Sprinkle steak with ¾ tsp salt and the pepper. In large, heavy skillet, heat 1 tbsp of the olive oil over medium-high until shimmering. Add steak and cook until instant-read thermometer inserted in centre reads 145°F for medium-rare, about 4 minutes per side. Transfer to cutting board; tent with foil.
Immediately reduce heat to medium; add remaining oil and garlic and fry, stirring, until light golden, about 1 minute. Sprinkle in hot pepper flakes and cook until colour changes from red to burgundy, about 10 to 20 seconds. Stir in wine; cook and reduce by half.
Meanwhile, add tomatoes and juices to a bowl; using hands, crush tomatoes into chunks. Add ½ cup water into can and swirl before adding to tomato bowl. Carefully add tomato mixture into pan and stir in the remaining salt, oregano and cannellini beans. Bring to a low boil and cook for 10 minutes.
To serve, toss arugula with oil, lemon juice and salt in a large bowl. Cut steak into ½-inch thick slices. Keep snugly together and place over tomato and bean mixture. Arrange the arugula salad beside the steak and top with parmesan.
Serve family-style – in the pan with four shallow bowls – allowing diners to help themselves.