Step 1

Preheat the oven to 400 degrees F.

Step 2

In a large bowl, add the chuck roast pieces, the salt, and the pepper and toss to coat.

Step 3

In a separate bowl, add the brown sugar, the bourbon, the garlic, the Thai spices, the Greek spices, the red chili flakes, the extra-virgin olive oil, the tomato paste, the pepperoncini peppers, and 1 cup of the water and whisk to combine.

Step 4

Pour the sauce mixture over the beef and use your clean hands to work the sauce into the meat, about 2 minutes.

Step 5

Let the meat marinate for 30 minutes.

Step 6

In a large roasting pot over medium-high heat, add the canola oil.

Step 7

Transfer the meat from the marinade using tongs and coat the pieces in the flour. Do not discard the marinade.

Step 8

Add the meat to the hot oil and sear on all sides, about 2-3 minutes per side.

Step 9

Reduce the heat to low.

Step 10

Slowly add the marinade and 1 1/2 cups of the water to the beef in the pot.

Step 11

Cover the pot tightly with a lid and roast for 1 hour.

Step 12

Reduce the oven heat to 300 degrees F.

Step 13

Check the beef mixture to see if it needs additional moisture, adding the extra water or the beef broth as needed.

Step 14

Roast until the meat shreds apart with a fork and reaches an internal temperature of 165 degrees F, about 1 hour 30 minutes.

Step 15

Check the gravy in the pot for thickness, and thin it out as desired with the extra water or the beef broth.

Step 16

Serve.