01 - Set oven temperature to 320°F.
02 - Pat brisket dry and evenly rub with olive oil, kosher salt, black pepper, smoked paprika, and brown sugar.
03 - Heat a large Dutch oven over medium-high heat and brown the brisket on all sides, approximately 3 to 4 minutes per side. Remove and set aside.
04 - Using the same pot, add onions, carrots, celery, and garlic and cook for 4 to 5 minutes until softened.
05 - Incorporate bay leaves and dried thyme, then pour in beef stock, crushed tomatoes, and red wine. Stir to combine.
06 - Place brisket back into the pot, nestle into the liquid, and bring to a gentle simmer.
07 - Cover the Dutch oven and transfer to the preheated oven. Cook for 3 hours, turning the brisket halfway through, until tender when pierced with a fork.
08 - Place sweet potatoes in a large saucepan, cover with cold water and add a pinch of salt. Bring to a boil, then simmer for 15 to 20 minutes until fork-tender.
09 - Drain sweet potatoes and return to the saucepan. Mash with butter, milk, salt, and pepper until smooth and creamy. Keep warm.
10 - Remove brisket from oven and let rest for 10 minutes. Skim fat from braising liquid and discard bay leaves. Slice brisket against the grain.
11 - Arrange sliced brisket over sweet potato mash and spoon the braising sauce and vegetables on top.