1/2cupextra-virgin olive oildivided plus more for steak
1cupwhole cherry or grape tomatoesplus more for salad
1mediumshallot roughly chopped
1mediumgarlic cloveroughly chopped
2tablespoonsbalsamic or sherry vinegar
1pinchunrefined cane sugar
kosher salt and Freshly ground black pepper
For The Boiled Potatoes:
1poundmarble potatoes or other tiny potatoes
For The Steak Salad:
2(8 ounce)New York Strip Steaks or Top Sirloin Steaks
1mediumbell pepperlarge dice
1/3cupthinly sliced celeryplus a few celery leaves for garnish
1/4cupthinly sliced green onions (aka scallions)
2tablespoonsfinely chopped fresh parsley, chives, or dilldivided for vinaigrette and garnish (optional)
Instructions
Make The Tomato Vinaigrette: Heat 1 tablespoon of the oil in a medium frying pan over medium-high heat until shimmering. Add tomatoes and sear, stirring occasionally, until the skins pucker and begin to color, about 2 minutes. Stir in garlic and shallot and cook until slightly softened, about 1 minute more.
Transfer tomato mixture to a small, deep mixing bowl, add vinegar, and purée with an immersion blender. Keep blending constantly with the immersion blender and slowly pour in the remaining oil, until well incorporated. Stir in 1 tablespoon of the herbs (if using) then season with salt and freshly ground black pepper, taste, and adjust seasoning as desired.
Cook The Potatoes: Place potatoes in a medium saucepan and cover with water. Bring to a boil over high heat then reduce to a simmer. Cook until potatoes are knife tender, about 15 minutes. Drain let cool slightly then halve.
Grill The Steaks: Meanwhile, heat the grill to medium high (about 400°F). Meanwhile, drizzle the steaks on all sides with a little oil, generously season with salt and pepper, and let come to room temperature while the grill is heating. Grill the steaks uncovered for 5 minutes per side for medium. Remove from the grill and let rest for 5 to 10 minutes. Cut into large dice and set aside.
Finish The Steak Salad: Combine the reserved steak, bell pepper, tomato, remaining 1 tablespoon of herbs (if using), celery, celery leaves, and scallions in a large, nonreactive mixing bowl. Halve the potatoes and add to the bowl. Toss with about 1/4 cup of the vinaigrette and season with salt and pepper as needed. Taste and add more salt, pepper, or vinaigrette, as desired. Serve immediately.