In a cast iron skillet, cook the bacon over medium-high heat for 10-12 minutes until crispy. Remove the bacon and leave 1 tablespoon of fat in the skillet.
Increase the heat to medium-high and add the tomatoes. Cook for 5-6 minutes until they are lightly charred and about to burst.
Stir in the garlic, reserved bacon, balsamic vinegar, brown sugar, black pepper, and salt. Cook for another 5-6 minutes until it thickens, then remove from heat and keep warm.
Let the steaks sit at room temperature. Season both sides with salt and black pepper.
Heat the skillet over high heat until it’s smoking. Add oil, then carefully place the steak in the skillet.
Cook the steak for 3 minutes on one side without moving it, then flip and cook for another 1-1.5 minutes. Repeat with any remaining steaks.
Slice the steak against the grain and serve with the warm tomato, bacon, and balsamic relish, topped with fresh torn basil.