Step 1

Place a wire rack inside a large rimmed baking sheet. Core tomatoes by cutting out a small cone-shaped wedge from around stem. Slice tomatoes in half from top to bottom. Slice half of tomato halves ½" thick. Slice remaining halves into ½"-thick wedges. Set tomato pieces on prepared rack. Sprinkle on both sides with salt; let sit 10 minutes.

Step 2

Cook garlic, chile, and oil in a large high-sided skillet over medium-low heat, stirring until fragrant, about 2 minutes. Add tomatoes, one at a time,  into a snug single layer with little overlap (like filling a fruit tart). Leave out any that don’t fit. Scatter olives over top of and in between tomatoes. Increase heat to medium-low so oil is simmering very lightly, cover, and cook 2 minutes. Uncover and sprinkle oregano over tomatoes. Cover again and cook tomatoes until warmed through and very fragrant but not falling apart, 3–5 minutes more.

Step 3

Remove pan from heat; set a platter that is the same size as the pan beside it. Lift pan and tilt so tomatoes, along with any liquid, slide out onto platter. Drizzle with vinegar and top with crumbled Cotija. Serve with bread, if using, for soaking up tomato juices.