Pappa al Pomodoro reminds me of September in Tuscany, when the tomato season is finishing up and the tomatoes are very ripe. A terrific way to use stale bread, the only real expense here is for the olive oil—you should use the very best you have; it truly makes a difference.
In the winter, we serve the pappa very hot with the season’s first-pressed olive oil, olio nuovo. In the summer we like it at room temperature, so you can let it sit for a little while before serving. If it gets too thick on standing, thin with a little stock or water just before the final drizzle of olive oil.
Start by pureeing the tomatoes. Place a food mill over a large bowl and pour in the tomatoes.
Grind the tomatoes, letting the puree fall into the bowl.
Set the pureed tomatoes aside. Cut the bread into medium-to-large chunks with a serrated knife.
Warm the olive oil in a Dutch oven or large saucepan over a high flame. When hot, add the bread chunks and cook, stirring continuously with a wooden spoon, until they begin to brown.
Add more oil, if needed, to help the cubes brown and get crispy. Add the garlic, sage, and basil (if using) and continue stirring until the bread is golden brown. With the flame still high, add the stock.
Expect a lot of noise and steam when the stock hits the bottom of the pan, then the stock will reduce rapidly. Lower the flame, season with salt and pepper, and add the pureed tomatoes and some water, enough to quickly rinse the bowl the tomatoes were in. Use the wooden spoon to stir gently to incorporate the bread into the tomatoes and break down the larger chunks.
Cook for about 20 minutes, stirring now and then, until the water from the tomatoes has reduced and been absorbed by the bread. The pappa should be soft and not dry, and well incorporated, almost like a porridge.
If there are any large pieces of bread, break them up with your spoon. Fish out and discard the whole garlic cloves. Turn off the heat, taste, and adjust the seasoning. Serve with a drizzle of your very best olive oil.