Preheat oven to 325°.
Combine first 3 ingredients, stirring with a whisk.
Heat a large Dutch oven over medium-high heat. Sprinkle beef with 3/4 teaspoon salt and 1/4 teaspoon black pepper. Coat pan with cooking spray. Add beef to pan; cook for 8 minutes, browning on all sides. Remove beef from pan; cover and set aside.
Add 1/2 teaspoon salt, 1/4 teaspoon black pepper, onion, sugar, and 1 teaspoon thyme to pan. Cook 20 minutes or until onions are tender and golden brown, stirring occasionally. Add garlic, carrots, and celery; cook 5 minutes, stirring occasionally. Place beef on top of onion mixture; pour wine mixture over beef. Cover and place in oven.
Bake at 325° for 1 3/4 hours.
While beef mixture cooks, place potatoes in a large bowl. Add 3/4 teaspoon salt, 1/4 teaspoon thyme, oil, oregano, and red pepper; toss to coat. Arrange in a single layer on a jelly-roll pan coated with cooking spray.
Remove beef from oven; turn beef over. Place potatoes on lower rack in oven. Cover beef; return to oven. Bake potatoes and beef at 325° for 45 minutes or until beef is tender. Remove beef from oven; cover and keep warm. Increase oven temperature to 425°. Place potatoes on middle rack in oven; bake at 425° for 15 minutes or until crisp and edges are browned.
Remove beef from pan; cut across the grain into thin slices. Serve with onion mixture and potatoes. Sprinkle with parsley.