Cry Me A Beef Recipe

Prep and season

Pat beef cubes dry with paper towel. Season with kosher salt and black pepper, then toss with the all-purpose flour until lightly coated; shake off excess flour.

Brown the beef

Heat vegetable oil in a heavy-bottomed Dutch oven or skillet over medium-high heat until shimmering. In batches (do not crowd), brown the beef cubes 2–3 minutes per side until a deep golden crust forms. Transfer browned beef to a plate and set aside.

Sauté aromatics

Reduce heat to medium. Add the chopped onion, carrot and celery to the pot and cook, stirring, until softened and starting to brown, about 6–8 minutes. Add the minced garlic and cook 30–45 seconds until fragrant. Stir in the tomato paste and cook 1–2 minutes to caramelize.

Deglaze and simmer

Pour in the red wine (or extra stock) to deglaze the pan, scraping up browned bits. Add the beef stock, soy sauce, Worcestershire sauce, bay leaf, thyme and brown sugar. Return the browned beef and any accumulated juices to the pot. Bring to a gentle simmer, then cover and reduce heat to low. Simmer gently for 1.5–2 hours, or until beef is very tender and shreddable. Check at 1 hour and add a splash of stock if liquid gets too low.

Shred and reduce

Remove bay leaf and thyme sprig (if used). Use two forks to shred the beef in the sauce to your desired consistency. If the braising liquid is thin, increase heat to medium-high and reduce uncovered for 8–12 minutes until thickened to a saucy consistency. Taste and adjust seasoning with salt, pepper or a touch more brown sugar or soy to balance.

Heat butter and olive oil in a medium skillet over medium-low heat. Add the thinly sliced red onions and a pinch of salt. Cook slowly, stirring occasionally, until the onions are soft and deeply golden, about 20–25 minutes. Stir in the brown sugar and continue to cook 2–3 minutes to caramelize further. Add the balsamic vinegar and red wine vinegar, stir and cook 1–2 minutes until jammy. Season with salt and black pepper to taste. Remove from heat and keep warm.

Toast rolls: Heat a skillet over medium heat. Spread butter on cut sides of the ciabatta rolls and toast, buttered-side down, until golden and crisp, about 1–2 minutes. Remove from heat.

Prepare spread: If using horseradish aioli, taste and adjust for heat. Spread about 1 tablespoon of aioli on each bottom roll half.

Build sandwiches: Pile 4–5 ounces (about 1/2 cup) of shredded braised beef onto each bottom roll. Spoon 2 tablespoons of onion jam over the beef. Top with a slice of provolone or Swiss cheese. If you like heat or acidity, add pickled jalapeños or pickles to taste (about 1–2 tablespoons).

Melt cheese: Place assembled open sandwiches under a broiler for 1–2 minutes or return to the skillet and cover briefly until cheese melts. Watch closely to avoid burning.

Finish and serve: Place top roll on sandwich, garnish with chopped parsley, and serve immediately with extra braising sauce on the side for dipping.