Chicagoan-Italian Roast Beef Heroes

Pile juicy beef slowly simmered in wine high onto a hero roll and top with cheese, peppers and homemade giardiniera. Hats off to Chicago for the inspiration!


  • 1 jar store-bought giardiniera or prepare the below recipe 2 days prior to serving the heroes

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 chili peppers or banana hot peppers, sliced into thin rings
  • 2 cups blanched cauliflower florets
  • 2 carrots, peeled and sliced 1/4-inch thick
  • 2-3 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 extra virgin olive oil (EVOO)
  • 1 cup Sicilian green olives, pitted and chopped

For the sandwiches:

  • 1 beef chuck roast (3-3 1/2 pounds)
  • Kosher salt and coarse black pepper
  • 4 tablespoons extra virgin olive oil (EVOO), divided
  • 3 onions, 2 chopped and 1 thinly sliced
  • 6 cloves garlic, sliced
  • 2 large fresh bay leaves
  • A small handful of 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
  • 4 cups beef stock (32 ounces)
  • 1 can diced tomatoes (15 ounces)
  • 4 cubanelle peppers 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


For the giardiniera, place the 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 a dressing of garlic, oregano, celery seed, vinegar and oil. Drain the salad and toss with the dressing and olives.

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

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

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

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Rachael Ray