In a shallow dish combine flour, salt, and pepper. Dredge the beef cubes with flour, shaking off excess flour. 

Heat the olive oil in a Dutch oven (or large pot) over medium-high heat. Add the beef to the pot and cook just until the meat starts to brown, turning as needed. Do this in 2 or 3 batches, to not crowd the pot. Remove the meat from the pot and set aside.

In the same pot, add the chopped onion, carrots, celery, garlic, and oregano. Cook the vegetables until soft, about 5 minutes, stirring occasionally. 

Deglaze the pan with red wine scraping the fond (the brown bits) from the bottom of the pan. Let simmer and reduce red wine by half. Add tomato paste and stir to coat the vegetables.

Add beef back to the pot with water and beef broth. Stir to combine.

Bring to a boil, add barley and turn down to a simmer for 45-50 minutes, until meat is tender and barley is cooked through. Stir occasionally so the barley won’t stick together. If you find that too much liquid has evaporated or the soup is too thick add more water as necessary until you get the desired consistency.

Remove soup from heat and stir in the kale while the soup is still hot to wilt. Season with salt and pepper, as needed. 

Garnish with parsley, if using.