Press cracked pepper onto both sides of each steak.
Heat olive oil in a large skillet over medium heat. Add steak; cook until browned, 5 to 6 minutes per side. Remove skillet from heat.
Transfer steaks to a serving platter, reserving drippings in the skillet. Stir beef broth and red wine into the skillet, scraping up browned bits. Return to the heat and bring to a boil. Add chard; cover and cook, stirring occasionally, until wilted, about 5 minutes.
Cut steak into serving-size pieces. Serve with chard.