For the Steak: Mix together 1/4 cup of olive oil and the garlic and let rest for 30 minutes. Preheat broiler. Brush both sides of the bread with the garlic oil, place on a baking sheet and broil for 1 to 2 minutes on each side, until lightly golden brown. Heat grill pan over high heat until smoking. Brush steak on both sides with the remaining 2 tablespoons of olive oil and season with salt and pepper to taste. Grill for 4 to 5 minutes until golden brown on 1 side, turn over, reduce heat to medium and continue cooking to medium-rare doneness, 5 to 6 minutes. Remove from heat, let rest 10 minutes and slice into 1/4-inch thick slices.
For the Tomato-Black Olive Relish: Combine all ingredients in a bowl.
To assemble: Place arugula on 4 slices of toast. Top with several slices of steak and a large spoonful of relish. Top with the remaining bread slices.
Skillet Fries: Heat olive oil in a medium cast iron skillet over medium heat. Add onions and cook until soft. Add peppers and garlic and cook for 3 to 4 minutes. Add potatoes and cook until golden brown, season with salt and pepper.