Pat meat dry with paper towels, then generously season the roast with salt and pepper. Heat a large dutch oven over high heat for 2 minutes. Add the olive oil to the pan. Once the oil begins to shimmer, sear the meat, turning to cook all sides evenly (About 4-6 minutes per side.) Take care not to turn the meat too soon or it will separate. Wait for it to easily releases from the bottom of the pan. Once finished, set the roast aside.
With the dutch oven still over medium heat, add onions, cook until onions are soft and translucent, about 5 minutes. Add the garlic and sauté for 3 minutes longer.
Add the red wine, beef stock and 1 sprig of thyme. Bring to a simmer and add roast back into the pan. Top with drained cherries, the second sprig of thyme, quartered shallots and 1 tablespoon of fresh black pepper. Cover and cook in oven for 2 hours, or until beef is tender and falling apart.