4 bulbs garlic, remove 1 large clove from 1 bulb and peel it
Extra virgin olive oil (EVOO) for liberal drizzling, plus about 1/3 cup
8 sprigs rosemary, divided
2 large Russet potatoes
Grill seasoning, such as McCormick brand Montreal Steak Seasoning
8 slices smoky bacon
2 T-Bone steaks
Salt and coarse black pepper
1 shallot, peeled
2 teaspoons tomato paste
1 tablespoon Dijon mustard
1 tablespoon Worcestershire sauce
2 tablespoons red wine vinegar
1 heart of romaine lettuce, chopped
1 pint cherry tomatoes, halved
1 small red onion, chopped or quartered lengthwise, then very thinly sliced
1 generous bunch watercress or Upland cress, trimmed
Pre-heat the oven to 425˚F. Cut the ends off the bulbs of garlic to expose all of the cloves. Set them on a piece of foil big enough to wrap up and over the bulbs and drizzle with a little EVOO to lightly coat the garlic. Break two sprigs of rosemary in half and place a half-sprig on top of each garlic bulb; wrap and seal the foil into a pouch around the garlic. Place the garlic in the oven and roast for 45-50 minutes, until very tender.
Cut the potatoes into 10 wedges each, then cut the wedges into bite-size spears. Dress the potatoes in just enough EVOO to lightly coat the spears, a couple of tablespoons. Season liberally with grill seasoning and arrange on a baking sheet. Bake for 45-50 minutes, until tender and brown and crispy at edges, flipping only once. Remove the potatoes from the oven and cool.
Arrange the bacon on slotted broiler pan or on a rack arranged over a baking sheet and bake under the potatoes for 12-15 minutes, until crisp. Remove and cool, then chop.
Pre-heat a grill pan over medium-high heat or prepare an outdoor grill.
Take the chill off the steaks and allow them to come to room temperature. Pat the meat until very dry, then season with salt and pepper. Finely chop the remaining rosemary. Grate or finely chop the one large clove of garlic and mash the rosemary with the paste. Place in small bowl and cover with EVOO. Dress the meat with a brush of rosemary oil and grill for 8-9 minutes total for medium-rare doneness, basting occasionally with the rosemary oil. Grill for 12-15 minutes, turning occasionally, for medium-well doneness. Let the steaks rest to allow the juices to redistribute, then cut the meat away from the bone and thinly slice the steaks against the grain.
Grate the shallot into bottom of a salad bowl using a Microplane or the small side of a box grater. Place the tomato paste in a small cup and add a splash of very hot water, stir to combine and add to the bowl along with the mustard, Worcestershire sauce and vinegar. Whisk in the EVOO, about 1/3 cup. Season the dressing with salt and lots of pepper. Add the romaine, tomatoes, onion, watercress, potatoes and bacon to the bowl and toss to combine.
Arrange the salad on dinner plates. Dress the meat with any remaining rosemary oil. Divide the sliced meat into four portions and arrange alongside the salad with a head of roasted garlic to eat with the meat.