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Playing Chicagoan-Italian Roast Beef Heroes


  • 1 jar store-bought giardiniera, or prepare the below recipe 2 days prior to serving the heroes
For the giardiniera:
  • For the giardiniera:
  • 1/4 cup Kosher salt
  • 1 small red sweet bell pepper or green cubanelle pepper, seeded, quartered and cut into 1/2-inch slices
  • 2 small finger peppers, Fresno chilies or banana hot peppers, sliced into thin rings
  • 2 cups blanched cauliflower florets
  • 2 carrots, peeled and sliced 1/4-inch thick
  • 2 to 3 ribs celery with leafy tops, chopped into 1-inch pieces
  • 2 large cloves garlic, grated or minced
  • 1 teaspoon dried oregano or marjoram
  • 1 teaspoon celery seed
  • 1/4 cup white balsamic or white wine vinegar
  • 1/4 cup EVOO Extra Virgin Olive Oil
  • 1 cup Sicilian green olives, pitted and chopped
For the sandwiches:
  • For the sandwiches:
  • 1 3- to 3 1/2-pound beef chuck roast
  • Kosher salt and coarse black pepper
  • 4 tablespoons EVOO Extra Virgin Olive Oil, divided
  • 3 onions, 2 chopped and 1 thinly sliced
  • 6 cloves garlic, sliced
  • 2 large fresh bay leaves
  • A small handful thyme sprigs
  • 2 stems fresh rosemary
  • 1 1/2 teaspoons dried oregano or marjoram, half a palmful
  • 1 1/2 cups (1/3 bottle) dry red wine
  • 1 quart beef stock
  • 1 15-ounce can diced tomatoes
  • 4 cubanelle or 2 bell peppers, seeded, halved and thinly sliced
  • Deli sliced provolone cheese, optional
  • Italian-style hoagie rolls, 1 per person, split but not cut all the way through


Serves: 4-6 with leftovers



For the giardiniera, place salt in a bowl; add the vegetables and cover with cold water. Stir to combine and cover. Store for 2 days to brine. Whisk up dressing of garlic, oregano, celery seed, vinegar and oil. Drain salad and toss with dressing and olives.


For the beef, preheat oven to 325F and bring the meat up to room temperature. Heat a large Dutch oven over high heat with a turn of the pan of EVOO. Pat roast dry, season liberally with Kosher salt and pepper. In the hot oil, brown roast evenly all over and remove. Wipe pan out and reduce heat to medium. Add another 2 turns of the pan EVOO, 2 tablespoons, add chopped onions, garlic and herbs, and stir. Cook 5-6 minutes to soften, add wine to deglaze pan and reduce 5 minutes more. Add stock and tomatoes, and stir. Add the roast back into pot, cover and roast in oven 3-3 1/2 hours to tender. Remove meat and let rest. Strain sauce and return to pot. Turn heat on high and reduce by half, about 10-15 minutes.


Meanwhile, heat 1 tablespoon EVOO in skillet over medium to medium-high heat. Add cubanelle or bell peppers and sliced onion, and season with salt and pepper. Soften 10-15 minutes. Add some of the meat sauce to the onions and peppers to deglaze.


Dip thinly sliced or shredded beef in sauce and stuff the hoagie rolls. Top with cheese, peppers, giardiniera.