Dry the beef pieces with some paper towels, and then season with salt and pepper.
Heat 2 teaspoons of oil in the large skillet over medium-high heat. Brown half of the beef, then add to the slow cooker. Repeat with the remaining beef.
Add 2 teaspoons of oil to the large skillet and saute the onions and carrots with 1/4 teaspoon of salt. Cook until the vegetables are soft, about 5 minutes. Stir in the wine, scraping up the brown bits (fond). Simmer until the wine is reduced by half, about 1 minute. Pour it all into the slow cooker.
Add the tomatoes and juice, beef and chicken broth, thyme, and pearl barley and cover. Cook until the beef is tender, about 6 to 7 hours on low or 4 to 5 hours on high.