Short Rib Grilled Cheese Recipe

Preheat and season

Preheat oven to 325°F (160°C). Pat short ribs dry with paper towels. Season all sides with 1.5 tsp kosher salt and 1 tsp freshly ground black pepper.

Sear

In a large heavy oven-safe Dutch oven or deep skillet, heat 1 tbs vegetable oil over medium-high heat until shimmering. Sear short ribs in batches, 2–3 minutes per side, until deeply browned. Transfer seared ribs to a plate and set aside.

Build braising base

Reduce heat to medium. Add the chopped onion, carrot, and celery to the pot and cook, stirring, until softened, about 5–7 minutes. Add the smashed garlic cloves and 2 tbs tomato paste and cook 1–2 minutes, stirring, until the paste darkens slightly.

Deglaze and braise

Pour in 1 cup dry red wine to deglaze, scraping up browned bits with a wooden spoon. Simmer until the wine is reduced by about half, 3–5 minutes. Add 2 cups beef stock, return the short ribs to the pot, add thyme sprigs and 1 bay leaf. The liquid should come halfway up the ribs; add a touch more stock or water if needed.

Oven braise

Bring to a gentle simmer on the stovetop, then cover and transfer to the oven. Braise until meat is very tender and falling from the bone, 2.5–3 hours. Check once at about 2 hours and add a splash of stock if liquid is too low.

Shred and reduce sauce

Remove the pot from the oven. Transfer short ribs to a tray and let cool slightly. Strain the braising liquid into a saucepan, pressing solids to extract flavor, and discard solids and herb stems. Shred the short rib meat with two forks, discarding excess fat and bone. Simmer the strained braising liquid over medium-high heat until reduced to about 1/2–3/4 cup and thickened (5–10 minutes). Toss shredded short rib meat with 2–3 tbs of the reduced sauce to keep moist. Taste and adjust seasoning with salt and pepper.

While the short ribs braise (or in the last hour), heat 1 tbs unsalted butter and 1 tsp olive oil in a wide skillet over medium-low heat. Add 2 cups thinly sliced yellow onions and 1/2 tsp kosher salt. Cook slowly, stirring every few minutes, until onions are deep golden brown and softened, 25–35 minutes. If onions begin to stick or brown too quickly, lower the heat and add a splash (1–2 tbs) of water.

About 5 minutes before the onions are done, sprinkle 1/2 tsp granulated sugar over them and stir to help caramelization. Finish with 1 tsp balsamic vinegar, cook 1 minute, then remove from heat. Taste and adjust salt if necessary.

Prepare spreads (optional)

If using, mix 2 tsp mayonnaise with 1 tsp horseradish. Spread a thin layer on the inside of two slices of bread per sandwich for a bright counterpoint to the rich short rib.

Assemble sandwiches

Butter the outside of each bread slice with softened butter (about 3/4 tbs per slice). On the unbuttered side of the bottom slice, layer 1/4–1/3 cup shredded short rib (per sandwich), then 2–3 tbs caramelized onions, and top with about 1/2 cup (packed) grated sharp cheddar. Top with the second slice of bread, buttered side out.

Grill

Heat a heavy skillet or griddle over medium-low to medium heat. Place sandwiches in the skillet and cook gently, pressing lightly with a spatula or a sandwich press, until the bread is deep golden brown and the cheese begins to melt, about 3–4 minutes per side. If the bread is browning too quickly before the cheese melts, lower the heat and cover the pan with a lid for 1–2 minutes to trap heat and finish melting the cheese.

Finish and rest

Transfer sandwiches to a cutting board and let rest 1–2 minutes, then slice in half. Serve immediately so the cheese is gooey and the short rib remains warm.