Prep Time (minutes)
Cook Time (hours)
3 pounds of beef chuck, fat trimmed, cut into 1¼ inch pieces
Kosher Salt and Freshly ground pepper
2 tablespoons of extra-virgin olive oil
6 shallots, thinly sliced ( 2 cups )
½ cup of dry red wine, such as Cabernet Sauvignon
1 can of whole peeled tomatoes, crushed (28 ounces)
1 Bulb fennel (12 ounces), cut into ½ inch wedges
1 sprig rosemary
2 strips orange zest (each 1 inch by 3 inches), plus orange wedges for serving
1 cup of pitted green olives, such as Castelvetrano (7 ounces)
Mashed potatoes, for serving
1 Season beef with salt and pepper. Heat a large skillet over medium-high. Add 1 tablespoon oil and half of beef, in a single layer; cook, turning a few times, until browned all over, 5 to 7 minutes.
2 Transfer to a 5-to-6-quart slow cooker. Repeat with remaining oil and beef. Add shallots and wine to skillet; cook, scraping up browned bits, until wine has almost evaporated, about 3 minutes.
3 Transfer to slow cooker; stir in tomatoes with their juices, fennel, rosemary, and zest. Cover and cook on high until meat is fork-tender, about 4½ hours.
4 Stir in olives; season with salt and pepper. Remove rosemary; serve, with mashed potatoes, orange wedges, and more pepper.