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1
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.
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2
Transfer tomatoes with a slotted spoon to a cutting board and, when cool enough to handle, peel, beginning from scored end, with knife.
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3
While tomatoes are cooling, mince and mash garlic to a paste with a pinch of salt using a large heavy knife.
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4
Halve tomatoes crosswise, discard cores, and scoop seeds into a fine-mesh sieve set over a bowl.
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5
Press on seeds to extract liquid, then discard seeds.
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6
Coarsely chop tomatoes, then coarsely puree in batches with strained tomato liquid in a blender or food processor.
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7
Heat 2 tablespoons oil in a deep 12-inch heavy skillet over moderately high heat until hot but not smoking, then saute garlic paste, stirring, until golden, about 1 minute.
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8
Remove skillet from heat and carefully add a small amount of pureed tomatoes near side of skillet (sauce will splatter and bubble vigorously).
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9
When bubbling subsides, add remaining puree, 1 3/4 teaspoons salt, and 1/2 teaspoon black pepper.
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10
Return skillet to heat and simmer, uncovered, stirring occasionally, 5 minutes.
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11
Cool sauce to room temperature, about 1 hour, then stir in vinegar.
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12
Trim crusts from bread slices, reserving crusts for another use.
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13
If using Pullman loaf, cut 4 slices in half diagonally, then cut 1 round from 1 more slice using cookie cutter.
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14
If using round loaves, square off 5 slices of bread from center of loaf and cut triangles and 1 round in same manner.
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15
Ladle 3/4 cup sauce into souffle dish and spread to cover bottom.
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16
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).
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17
Ladle 1 1/4 cups sauce over bread layer, spreading evenly to cover.
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18
Cover sauce with more bread slices, trimming as necessary to fit in 1 layer in dish.
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19
Repeat layering 3 more times, using 1 1/4 cups tomato sauce each time and ending with bread.
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20
Cover top layer of bread with remaining sauce.
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21
Cover surface with plastic wrap, then top with a plate small enough to just fit inside dish.
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22
Weight pudding with 2 heavy cans (about 2 pounds total) and chill at least 12 hours.
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23
Remove weights and plate and run a thin knife around edge of dish.
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24
Invert a large plate over pudding and invert pudding onto plate.
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25
If any sauce remains in dish, spoon it over pudding.
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26
Cut into wedges, drizzle with olive oil, and serve chilled or at room temperature.
