Bring meat to room temp. Pat dry, season with pepper. Heat olive oil in large oven-proof pot or Dutch oven and sear meat on all sides. Remove meat from the pot and set aside.
3.
Add more oil if necessary and sauté onions until translucent. Add ½ cup wine, and scape up browned bits on the bottom of the pot.
4.
In a small bowl, mix remaining ½ cup wine, ketchup, and molasses or brown sugar. Add ketchup mixture to pot along with brisket.
5.
Cover pot with lid or use heavy duty aluminum foil to cover tightly. Roast for 2 hours. Remove pot from the oven, flip brisket, and baste with cooking liquid. Cover pot and return to oven to roast for 1 hour more.
6.
Remove from the oven. Let cool, then refrigerate at least 8 hours or overnight.
7.
To serve, slice brisket and arrange in serving dish. Cover with remaining gravy. Reheat at 300 degrees F for 30 minutes before serving.
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