Season the beef medallions with salt and pepper. Wrap each medallion with a slice of bacon like a belt and secure with toothpicks.

Sear each medallion in a skillet over high heat until browned on the outside but still raw inside. This helps keep the meat juicy. (Do NOT wash the skillet, as you'll use it to make the red wine sauce.)

Once all the medallions are seared, place them on a baking sheet and bake at 350°F (175°C) for 30 to 45 minutes, depending on your preferred doneness.

Red wine sauce:

In the same skillet used to sear the medallions, add 1/2 cup red wine and scrape up any browned bits from the pan (this is called deglazing).

In a separate clean saucepan, add the 3 tablespoons sugar and 3 tablespoons beef stock. Heat without stirring until it forms a light caramel. Add the wine from the skillet and stir slowly until well combined.

Let the sauce thicken, then add salt and pepper to taste. Check the flavor and adjust as needed.

Remove the medallions from the oven, carefully take out the toothpicks, spoon the red wine sauce over the medallions, and serve!