I have been trying to recreate Chicagos famous Italian beef sandwiches for years but have never been able to master it. When I saw Jeff Mauro do it, first on food network star and then on his show sandwich king I knew this recipe was a keeper
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 Take the whole sandwich and quickly dunk in hot jus.