions.

You won’t go wrong with an order of corn bread on the side, either. Really — there’s a lot you won’t go wrong with on the menu at Boss Shepherd’s.

If you still have room, the kitchen’s fine touch continues with their dessert selections. The chocolate espresso cake made with espresso fudge buttercream practically melts away in your mouth, and the sweet potato cheesecake, topped with toasted marshmallow fluff and served with candied pecans, is sure to please.

New Brunch

Boss Shepherd’s is launching a new live jazz brunch starting this Sunday, March 1, with the first 50 guests getting a free glass of Veuve Clicquot to celebrate the occasion. Every Sunday from 11am to 2pm, you’ll get your choice of starter, entree, and two brunch cocktails for $35.

Choose from starters such as the waffle egg & cheese, East Coast oysters, or steel cut oatmeal topped with brown sugar, crème fraiche and poached apples. Main course offerings include fried chicken & waffles, an oyster omelet with fried local oysters and a cauliflower puree in a hot sauce butter, egg benne with country ham, poached egg, frisee and smoked egg sauce atop grilled sourdough, and brioche French toast with candied pecans, bacon syrup and bourbon apples.

All prix fixe menu items will be available a la carte.


Boss Shepherd’s is located at 513 13th Street NW, right at the corner of 13th & E.