Brown Sugar Bourbon Steak Sandwiches

Red meat, cheese, sugar and booze. It’s like vice city up in here today. It’s everything you are not supposed to eat, slathered between two pieces of bread. We’re going to food hell in a food hand basket! (What does that even mean?) At least we are going to be eating some good sandwiches on the way.

What I learned from this:

  • Slice the steak against the grain! DOH!
  • The whiskey and the brown sugar combined into this awesome caramely sauce in the pan. I bet I could use this information to make something else delicious. Whiskey caramel sauce? Noted for future reference.


The deets:

1/4 cup brown sugar

1/4 cup bourbon or some other whiskey (I used Maker’s Mark)

1 tbs crushed red pepper

1.5 lb flank steak

2 tbs canola oil, divided

2 large shallots, sliced thin

2 oz of cheese of your choice. I used a nice, sharp cheddar.

  1. Whisk marinade ingredients together. Marinate steak for 30 minutes – 3 hours.
  2. Meanwhile, in a cast iron skillet, cook the onions in 1 tbs of the oil on medium-low heat until they begin to brown and caramelize.* Once they are finished, remove from heat and wipe out the skillet.
  3. Heat skillet to very hot, add remaining tbs of oil and sear steak for 4 minutes on each side for medium-rare. Keep in mind it will cook a little longer when you grill the sandwich. So if you like it more rare, cook it on the stove for less time. If you like it more done, cook it a lil longer. Your call.
  4. Remove steak from pan and allow steak to rest for 10 minutes.
  5. Slice steak and layer between two slices of bread with sandwich fixings of your choice. In this case, the caramelized shallots and cheddar cheese.
  6. Grill the sandwich on a panini press or similar apparatus for 3 minutes, or until your cheese is melty.


*A note about caramelizing onions: Keep ’em on real low heat, and let them cook for a long time. It can take a solid 30 minutes to an hour, depending on the thickness of your slices. I know, it sucks. That’s a really long time. You don’t have to disturb them too much, so you can go watch that March Madness game while they are cooking, if you want.  Just check on them periodically and make sure they aren’t burning. If the pan gets too dry, you can add a little water. Don’t be tempted to turn up the heat. You’ll just get burnt onions. If you don’t have that kind of time at your disposal, you can just omit them from this recipe. I won’t tell anyone.


But I put it on whole wheat bread. Bread that you  may remember from this post. Turns out the skinny bread slices worked out okay for these sammies. And look at Ginger trying to act nonchalant about whether or not she will get some steak. FYI, She didn’t. I’m an asshole like that. I don’t feed her people food. It’s bad for her little doggie digestion.

So maybe she’s actually pouting. She does look a little pissy.


The shallots came from Tuscarora Organic Growers Co-op.

The cheese came from Clover Creek Cheese Cellar.

The steak came from heaven.

4 responses to “Brown Sugar Bourbon Steak Sandwiches

  1. Poor Ginger. People food never killed anyone, oh wait, hmmmm…………..if she is like most Basenji blooded doggies, she will find a way to get her own taste in. Did I say how I lost half my sandwich last week to a certain critter 😉

    • You’re lucky you didn’t lose the whole sandwich! Ha ha. Ginger is actually a funny little dog in that she isn’t always that interested in people food. Of course steak is a different story. She would definitely take that from your plate. Overall, though she sticks to her puppy chow! We do try to avoid giving her lots of people food, but of course, we sneak in a few treats here and there. 🙂

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