Chicago Style Italian Beef Sandwich

One of our favorite dishes any time of the year, the Chicago Style Italian Beef lends itself to not only a great dinner but we will also show you how to transition it into a great passed hors d'oeuvres for an elegant party or fun backyard bbq.  The recipe does make quite a bit, and the leftovers freeze great (if you have any)!  My preference is to make the beef a day or two early as the flavors have more time to come together over a little time.  As for how spicy you like it, I usually will use mild peppers and mild pepperoncini but you can add the spicier variety as well as cherry peppers in place of bell peppers during the cooking stage for a kick.

Chicago Style Italian Beef Sandwich

4 pounds top round beef

4 Tablespoons dried Italian Seasoning (Lighthouse Freeze Dried Preferred)

1/2 teaspoon cayenne pepper

1 teaspoon paprika

1 teaspoon salt

1 teaspoon pepper

2 small sweet onions, sliced

1 head of garlic, cloves peeled and separated then smashed to crack them (approximately 3/4-1 cup)

2-4 cups beef stock (broth) - this will depend on the depth of your pot

2 cups red wine, Pinot Noir works great (approximately 1/2 bottle)

3 Tablespoons Worcestershire Sauce

2 bay leaves

1 small 8 oz jar mild sliced pepporncini peppers with juice (use about half the juice from the jar for cooking and reserve the peppers for garnish)

1 jar (15 oz) roasted sweet red bell peppers, sliced or roughly chopped and 1/2 juice reserved (use 1/2 the peppers for cooking and 1/2 for garnish)

Italian Bread Loaf or hot dog style rolls

4 Tablespoons olive oil (or use bacon fat if you have it leftover and on hand)

Combine the Italian seasoning, cayenne pepper, paprika salt, pepper.  Rub onto the beef and let rest for one hour at room temperature or up to overnight in the refrigerator. 

In a dutch oven, heat the oil (or bacon fat).  Add the beef and sear on one side about 5 minutes until nicely browned.  Flip the beef over and brown the other side, approximately 3-5 minutes, until browned.  While doing so add the onions and cook until softened.  Add the garlic during the last 2 minutes.  

Deglaze with wine then add the beefstock to cover, Worcestershire Sauce, bay leaves, 1/2 bell peppers with juice from 1/2 jar, and the pepporncini peppers juice from 1/2 the jar (use more or less pepporncini juice depending on how spicy you like your beef).  Bring to boil then transfer, covered, to a preheated 275 degree oven and cook 3 - 3 1/2 hours.  Remove from oven and allow meat to cool in the pot.  

Slice or shred the cooked beef and mix with the cooking liquid and cooked vegetables.  

Toast the bread rolls and fill with meat mixture.  Top with additional peppers if desired.