Ingredients
Pot Roast:
- 1 boneless beef chuck eye roast (about 3 1/2 pounds)
- Kosher salt and freshly ground black pepper
- 2 tablespoons vegetable oil
- 1 medium onion, roughly chopped
- 1 tablespoon dried Italian seasoning
- 2 teaspoons crushed red pepper
- 6 cloves garlic, roughly chopped
- 1/2 cup dry red wine
- 3 cups beef stock
- 2 sprigs fresh thyme
Sweet Peppers:
- 4 green bell peppers, seeded and cut into strips
- 2 tablespoons olive oil
- 1 teaspoon granulated garlic
- Kosher salt and freshly ground black pepper
Sandwich Build:
- 4 soft, hinged sub or hoagie rolls
- Homemade Hot Giardiniera, recipe follows
Directions
For the pot roast: Preheat the oven to 300 degrees F and position a rack in the middle position.
Liberally sprinkle the entire roast with salt and pepper. Heat the oil in a Dutch oven over medium-high heat. Brown the roast on all sides until golden and caramelized; reduce the heat if the fat begins to smoke. Transfer the roast to a plate and reduce the heat to medium. Add in onions and saute, stirring occasionally until just beginning to brown, 8 to 10 minutes. Add the Italian seasoning and crushed red pepper and saute until fragrant. Add the garlic and saute until fragrant, about 30 seconds. Deglaze with the red wine and cook until the alcohol smell is diminished. Add in the stock and thyme and bring to a simmer. Adjust the seasoning of the jus. Place the roast back into the pot with any accumulated juices and place in the oven. Cook the roast, turning every 30 minutes, until very tender, 3 1/2 to 4 hours. Increase the oven heat to 350 degrees F.
Transfer the roast to a cutting board and tent with foil. Strain the jus through a fine mesh strainer into a bowl and return back to the pot. Bring to a simmer and adjust the seasoning if necessary. Once cooled a bit, pull the meat into smaller chunks and reserve for the sandwiches.
For the sweet peppers: Toss the pepper strips with the oil, granulated garlic and salt and pepper on a baking sheet. Bake, stirring halfway through, until lighter in color and soft, about 20 minutes.
For the sandwich build: Simmer the jus until very flavorful and hot. Place some beef on a roll, then some sweet peppers and then some Homemade Hot Giardiniera. Take the whole sandwich and quickly dunk in hot jus. Using 2 hands, go the hell to town.
Homemade Hot Giardiniera:
- 1/4 cup table salt
- 1 cup small-diced carrots
- 1 cup tiny cauliflower florets
- 4 to 8 serrano peppers, sliced (depending on heat level desired)
- 2 cloves garlic, minced
- 1 stalk celery, diced small
- 1 red bell pepper, diced small
- 2 cups canola oil
- 1 tablespoon dried oregano
- 1/2 teaspoon freshly ground black pepper
Combine 2 cups water and the salt in a glass or non-reactive bowl. Mix until the salt is dissolved. Add the carrots, cauliflower, serranos, garlic, celery and bell pepper to the salt water and stir to combine. Cover and refrigerate overnight.
Day 2, drain and rinse the vegetables. In a clean bowl, mix together the oil with the oregano and pepper. Add the vegetables and mix to combine. Allow to marinate overnight. Giardiniera will only get better with time. After 2 days at the most in the bowl, you can place in air-tight mason jars and keep in the fridge for at least 2 to 3 weeks. Yield: 3 to 4 cups.

















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By maxeyk_12276492
Woodsboro, MD
on May 01, 2012
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I'm neither from Chicago nor Italian, but had one of these sandwiches from an authentic Chicago establishment years ago and have since been searching for a good recipe. This is it, and it's even simpler than most others I've come across! Other recipes for Chicago Italian Beef Sandwiches typically say to soak the cooked meat for a few days in the au jus before serving, so I cooked mine the day before, sliced it fairly thin, and soaked it overnight in the fridge before heating up and serving the next day. I'll definitely do the same next time I make this, as the soaking process really brought moisture into what was otherwise fairly dry meat. I don't care for gardiniera on it so just used jarred mild Peppadew peppers (they are worth the price! on the sandwiches and thought the sweet/hot combo was perfect. Great food to have on hand for busy weekends.
By mcoylern_868569
endicott, NY
on April 22, 2012
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OMG!!!! Probably the best sandwich you'll ever eat!!!! I have made this a few times now and have learned to double the broth the roast cooks in because it does cook down a lot. The flavor of the juice is sooooo good and the beef just as tender as can be. On all of Jeff's recipes, I cut back on the cayenne pepper. He adds too much for my taste. Love to see what Jeff is going to make week to week.
By anitajohnson37_...
Yorba Linda, CA
on March 26, 2012
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Delicious is an understatement!!! The most tender pot roast I've ever made. I left out the italian seasoning, and also, the red pepper,(to make it child friendly... and doubled the rest of the liquid ingredients as well as the garlic and onion in the recipe. We had pot roast the first night, (over mashed pots, The flavor of the juice was through the roof. Again had leftovers a few days later as sandwiches, and still had enough to freeze. A month later, thawed it out, and added veggies and served up a Beef Stew. Jeff...from one Italian to another... Di prim`ordine!!
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