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Between slices of golden brown sourdough bread, layers of crispy smoked bacon and melty monterey jack find sweet and tangy complement from fresh tomatoes cooked with garlic and sherry vinegar until soft and jammy.
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Preheat the oven to 450°F. Wash and dry the fresh produce. Cut off and discard the bottom 1/2 inch of the broccoli stem; cut the broccoli into small florets. Halve the tomatoes. Peel and roughly chop 2 cloves of garlic. Grate the monterey jack on the large side of a box grater.
Line a sheet pan with foil. Arrange the bacon on the foil in an even layer. Roast 8 to 10 minutes, or until cooked through and crispy. Transfer to a paper towel-lined plate.
Meanwhile, place the broccoli florets on a separate sheet pan. Drizzle with olive oil and season with salt and pepper; toss to coat. Arrange in an even layer. Roast 14 to 16 minutes, or until browned and tender when pierced with a fork. Remove from the oven. Top with half the vinegar; carefully stir to coat.
In a medium pan (nonstick, if you have one), heat a drizzle of olive oil on medium-high until hot. Add the halved tomatoes in an even layer. Cook, without stirring, 3 to 4 minutes, or until browned and slightly softened. Add the chopped garlic; season with salt and pepper. Cook, stirring frequently, 30 seconds to 1 minute, or until lightly browned. Turn off the heat; carefully stir in the remaining vinegar. Using the back of a spoon, carefully press down on the tomatoes to burst.
Transfer the cooked bacon to a cutting board; halve each piece. Assemble the sandwiches using the bread, cooked tomatoes, halved bacon, and grated monterey jack; season with salt and pepper. Rinse and wipe out the pan used to cook the tomatoes.
In the same pan, heat 1 tablespoon of olive oil on medium until hot. Add the sandwiches; loosely cover the pan with foil. Cook 2 to 4 minutes per side, or until lightly browned and the cheese is melted (if the pan seems dry, add a drizzle of olive oil before flipping). Transfer to a cutting board; immediately season with salt. Carefully halve on an angle. Serve the cooked sandwiches with the finished broccoli on the side. Enjoy!
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