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Heat olive oil over medium-high heat. Sprinkle salt and pepper on all sides of the chuck roast. Brown the chuck roast in the olive oil on all sides. Transfer to crockpot. Pour beef broth, Peperoncinis and juice, Hot Cherry Peppers, and crushed tomatoes on top of the roast. Cook on low for 8 hours.
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If you have time, refrigerate for at least a couple hours to allow the fat to harden at the surface. Scrape that off and trash it. (If you don't have time, get rid of the fat that you can and proceed.) Use two forks to shred the meat and return it to the cooking liquid. Heat on the stovetop until hot.
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To serve, put a pile of meat on bottom of a roll, top with provolone cheese, and the top of the roll. Serve with a small bowl of the cooking liquid to dip.