Preheat oven to 300°F, and preheat a large braising pan or nonstick skillet over high heat.
Season the brisket with 1/8 cup olive oil, salt, pepper and paprika, rubbing the spices into the meat.
Place the brisket fat cap side down into the preheated skillet and brown for at least 5 minutes on each side until all sides have a deep brown crust.
Remove the brisket from the pan and set aside.
Add the remaining olive oil and the onions to the drippings in the pan.
Sauté about 6 minutes, until onions are soft and beginning to caramelize.
Add the garlic and tomato paste and stir until tomato paste caramelizes, about 1 minute.
Add the red wine and red wine vinegar and stir to incorporate.
Add crushed tomatoes, brown sugar, chopped dates, bay leaf, carrots and celery, and stir until the vegetables are coated.
Add the seared brisket back into the pan and add beef broth.
Cover the pan with foil and bake for 6 to 7 hours until the meat is tender and flaky.
Once out of the oven, carefully remove the brisket from the pan and allow to rest for about 30 minutes before slicing.
Prepare cauliflower mash.
Fill a medium-sized stock pot with 4 cups water, followed by a pinch of salt.
Bring water to a boil, add cauliflower and reduce heat to medium-low.
Simmer the cauliflower until fork-tender, about 15 minutes.
Carefully remove cauliflower from the pot, reserving some of the cooking liquid.
Place cauliflower directly into a food processor bowl fitted with a chopping blade.
Pulse the florets until smooth, adding the reserved liquid until desired consistency is reached.
Add olive oil, chopped herbs, a squeeze of lemon and salt and pepper to taste.
Serve brisket with herbed cauliflower puree and roasted vegetables.