Oxtail Soup with Onions and Barley
['3 tablespoons vegetable oil, divided', '4 pounds oxtails or beef shanks', 'Kosher salt, freshly ground pepper', '3 large shallots, coarsely chopped', '2 medium carrots, peeled, coarsely chopped', '2 celery stalks, coarsely chopped', '4 garlic cloves, chopped', '2 cups dry red wine', '4 sprigs flat-leaf parsley', '2 sprigs thyme', '12 ounces small cipolline or pearl onions', 'Kosher salt', '3 tablespoons unsalted butter', '3 large red onions, thinly sliced', '1/3 cup bourbon', '2 cups low-sodium chicken broth', '1/2 cup pearl barley', 'Freshly ground black pepper', 'Prepared cornbread (for serving)']
Heat 1 tablespoon oil in a large heavy pot over medium-high heat. Season oxtails with salt and pepper. Working in 2 batches, cook until browned on all sides, adding 1 tablespoon oil between batches, 10-15 minutes per batch; transfer to a plate.
Add remaining 1 tablespoon oil to same pot. Add shallots, carrots, and celery. Cook, stirring occasionally, until golden brown, 8-10 minutes. Add garlic; cook, stirring, just until fragrant, about 1 minute. Add wine; cook, scraping up browned bits, until reduced by half, 5-8 minutes. Add parsley, thyme, and 4 cups water; return oxtails to pot. Bring to a boil, reduce heat, cover, and simmer, stirring occasionally, until meat is fork-tender, 3-3 1/2 hours.
Using a slotted spoon, transfer oxtails to a plate. Let cool slightly; shred meat, discarding bones. Strain stock through a fine-mesh sieve into a large bowl or measuring cup (discard solids). Skim fat from stock; add water if needed to measure 4 cups. DO AHEAD: Oxtail stock and meat can be made 2 days ahead. Let cool. Cover separately; chill. Rewarm before using.
Cook cipolline onions in a large saucepan of boiling salted water until tender, 5-8 minutes. Drain and let cool. Trim root ends; peel and set aside.
Heat butter in a large heavy pot over medium heat. Add red onions and cook, stirring occasionally, adding water by tablespoonfuls if pot becomes dry, until soft and deep brown, 45-60 minutes.
Remove from heat; add bourbon and reserved cipolline onions. Return to heat and cook, scraping up browned bits, until bourbon is evaporated, about 4 minutes. Add chicken broth, barley, and reserved oxtail stock. Bring to a boil, reduce heat, and simmer, stirring occasionally, until barley is tender, 45-60 minutes. Season with salt and pepper. DO AHEAD: Soup can be made 2 days ahead. Let cool slightly; chill until cold. Cover and keep chilled. Reheat before continuing.
Add reserved oxtail meat to soup. Thin soup with water, if needed. Divide soup among bowls and serve with cornbread alongside.
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