Tomato-Bread Pudding

12 ripe medium tomatoes
(about 3¹/₂ pounds)
3 cloves garlic, minced
Kosher salt and freshly
ground black pepper,
to taste
¹/₄ cup plus 2 tablespoons
extra-virgin olive oil, plus
additional for greasing
the dish
1 large baguette, sliced on the
bias about ³/₄ inch thick
5 tablespoons minced flatleaf
parsley
5 tablespoons finely chopped
basil

Bring a pot of water to a boil. Core the tomatoes, and blanch in the boiling water for about 30 seconds to loosen the skins. Transfer the tomatoes to a strainer. When cool enough to handle, peel off the skins. Cut the tomatoes in half horizontally and position the strainer over a medium bowl; scoop the seeds and pulp from the tomatoes into the strainer. Press the pulp to extract as much of the juice as possible.

Arrange the tomato halves, cut side up, on a large plate. Sprinkle with the garlic and season moderately with salt and pepper. Drizzle with two tablespoons of the olive oil and allow to sit for 30 minutes. Pour any accumulated juice into the strained tomato juice.

Preheat a cast-iron grill pan or preheat the broiler. Brush the baguette slices on both sides with the remaining one-quarter cup of olive and grill or broil until toasted, one to two minutes per side. Season the toasts with salt and pepper and transfer to a large plate. Grill or broil the tomatoes on one side until lightly charred, about three minutes, then return to the plate.

Preheat the oven to 350 degrees. Lightly oil a shallow 3-by-9-inch baking dish. Arrange half the tomatoes on the bottom, pressing them down with a spatula. Sprinkle the tomatoes with two tablespoons each of the parsley and basil; season generously with salt and pepper. Top the tomatoes with half the toasted baguette slices. Repeat the procedure with the remaining tomatoes, two tablespoons each of the parsley and basil, and the remaining toast. Pour about one cup of the juice evenly over the bread pudding. Place a piece of aluminum foil over the pudding, weight it down with another pan.

Place the dish in the oven and bake until the liquid is absorbed and the tomatoes are very soft, about 30 minutes. Remove the weight and foil and bake until the top of the pudding is crisp, about 10 minutes more. Allow to stand for 15 minutes, sprinkle with the remaining one tablespoon each of parsley and basil, and serve.

Makes six servings.