Preheat oven to 300F.
Slice the chuck roast into short rib-like pieces, about 3-5” rectangles. Season all sides generously with the 1 ½ tsp. salt and crushed black pepper. Dust evenly with the ¼ cup flour, shaking off any excess.
Place a large, oven-safe dutch oven, over medium high heat. Add the olive oil to warm up for 1 minute, until glistening.
You may need to work in 2-3 batches to prevent overcrowding in the dutch oven which will prevent a golden crust from forming on the beef. Add the seasoned chuck roast to the hot oil to sear untouched for 4-5 minutes, then flip with tongs to sear untouched 4-5 more minutes. A deeply golden crust should form on both sides.
If you worked in batches, add all meat back into the dutch oven. Reduce heat to medium before adding the red wine. Let cook for 1 minute, then add the beef stock.
Add the garlic head, fresh rosemary sprigs, brown sugar, bay leaves, Worcestershire sauce, ground cloves, and remaining 1 tsp. fine sea salt. Stir to combine.
Bring to a boil, then cover with the lid to slow cook in the oven for 3 ½ - 4 hours, until meat
shreds easily between two forks.
In a small bowl, whisk the remaining 2 tbsp. flour and water until smooth.
Use a slotted spoon to transfer all meat and veggies from the dutch oven to a separate bowl. Place the dutch oven over medium high heat. Stir in the flour-water slurry.
Bring to a boil, then reduce heat to simmer for 25-30 minutes, until sauce has reduced by half, a little glossy, and slightly thickened up. Stir occasionally to prevent any burning along the edges.
Stir the butter into the simmer sauce.
Either add the beef and veggies back into the simmer sauce to coat or serve the simmer sauce over the beef.
If prepping in advance, add the meat back into the simmer sauce, let cool to room temperature, then store in the fridge for up to 2 days in advance. Reheat over medium on the stovetop with a splash of beef stock and covered with the lid until meat is warmed through, about 10-15 minutes.