2 tablespoons olive oil plus additional extra-virgin for drizzling
2.5 teaspoons sherry vinegar
4.5 lb tomatoes (9 medium)
Equipment
food processor
bowl
frying pan
ladle
knife
pot
sieve
blender
plastic wrap
cookie cutter
slotted spoon
cutting board
Directions
Cut a shallow X in the bottom of each tomato with a sharp paring knife and blanch tomatoes in 2 batches in a 5- to 6-quart pot of boiling water, 1 minute per batch.
Transfer tomatoes with a slotted spoon to a cutting board and, when cool enough to handle, peel, beginning from scored end, with knife.
While tomatoes are cooling, mince and mash garlic to a paste with a pinch of salt using a large heavy knife. Halve tomatoes crosswise, discard cores, and scoop seeds into a fine-mesh sieve set over a bowl. Press on seeds to extract liquid, then discard seeds. Coarsely chop tomatoes, then coarsely purée in batches with strained tomato liquid in a blender or food processor.
Heat 2 tablespoons oil in a deep 12-inch heavy skillet over moderately high heat until hot but not smoking, then sauté garlic paste, stirring, until golden, about 1 minute.
Remove skillet from heat and carefully add a small amount of puréed tomatoes near side of skillet (sauce will splatter and bubble vigorously). When bubbling subsides, add remaining purée, 1 3/4 teaspoons salt, and 1/2 teaspoon black pepper. Return skillet to heat and simmer, uncovered, stirring occasionally, 5 minutes. Cool sauce to room temperature, about 1 hour, then stir in vinegar.
Trim crusts from bread slices, reserving crusts for another use. If using Pullman loaf, cut 4 slices in half diagonally, then cut 1 round from 1 more slice using cookie cutter. If using round loaves, square off 5 slices of bread from center of loaf and cut triangles and 1 round in same manner. Ladle 3/4 cup sauce into soufflé dish and spread to cover bottom. Line bottom of dish with bread in a pinwheel shape, putting round in center and fanning triangles around it, covering sauce completely (you may have 1 triangle left over). Ladle 1 1/4 cups sauce over bread layer, spreading evenly to cover. Cover sauce with more bread slices, trimming as necessary to fit in 1 layer in dish. Repeat layering 3 more times, using 1 1/4 cups tomato sauce each time and ending with bread. Cover top layer of bread with remaining sauce. Cover surface with plastic wrap, then top with a plate small enough to just fit inside dish. Weight pudding with 2 heavy cans (about 2 pounds total) and chill at least 12 hours.
Remove weights and plate and run a thin knife around edge of dish. Invert a large plate over pudding and invert pudding onto plate. If any sauce remains in dish, spoon it over pudding.
Cut into wedges, drizzle with olive oil, and serve chilled or at room temperature.
• Tomato sauce can be cooled quickly in a metal bowl set in a larger bowl of ice and cold water, stirring occasionally. • Pudding can be chilled up to 24 hours.
