Set your cast iron dutch oven over medium-high heat to heat up! Or whatever heavy pot you are using.
Trim any large pieces of fat or silver skin from your meat, then cut into rough 2-inch, and season all over with 1 teaspoon of kosher salt and freshly ground pepper.
Add 1 tablespoon of the olive oil to your Dutch oven or other heavy-bottomed pot over medium until shimmering. Add half the beef and sear until the bottom is browned, 2 to 4 minutes. Flip the beef and sear until the second side is browned, 2 to 4 minutes more. Transfer to a plate. Add 1 tablespoon olive oil and the remaining beef to the pot and repeat browning.
Heat the remaining 1 tablespoon olive oil in the now-empty pot. Add the onion, carrot, and sauté until translucent and softened, 3 to 4 minutes. Add the garlic, Italian seasoning, and red pepper flakes. Cook, stirring often, until fragrant, about 1 minute.
Pour One can of tomatoes into a bowl and lightly crush with your hands and set aside.
In a food processor, process the other can of tomatoes to make tomato puree.
Add 2 tablespoons tomato paste and stir to coat the vegetables. Cook, stirring occasionally, until the tomato paste is darkened in color and some of it sticks to the bottom of the pot, 1 to 2 minutes. Pour in 1 cup dry red wine and scrape up any browned bits that have formed on the bottom of the pot with a wooden spoon. Simmer until the wine is reduced by about half, 1 to 2 minutes.
Add the beef, both tomatoes, anchovies, bay leaves, parmesan, and heavy cream.
If using fresh rosemary, wrap in cheesecloth and add.
Reduce the heat to low or place in a 325° oven Covered and simmer, stirring occasionally, until the meat is fork tender, 2 1/2 to 3 1/2 hours. Remove the pot from the heat. Remove and discard the bay leaf and rosemary. Use a potato masher to break the meat apart into shreds and break up any large pieces of tomatoes. (Alternatively, transfer the meat to a plate, shred it with two forks, and stir it back into the sauce.) Served tossed with pasta, gnocchi, or over creamy polenta.