5lbs of tomatoes, halved the long way and stems cut out
2 heads of garlic, root end chopped off for roasting (see here)
2 tablespoons olive oil + more for drizzling
2 small carrots, diced
1 medium onion, diced
2 stalks of celery, diced
1 bay leaf
1 cup cup red wine
2 tablespoons fresh oregano leaves, chopped
1/4 fresh basil leaves, chopped
1/2 to 1 teaspoon crushed red pepper flakes
Kosher salt and cracked black pepper

Preheat the oven to 275 degrees F. Line a baking sheet with parchment paper.

Wrap each head of garlic in tin foil, making sure to drizzle them with a healthy amount of olive oil and salt and pepper. Make sure the cut side remains up during the roasting process. In a bowl, toss the tomatoes with 1 tablespoon olive oil, salt, and pepper. Place halved tomatoes, skin side up, on a rimmed baking sheet. Bake in the oven for 1 hour, or until the tomatoes have “slumped” and are releasing their juices. Repeat this process until all tomatoes have been roasted. Set tomatoes aside and allow to cool. Once tomatoes are cool enough to handle, remove their skins and reserve the juices. Remove the garlic heads and carefully squeeze them to release the garlic “paste” from each clove. Reserve roasted garlic with the tomatoes and their juices.

In a dutch oven or large pot, 2 tablespoons  olive oil over medium heat. Add in onion, celery, and carrot, and cook until the vegetables are tender, about 10 minutes. Deglaze the pan with red wine, and add in the bay leaf, basil and oregano. Allow to simmer for a few minutes, and then add in the roasted tomatoes and garlic, and salt & pepper. Allow to simmer uncovered over low heat for 30 to 60 minutes, stirring occasionally. Cover the pot and simmer for another 60 minutes, stirring occasionally (the longer you let this sauce simmer, the better it will be). Remove the sauce from heat. After 30 minutes, taste and adjust seasonings as desired. Blend with an immersion blender (or food processor) until smooth.

Store sauce in an airtight container and refrigerate or freeze.