The best part about sweet and sour brisket is that everyone (and their grandmother) has their own method for achieving the same flavor. Some people swear by dates and vinegar, while others turn to a combination of Welch’s grape jelly and powdered onion soup mix; my family's secret to brisket success is the browned bits, which comes from searing the brisket and caramelizing the onions. No matter which way you make it, all of that scraping, searing, and hours-long simmering results in the same iconic flavor: It's like a less acidic Carolina BBQ—but Jewish. It may not be the prettiest dish, but a plate of this pure-comfort brisket is perfect during the holidays no matter what you’re celebrating. —Cara Nicoletti
Preheat oven to 300° F. Place the dried prunes, orange juice, garlic, apple cider vinegar, and brown sugar in a blender and process until smooth.
Pat the brisket dry and season it liberally with salt and pepper on both sides. Heat 3 tablespoons olive oil in a wide, heavy-bottomed Dutch oven. Sear the brisket until a nice crust appears, about 4 minutes per side.
Set brisket aside and heat remaining 3 tablespoons of oil in the Dutch oven, scraping up the brown bits from the bottom of the pan while the oil heats. Add butter, sliced onions, and shallots, and season with salt and pepper. Cook over medium heat until the onions and shallots are golden brown, about 20 minutes.
Transfer the shallots to a bowl and add the chicken stock to the onions, bringing it to a boil and scraping up the brown bits that have formed on the bottom of the pan. Return the brisket to the pot, fat-side up, and pour in the orange juice mixture, along with the crushed tomatoes. Bring the mixture to a boil over medium heat and stir sauce to unify.
Cover the Dutch oven, transfer it to the oven, and cook for 2 hours. After 2 hours, add the shallots, carrots, and potatoes. Cover and cook for 1 hour.
After 1 hour, uncover the Dutch oven and return to the oven to cook for 1 more hour, spooning sauce over brisket occasionally to keep it moist.
Remove from the oven and let the brisket rest in the Dutch oven for 30 minutes before transferring to a cutting board and slicing against the grain into thin strips. Season the sauce with salt to taste and serve, layering slices of brisket with sauce, and surrounding them with potatoes carrots and shallots.
Cara Nicoletti is a butcher and writer living in Brooklyn, New York. Cara started working in restaurants when she moved to New York in 2004, and was a baker and pastry chef for several years before following in her grandfather and great-grandfathers' footsteps and becoming a butcher. She is the writer behind the literary recipe blog, Yummy-Books.com, and author of Voracious, which will be published by Little, Brown in 2015. She is currently a whole-animal butcher and sausage-making teacher at The Meat Hook in Williamsburg.