Kent Rollins' Best Steak Sandwich

Howdy, y’all and thank you for stopping by the website. The key to a great sandwich is to pay attention to the details. Taking the time to dress up every single part of the sandwich is the key to making the best steak sandwich you’ll ever eat. I’ll list all of the tips and tricks I use to take a regular sandwich and make it an over-the-top favorite.

Caramelize the Onions

The best caramelized onions are not made by slicing the onions and tossing them into the hot skillet. Nope. Start by slicing a white onion into rings. Cover over well with about a tablespoon of salt and let sit for about ten minutes. The salt will help pull a lot of the juice out of the onion.

Get the cast iron skillet hot and add butter and olive oil. Stir in the onions until they are well-coated with the butter and oil, and then move to medium low heat and cover well. Simmer for about ten minutes.

Tip: Sprinkle salt over the onions and let sit for ten minutes before cooking to dehydrate them before caramelizing.

The onions should be well cooked down after the first ten minutes, but we want them extra tender. Turn the heat to low, stir well, and cook another 10-15 minutes until the onions have turned brown and are soft and sweet.

When the onions are just about done, add the thyme and garlic. Remove from heat after about one minute.

Beef Tenderloin

When choosing meat for a sandwich, always go with a tender cut. For a steak sandwich, the tenderloin is the best bet. Located in the upper back area, the tenderloin muscle doesn’t get a lot of use, which means it makes a sweet, tender piece of steak.

Infographic of Beef Cuts

I like to buy the whole tenderloin, and then cut out the filets myself. If you buy the whole tenderloin, you’ll want to cut the center out of it. This cut of beef needs to be somewhat symmetrical so the beef will cook evenly all the way through.

Start by seasoning generously all over with our original seasoning. Allow the steak to cool to room temperature, about 30 minutes.

Tip: The most common cooking mistakes are under-seasoning and over-cooking. Season well and use a meat thermometer to make sure you don’t over-cook.

Pre-heat the grill to about 400 but do so with the coals over to one side. Start by grilling the filet right on top of the fire. Move it around so all sides get a good char on, and then move to the indirect heat on the other side of the grill for around 12-15 minutes. Cover and cook until the internal temperature reads just at 100 degrees. Wrap in foil and let rest for 8 minutes. You’re ready to slice!

Toast the Bread

Slice a beefsteak tomato thick and place the slices on the grill. Use the rest of the olive oil to coat the insides and outsides of the bread and toast on the grill while the tenderloin rests. The flavor from the grill on the tomato and the toasted bread take this sandwich from good to amazing.

Assemble the Sandwich

Start by slathering both sides of the bread with the special sauce. Layer two-three thick slices of the filet and top with grilled tomatoes. Add some lettuce – arugula has a peppery taste and works well with the beef – and then top with the second piece of bread. Dig in before anyone else gets to it because these are going to get eaten fast.

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Best Steak Sandwich – Cowboy Kent Rollins

Prep Time 40 minutes
Cook Time 45 minutes
Total Time 1 hour 25 minutes
Servings 4 sandwiches

Ingredients

  • 1 large white onion
  • 2 tablespoons kosher salt divided
  • 2 tablespoons unsalted butter
  • 4 tablespoon olive oil or avocado oil divided
  • 6 sprigs fresh thyme
  • 1 large elephant ear garlic clove minced
  • 2 to 3 pound beef filet or tenderloin
  • 3 tablespoons Kent Rollins' Original Seasoning or seasoning blend of your suiting
  • 1 large beefsteak tomato
  • 4 hoagie buns
  • ½ tablespoon coarse ground black pepper
  • Arugula or butter lettuce for topping

Mayo Sauce

  • 6 tablespoons mayonnaise
  • 1 tablespoon french onion dip
  • 1 tablespoon spicy mustard
  • 1 tablespoon Worcestershire sauce
  • 1 teaspoon horseradish
  • ½ tablespoon coarse ground black pepper

Instructions

  1. Slice the onion into rings about ¼ to ½ inch thick. Sprinkle 1½ tablespoons of salt all over. Mix well.

  2. Remove the filet from the refrigerator at least 30 minutes ahead of time. Season well with Kent Rollins' Original Seasoning and set aside.

  3. In a small mixing bowl, combine all the mayo sauce ingredients and mix well. Chill in ice box while the meat and onions cook.

  4. Preheat the grill to 400, with coals on one side.
  5. Meanwhile, place a large cast iron skillet over medium low heat and then add the butter and 2 tablespoons of the oil. When the skillet is hot, add the onions, stir well and cover.
  6. After 10 minutes, stir well again, and place the lid back on and cook for another 5 minutes. Remove the lid, turn the heat down to low and continue to cook for another 10 to 15 minutes or until the onion has a rich brown color. Add the thyme and garlic. Cook for another minute, stirring occasionally. Remove from the heat and set aside.
  7. Place the filet over direct heat and sear all sides, until you get a good char – about 5 minutes. Using tongs, roll the meat to get all sides evenly cooked.
  8. Move the filet to the indirect heat side of the grill. Close the lid and cook for another 12 to 15 minutes or until the internal temperature is 100 degrees F. Remove from the grill. Tent with aluminum foil and let it rest for about 8 minutes.
  9. Cut the beefsteak tomatoes into slices and place on the grill. Cook for about 2 minutes each side. Remove from the grill and set aside.
  10. Slice the bread in half and use the remaining oil to coat both sides. Season with salt and pepper and place on the grill.
  11. Cook over direct heat for about 2 minutes or until there are good grill marks on the bread.
  12. Spread a generous amount of the mayo sauce on both sides of the bread. Place two – three slices of meat, tomato, and onion mixture. Top with lettuce. Place bread on top and serve.