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Chicago Italian (roast) Beef Sandwich

I distinctly remember my first beef sandwich or maybe it is just the ONE that I remember best! It was made at a true hole-in-the-wall joint in the suburbs of Chicago. A few old Italian women ran the shop and served the best lunch in town. The smell of sliced roasted green peppers, onions, provolone cheese and garlic welcomed you when you walked in. The buns were perfectly crusty on the outside, nice and fluffy on the inside and stuffed with thinly sliced beef. I don't even remember if there was room to eat in the place. I just remember the anticipation of unwrapping that foil wrapped goodness, cheese oozing out and the sweet smell of caramelized onions.

While Michaelangelo's is no longer around, when we are visiting family in Chicago I like to order mine "wet" aka extra gravy and a lot of spicy giardiniera (Italian-style relish).


Preparation time: 15 minutes

Cook Time: 4-5 hrs

Chill Time(s): 8 hours & then 4 hrs minimum

Makes: 8-10 servings

1 small whole Pineywoods Beef Brisket (4-5 lbs)

Italian Beef Seasoning rub:

3 tsp, sea salt

2 tsp, black pepper (ground)

3 tsp oregano, dried

6 cloves garlic (or more if you love it!), finely chopped

1 quart Pineywoods beef stock

1 quart wine/beer (honestly, use whatever is on hand!)

1 medium white onion, thinly sliced

Optional Toppings:


Braised onions

Braised green pepper slices

Mozzarella/Provolone cheese

Please Note: This first step is one to do the night before you feast!

Mix Italian beef seasoning rub ingredients. Rub in seasoning until nicely coated. If you really want to up the garlic, a little trick is to pierce the meat in several places and stuff some garlic in! When finished, place the meat on a plate and back into the fridge overnight (or 8 hours minimum). This time will allow the flavors to marry.

Day of Feast

Preheat oven to 275F

Place the meat, beef stock and beer/wine into a heavy bottomed roasting pan and set in preheated oven. *Note: You do not want this brisket to be pull apart soft. It should have enough rigidity left for slicing thin. Roast for 4 hours.

Remove meat from liquid but save the gravy! Place meat and gravy in fridge to cool for about 4 hours.

When meat is thoroughly cooled, slice thinly. If you are using knives, slice as thinly as you can manage! That texture truly makes a difference and sets the Chicago Beef apart from the French roast beef sandwich! If you have an electric deli meat slicer all the better!

Place sliced beef and gravy in a heavy bottomed pan. Set heat to high/medium and warm the meat and gravy.

Cut Italian rolls down the side, scoop meat and gravy onto the roll and put all those toppings on.

Enjoy on a cold winter's night alongside steak cut potatoes fried in Beef tallow and an extra side "salad" of giardiniera!

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