Preheat a grill or grill pan to medium-high. Drizzle EVOO over the steaks and season with salt and pepper. Grill the steaks, turning twice, 12 to 15 minutes for medium-rare. Let rest for 5 minutes.
In a large skillet, cook the bacon over medium-high heat until crisp. Drain on paper towels and let cool. Pour off all but about 1 tablespoon of bacon drippings from the skillet, then add the leeks, cover and cook over medium heat, stirring often, until wilted, about 5 minutes. Season to taste with salt and pepper; set aside.
Crumble the bacon and transfer half to a food processor. Add the Worcestershire sauce, vinegar, mustard, some pepper and a splash of water. With the machine on, pour in the 1/2 cup EVOO in a steady stream.
Arrange a bed of the romaine and tomatoes on each of 4 plates. Slice the steak against the grain and layer over the tomatoes. Scatter the leeks over the steak and pour the bacon dressing on the salad. Top with the remaining crumbled bacon.