Season the beef chuck roast generously with salt and pepper.
In a large Dutch oven or heavy-bottomed pot, heat the olive oil over medium-high heat.
Add the beef roast and brown on all sides, about 4-5 minutes per side. Remove and set aside.
In the same pot, add the chopped onion, carrots, celery, and garlic. Cook, stirring occasionally, until the vegetables are softened, about 5-7 minutes.
Add the red wine to the pot, scraping up any browned bits from the bottom of the pan.
Return the beef roast to the pot and add the crushed tomatoes, beef broth, bay leaves, rosemary, thyme, oregano, and red pepper flakes (if using).
Bring the mixture to a simmer, then reduce the heat to low. Cover and let the pot roast braise slowly for 2.5 to 3 hours, or until the beef is tender and can be easily shredded with a fork.
Once the beef is tender, remove it from the pot and shred it using two forks.
Return the shredded beef to the pot and stir to combine with the sauce.
Taste and adjust the seasoning with salt and pepper as needed. If using, stir in the tomato paste, balsamic vinegar, and olives at this point.
Simmer uncovered for an additional 15-20 minutes to allow the flavors to meld.
Remove the bay leaves and discard.
Garnish with chopped fresh parsley before serving.
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