In a large resealable plastic bag, combine the wine, vinegar, garlic and rosemary. Season the steaks with salt and pepper and add to the marinade. Refrigerate the steaks overnight.
Preheat the oven to 375 degrees .
Soak the potatoes in salted water in a large bowl for a few minutes. Drain and pat dry. Toss the potatoes with 3 tbsp. EVOO and the thyme; season with salt and lots of pepper and toss again. Spread out on a foil-lined baking sheet and bake for 20 minutes. Remove from the oven and let cool to room temperature. Increase the oven temperature to 450 degrees .
Return the potatoes to the oven and roast until deeply golden and crispy, about 15 minutes.
Heat a cast-iron or ovenproof skillet over medium-high. Pat the steaks dry and coat evenly with 2 tbsp. EVOO. Place the steaks in the preheated skillet and brown on each side, then pop in the oven to cook to medium, about 5 minutes. Let the steaks rest before serving with the potatoes and arugula-tomato salad.