Season the steak with salt and pepper.
Start by blanching tomatoes or using canned crushed tomatoes.
Heat the olive oil in a large skillet over medium-high heat.
Add the steak to the skillet and sear until browned. This will take about 2 minutes per side. Transfer the steak to a plate.
Press the garlic cloves into the skillet.
Once the garlic starts to sizzle and becomes fragrant, add the tomatoes and cook for about 4 minutes.
Add the sliced olives, oregano, and 3/4 cup water and stir to combine.
Once the sauce is rapidly simmering, add the steak back into the skillet.
Cook for about 3 minutes on each side for medium rare.
Remove the steak and set on a cutting board where you will let it rest for about 5 minutes before slicing it.
While you wait, continue simmering the sauce until thickened. It should take about 3 to 5 minutes.
Thinly slice the steak against the grain and divide among plates.
Top with the tomato sauce.