Preheat oven to 320°F.
Pat dry brisket. (wet brisket will not caramelize, it will just steam!) Season brisket with salt and pepper. Heat a braising pan or large Dutch oven, lightly coated with evoo over medium high heat.(if you don’t have a pan large enough to accommodate the whole piece of meat, cut the meat in half and sear each piece separately-do not be afraid to cut it in half)
Sear the brisket on both sides (about 5-7 minutes per side), being sure to allow each side to caramelize and turn dark brown. Remove brisket and set aside.
Add onions to the pan and caramelize being sure to season with salt and pepper, until dark brown and very soft, about 10-15 minutes.
Pour in the bottle of wine, then add 2 heads garlic, 2 cups chicken broth, and tomato paste.
Nestle brisket back into the pan. Add dates, cover and place in oven.
Braise brisket for 3 ½ - 4 hours or until a fork can be inserted easily without resistance.
Remove brisket and allow to cool before slicing across the grain.
Taste and adjust seasoning of the braising liquid, strain if desired, serve over brisket.