Preheat oven to 325 degrees.
Season brisket liberally on both sides with kosher salt and freshly-ground black pepper.
Heat a large skillet(that can be placed in oven)or Dutch oven with a lid over medium-high heat on stove top. Add olive oil to coat the bottom of the pan. Sear both sides of brisket fat-side down first, until golden brown. Remove to a sheet pan.
Add garlic cloves and onion rings to the remaining oil in the pan. Cook and stir until garlic begins to turn golden and sweet onions are limp and lightly colored.
Add red wine and deglaze the pan by scraping up the browned bits from the bottom of the pan. Add beef stock, tomato paste, bay leaves, basil and oregano. Bring back to a simmer, then turn off heat. Move garlic and onions to the side and return brisket to the skillet. Spoon garlic and onions over the top of the brisket, cover tightly, and place in the oven.
Bake for 1 hour at 325 degrees F. Reduce heat to 300 degrees and bake an additional 1 1/2 to 2 hours, or until brisket is fork-tender. Remove brisket to a platter and cover with foil to rest for 10 minutes.
Remove half of of garlic cloves and most of onions to a bowl. Skim off excess oil from the pan gravy and discard. Blend pan gravy and remaining garlic until smooth in a food processor. You can add a little cornstarch slurry(cornstarch whisked with a little water) to thicken gravy, by bringing it back to the stove and returning to a boil. Return reserved whole garlic cloves and onions to the gravy.
Slice brisket diagonally across the grain. Serve with pan gravy. Enjoy!