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Grilled Flank Steak Sandwich, with Roasted Tomato-Garlic ‘Jam’ and Gorgonzola Butter

Main Course, Sandwich
American, Californian


Ingredients 1

1 large flank steak, about 2 lbs.
½ gallon water
1 cup soy sauce
¼ cup sugar
2 tbsp. garlic, minced
1 tbsp. freshly ground black pepper
2 tbsp. fresh rosemary, chopped
Plain vegetable oil
More Salt and pepper
6 large sandwich rolls, (or baguettes cut into 1/3’s)
Tomato-Roasted Garlic Jam, (see below)
Gorgonzola Butter, (see below)
Fresh arugula, (or other greens)


  1. STEP 1:
    BEGIN RECIPE: Mix together the water, soy sauce, sugar, garlic, rosemary and pepper and stir till the sugar has dissolved in a large capacity oblong container. Place the flank steak into the brine, cover the container and place into your refrigerator for about 4 hours. If steak is not completely covered with the brine solution, turn it over about halfway through brining time. Make the jam and butter while the steak is brining.
  2. STEP 2:
    FOR JAM: 10 Roma tomatoes Olive oil Salt and pepper 1 head roasted garlic (see below if you’d like to make your own) 2 tbsp. fresh thyme leaves, chopped
  3. STEP 3:
    Preheat your oven to 425 degrees F. Rinse, dry and core the tomatoes. Next cut them in half from top to bottom. Use your finger to reach and remove all of the seeds. Place all prepped tomatoes in to a large bowl and pour a few spoonfuls of olive oil over them and then sprinkle them with a large pinch of salt. Next, place a piece of foil onto a sheet pan and place the tomatoes, cut side down, onto the foil.
  4. STEP 4:
    Roast the tomatoes for about 10 minutes or until their skins are beginning to separate. Remove the tomatoes from the oven and turn the heat down to 325 degrees F. Remove the skins from the tomatoes and discard. Return the tomatoes to the oven and slow-roast for about 40 minutes. Take tomatoes out of the oven and turn them over. Return the tomatoes to the oven and continue to slow-roast for about another half hour. Tomatoes are done when they are shrunken down, browned here and there and their juices have mostly evaporated. Remove from oven and cool to room temperature.
  5. STEP 5:
    Roughly chop the roasted tomatoes and place them in to a medium mixing bowl. Add the roasted garlic cloves, salt and pepper to taste, and the thyme. Mix the ingredients together evenly. Taste and correct seasonings and/or add olive oil as desired. Makes about 1 ½ cups jam. (This jam can freeze- place it into an airtight container and pour a thin layer of olive oil over the top. Keeps 2-3 months when frozen)
  6. STEP 6:
    FOR GORGONZOLA BUTTER: 2 sticks butter, at room temperature 4 oz. Gorgonzola cheese, at room temperature 1 tsp. coarsely ground black pepper 1 tsp. fresh rosemary, very finely chopped 1 tsp. fresh thyme, finely chopped 2 tbsp. fresh chives, finely chopped
  7. STEP 7:
    Place the butter and the cheese into the bowl of a mixer and mix and beat it until it is smooth. Add the remaining ingredients and mix until it is thoroughly blended. Remove the butter mixture to a container and set aside. (This compound butter can be refrigerated or frozen for 2 to 3 weeks). Makes about 1 ½ cups of Gorgonzola Butter.
  8. STEP 8:
    FINISH RECIPE: Cover a sheet pan with two layers of foil. Place a thick layer of paper towels on the foil. Remove steak from brine and place it on the paper towels and then cover it with more paper towels to dry the steak as much as possible. Discard the brine. Let steak sit for about 20 minutes.
  9. STEP 9:
    Prepare your grill and have it very hot (gas or charcoal). Remove the paper towels from the steak and discard them. Brush the steak all over with a light coating of the oil. Sprinkle lightly with some salt and then more generously with the pepper.
  10. STEP 10:
    Grill your rolls or bread, if desired, and set aside. Next, place the seasoned flank steak over very hot coals and grill for about 5 minutes or until nicely marked. Remove the first layer of foil and discard, leaving the clean second layer for the cooked steak. Flank steak should be rare to medium rare in the middle or it can be tough. So, turn steak over and grill on second side for just a few more minutes or until it is the doneness you prefer. Remove the steak from the grill and let it rest on the sheet pan for about 5 minutes.
  11. STEP 11:
    Prepare sandwich rolls while meat rests: Spread one side of the bread with a thick layer of the Gorgonzola Cheese. Spread the other half with a thick layer of the Roasted Tomato-Garlic Jam. Place some arugula over the jam. Next, slice the steak. This should be done against the grain and as thinly as you can for best results. Place a few slices of the steak over the arugula on each piece of bread or roll, top with the other half and serve right away. Makes 6 large sandwiches.
  12. STEP 12:
    Roasted Garlic* 4 heads garlic salt and pepper olive oil
  13. STEP 13:
    Slice the top portion of the garlic heads off with a serrated knife. The tops of most of the cloves inside should be exposed. Place the garlic heads on a large piece of foil. Sprinkle the tops of each garlic head with a little salt and pepper, then drizzle each of them with a little olive oil. Wrap the foil up and over the garlic heads so they are sealed tightly within. Put the garlic package on a baking pan and place it into a preheated 350 degrees F oven. Roast the garlic for approximately one hour, or until it is a nice golden brown color. Do not let the garlic become overly dark, it will become bitter. Remove package from oven and allow to cool. Garlic is now ready for use or freezing. If freezing, put garlic into individual closeable plastic bags.
*(This is a nice recipe to make large quantities of since it’s very little extra work to make enough to freeze!)


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