Pat the brisket dry with a paper towel and season liberally with salt and pepper.
Heat the oil in a large dutch oven and add the brisket to the pot. Sear until deeply browned, approximately 5-8 minutes. Flip and brown on the opposite side.
Remove the brisket from the pot and transfer to a platter.
Add the onions to the pot and cook until slightly softened, approximately 2-3 minutes.
Stir in the garlic and cook for 1 minute.
Add the tomato paste and stir to combine. Cook for 1-2 minutes longer.
Return the brisket to the pot and top with the onions.
Add the red wine, tomatoes, beef stock, brown sugar, Italian seasoning, garlic powder, onion powder and paprika. Stir to combine. Be sure the brisket is submerged under the onions and liquid.
Cover the brisket with a lid and transfer to the oven.
Cook the brisket for 1 1/2 -2 hours or until fork tender.
Remove the brisket from the oven, uncover and transfer the brisket to a large cutting board. Rest the brisket for 10-15 minutes.
Slice and serve with the onions and braising liquid.