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1
Preheat oven to 375u00b0 F.
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2
Halve or quarter tomatoes, depending on size, and scrape out the seeds (no need to be meticulous.) Lay cut side down in a baking dish along with the onion and garlic cloves. Scatter the oregano branches around, drizzle everything with the olive oil, and sprinkle with the kosher salt and pepper. Roast for about 45 minutes, basting once or twice with the liquid in the pan, until the tomatoes begin to caramelize and the garlic cloves are soft.
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3
Remove from the oven and cool for few minutes, then pull off the tomato skins (not completely necessary, but it's a cinch to do and makes the soup's texture a little nicer). Discard the oregano branches. Squeeze the garlic from its skin onto the baking sheet, holding back 2 cloves to use in the mayonnaise mixture.
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4
Transfer the roast vegetables and all the accumulated pan juices to a large pot and add the chicken broth, sugar, the red pepper flakes, vinegar, and chopped basil. Bring to a simmer, for around 10 minutes.
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5
Use an emulsion blender to puree the soup until it's fairly smooth. Taste for seasoning, and add more salt if necessary.
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6
Meanwhile, make the roasted garlic mayonnaise. Mash the 2 remaining roasted garlic cloves to a paste. Whisk them into the mayonnaise. If the mixture is too thick to drizzle, whisk in a little water (go easy, it only takes a little).
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7
Pan-fry the diced bacon until crispy and drain well on a paper towel-lined plate.
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8
To make the croutons, drizzle the day-old bread with a little olive oil, sprinkle with a pinch of kosher salt, and toss to coat lightly. Spread in a single layer on a baking sheet and toast in a 375u00b0 F oven (while the vegetables roast, if you're a multi-tasking sort) for about 10 minutes or until golden brown, turning once or twice. Set aside.
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9
Toss arugula (or lettuce) leaves with a drop of olive oil-just enough to add a hint of shine.
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10
Serve the soup chilled, room temperature, or hot, topped with a drizzle of the garlic mayonnaise, a small mound of arugula, and a scattering of croutons and bacon bits.
