Preheat oven to 325°.

Drizzle brisket with olive oil, then season with salt and pepper.

Place a large Dutch oven or heavy-based pot over medium-high heat and add ¼ cup of olive oil. Place the brisket in the pot and sear it on both sides until golden brown.

Remove from the pot and set aside.

Add to the pan, carrots, onions, celery and brown the vegetables. Then add the garlic, tomatoes, red wine, bay leaf, thyme, rosemary, parsley.

Place the brisket back in the pot, cover and roast in the oven for 3 hours until tender. Remove the brisket, place on a cutting board and let it rest for 15-20 minutes. Strain out the vegetables and pour off the excess fat. Pour over the brisket.

In a large sauté pan, heat the oil on high heat until it starts to smoke. Carefully add the heirloom tomatoes. Toss them around for a few seconds until the skin starts to burn. Then, remove from the pan.

Set the heat to medium. Add the onions and squash and cook for 5 minutes. Add the tomatoes back to the pan and set them aside.

Slice the brisket across the grain and serve with the vegetables. Garnish the brisket with fresh rosemary.