1 pint of cherry tomatoes
4 medium-size shallots, peeled and quartered
1/4 cup plus 3 tablespoons extra virgin olive oil (EVOO), divided
Salt and coarse black pepper
2 cloves garlic, crushed
3 sprigs of fresh thyme (dried will work if fresh is unavailable)
2 New York Strip steaks (about 10- to 12-ounces each)
1 1/2-2 pounds medium to large Yukon gold potatoes
1 tablespoon Dijon mustard
2 teaspoons Worcestershire sauce
2 tablespoons sherry vinegar
2 large handfuls of watercress, cleaned and trimmed of thick stems
Pre-heat oven to 400ºF. On a baking sheet, combine the tomatoes with the quartered shallots. Drizzle with a tablespoon of EVOO and season with salt and freshly ground black pepper. Add the garlic cloves and sprigs of thyme to the baking sheet, transfer to the oven and roast for about 10-15 minutes, until the tomatoes have burst and the shallots are slightly tender.
While the tomatoes and shallots are cooking, take the steaks out of the fridge to bring them up to room temperature. Place the potatoes in a large pot and add enough cold water to cover by two inches. Place the potatoes over high heat and bring them to a boil, add some salt, and cook for 10-12 minutes, until tender -- you should be able to pierce them easily with a knife. Drain the potatoes and let them cool enough so that you can handle them. Once cool, cut the potatoes into half-inch slices and set aside.
Once the potatoes are cooking, start the steaks: Pre-heat a stainless steel sauté pan or cast iron skillet over medium-high heat until it is screaming hot. While the skillet is heating, pour about a tablespoon of EVOO over each steak and season on both sides with salt. Press a generous amount of coarsely ground black pepper into one side of the steaks. Arrange the steaks, pepper side down, in the screaming hot skillet and do not move them. Cook for 2-3 minutes per side for medium-rare or until desired doneness. Transfer the steaks to a plate and cover loosely with aluminum foil to rest for about 5 minutes. For the Au Poivre dressing, combine the Dijon mustard, Worcestershire sauce, sherry vinegar, salt and pepper in a bowl. Whisk remaining 1/4 cup of EVOO in a slow, steady stream. Place a few sliced potatoes on the plate along with the steaks and a handful of watercress and pour the Au Poivre dressing over everything.