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1
Stir together garlic, shallot, herbs, oil, kosher salt, and 2 teaspoons pepper, then rub all over beef. Marinate in a sealed large bag, chilled, 1 day.
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2
Let stand at room temperature 1 hour before roasting.
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3
Cook garlic in oil in a large heavy skillet over medium-low heat, turning occasionally, until golden, 10 to 15 minutes. Add tomatoes, thyme, rosemary, bay leaf, sugar, 1/4 teaspoon table salt, 1/8 teaspoon pepper, and 1/2 cup Madeira and briskly simmer, stirring frequently and crushing tomatoes with a heatproof rubber spatula, until tomatoes start to break down and oil separates slightly, about 1 hour.
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4
Mash garlic into tomatoes with spatula, then stir in 1/4 cup Madeira. Discard bay leaf.
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5
Preheat oven to 350u00b0F with rack in middle.
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6
Roast beef in a 17- by 11-inch shallow heavy baking pan until an instant-read thermometer inserted into center of thickest part of meat registers 120u00b0F, 35 to 45 minutes.
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7
Transfer to a cutting board and let stand, loosely covered with foil, 15 to 20 minutes (temperature of meat will rise to about 130u00b0F, for medium-rare).
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8
Meanwhile, add water and remaining 1/4 cup Madeira to baking pan and deglaze over medium-low heat, stirring and scraping up brown bits, 1 minute. Stir into tomato confit.
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9
Cut off and discard string from beef, then cut meat into 1/2-inch-thick slices. Serve with confit.
