Preheat oven to 300F.
Slice the chuck roast into large chunks for easier searing. Season all sides with the salt and black pepper. Dust with flour and shake off any excess. Set aside.
Place a dutch oven over medium high heat. Add the olive oil to warm up for 1 minute, until glistening.
Sear the beef for 2-3 minutes untouched on two sides, until deeply golden and browned. If needed, work in two batches to prevent overcrowded the pot.
Reduce heat to medium, then add the sliced garlic and fresh rosemary sprig.
Add the red wine and 2 tbsp. butter to de-glaze the pot.
If you'd rather not caramelize the onions, add the onions.
Add the beef broth and worcestershire sauce. Make sure the beef is submerged in the beef broth.
Cover with the dutch oven lid to slow cook in the oven for 2.5-3 hours, until very tender.