Season brisket all over with salt and pepper. Set a large stainless steel roasting pan over 2 burners set to medium-high heat, add oil, and heat until shimmering. Add brisket and brown on both sides, about 6 minutes per side. Transfer brisket to a work surface. Add onion, carrot, celery, and garlic to roasting pan and cook, stirring, until just starting to brown in spots, about 6 minutes; season with salt. Add wine and bring to a simmer while scraping up browned bits from bottom of pan.
Meanwhile, in a large cast iron or stainless steel skillet, heat oil over medium-high heat until shimmering. Add onion, carrot, celery, and garlic and cook, stirring, until starting to brown in spots, about 6 minutes; season with salt. Add wine to vegetables and bring to a simmer, then stir in ketchup and tomatoes. Scrape vegetables into roasting pan with brisket.Add thyme and bay leaves to roasting pan and cover well with foil.
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