Heat a large Dutch oven over medium-high heat and add olive oil. Season beef chuck roast with salt and pepper, then sear for 4-5 minutes per side until browned.

Remove the roast and set aside. In the same pot, add onions and garlic, sautéing for about 5 minutes until translucent.

Deglaze the pot with red wine, scraping up browned bits. Simmer for 2-3 minutes until slightly reduced.

Add beef broth, diced tomatoes, and Italian seasoning. Return the roast to the pot, cover, and simmer for 2 hours, until fork-tender.

In a separate saucepan, melt butter, add Arborio rice, and toast for 2-3 minutes stirring frequently.

Gradually add warmed chicken broth to the rice, one ladle at a time, stirring constantly for 20-30 minutes until creamy and al dente.

Stir in grated Parmesan cheese until melted. Keep the risotto warm on low heat.

Slice the pot roast and serve with risotto, garnished with fresh parsley.