Preparing the Roasted Garlic Aioli

1. Roast the Garlic: Start by preheating your oven to 400°F (200°C). Slice off the top of the garlic bulb, exposing the individual cloves. Drizzle with a bit of olive oil and wrap the bulb in foil. Roast in the oven for about 30-35 minutes, until the garlic is soft and fragrant. Once roasted, allow the garlic to cool for a few minutes before squeezing the soft garlic cloves out of their skins.
2. Make the Aioli: In a food processor or bowl, combine the roasted garlic cloves with 1 cup of mayonnaise, 2 tablespoons of olive oil, 1 tablespoon of lemon juice, 1 teaspoon of Dijon mustard, ½ teaspoon of salt, and ¼ teaspoon of freshly ground black pepper. Blend or whisk until smooth and creamy. Taste and adjust the seasoning if needed, adding more salt or lemon juice if desired. Set the aioli aside, or refrigerate it until you’re ready to assemble the sandwich.

Cooking the Beef

3. Prepare the Beef: Heat 2 tablespoons of olive oil in a large skillet or Dutch oven over medium-high heat. Season the beef roast generously with salt and pepper on all sides. Sear the beef in the hot oil for 2-3 minutes per side until it develops a nice brown crust. This step will add depth of flavor to the final dish.
4. Add the Aromatics: Once the beef is seared, transfer it to a slow cooker. In the same skillet, add the minced garlic and sliced onion, cooking for 2-3 minutes until fragrant and softened. Then, pour in 2 cups of beef broth and 1 cup of red wine (if using). Add the dried oregano, basil, rosemary, crushed red pepper flakes (if using), and another pinch of salt and pepper. Stir to combine the seasonings and liquids.
5. Slow Cook the Beef: Pour the onion and broth mixture over the beef roast in the slow cooker. Cover and cook on low for 3-4 hours, or until the beef is tender and shreds easily with a fork. If you have more time, you can also cook the beef on high for 2-3 hours, but low and slow results in the best texture.
6. Shred the Beef: Once the beef is fully cooked, remove it from the slow cooker and let it rest for a few minutes. Use two forks to shred the beef into bite-sized pieces. If desired, you can also return the shredded beef to the slow cooker with some of the juices to keep it moist and flavorful until ready to serve.

Assembling the Sandwich

7. Toast the Buns: While the beef is resting, cut the Italian rolls or hoagie buns in half and lightly toast them in the oven or on a grill. Toasting the buns gives them a crispy texture that will hold up to the juicy beef and aioli without getting soggy.
8. Build the Sandwich: Once the buns are toasted, spread a generous amount of roasted garlic aioli on the bottom half of each bun. Pile the shredded Italian beef on top, allowing the juices from the beef to soak into the bread. If you prefer a bit of extra flavor, add some pickled peppers or giardiniera on top of the beef. You can also garnish with fresh basil or parsley for a pop of color and flavor.
9. Serve and Enjoy: Place the top half of the bun on the sandwich, press it down lightly to secure everything, and serve immediately. These sandwiches are great on their own or served with a side of crispy fries, a green salad, or roasted vegetables.