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Prepare roast by patting dry and seasoning generously with kosher salt (at least 1 tsp per pound) and a sprinkle of black pepper. Let sit for a couple of hours or while you slice the onions and garlic.
Preheat oven to 325° and drizzle a large Dutch oven with olive oil over medium high to high heat. Sear meat on every side until golden brown. Remove from pot and set aside.
Reduce heat to medium. Add butter, onions, and a pinch of salt to pot and cook down for about 15-20 minutes until deep in color and very soft. Add garlic and cook for 1-2 minutes.
Add 2 tbsp flour and stir to coat onions and garlic evenly. Add in wine, bourbon, worcestershire, balsamic vinegar, and thyme. Return the meat to the pot and add two bay leaves.
Cover with lid and cook for 3.5-4 hours in the oven.
Shred meat carefully in pot or remove to a plate for shredding. Top with cheese and place under the broiler for a couple minutes until melted and bubbly.
Serve with creamy mashed potatoes and garlic bread.