Ingredients

• 2 tablespoons finely chopped garlic
• 1/4 cup finely chopped shallot
• 2 tablespoons finely chopped thyme
• 1 1/2 teaspoons finely chopped rosemary
• 1 tablespoon extra-virgin olive oil
• 2 tablespoons kosher salt
• 1 (4- to 4 1/2-pound) trimmed beef tenderloin roast, tied
• 8 large garlic cloves
• 1/3 cup extra-virgin olive oil
• 4 (14-ounce) cans diced tomatoes, drained
• 1/2 teaspoon finely chopped thyme
• 1/2 teaspoon finely chopped rosemary
• 1/2 California or 1 Turkish bay leaf
• 1/4 teaspoon sugar
• 1 cup Madeira (preferably Verdelho), divided
• 1/4 cup water

Instructions

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.
2. Let stand at room temperature 1 hour before roasting.
3. Make confit: 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. Mash garlic into tomatoes with spatula, then stir in 1/4 cup Madeira. Discard bay leaf.
4. 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.
5. Mash garlic into tomatoes with spatula, then stir in 1/4 cup Madeira. Discard bay leaf.
6. Roast beef: Preheat oven to 350°F with rack in middle. 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 120°F, 35 to 45 minutes. Transfer to a cutting board and let stand, loosely covered with foil, 15 to 20 minutes (temperature of meat will rise to about 130°F, for medium-rare). 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. Cut off and discard string from beef, then cut meat into 1/2-inch-thick slices. Serve with confit.
7. Preheat oven to 350°F with rack in middle.
8. 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 120°F, 35 to 45 minutes.
9. Transfer to a cutting board and let stand, loosely covered with foil, 15 to 20 minutes (temperature of meat will rise to about 130°F, for medium-rare).
10. 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.
11. Cut off and discard string from beef, then cut meat into 1/2-inch-thick slices. Serve with confit.