To make the pesto: Combine basil, oregano, garlic, olive oil, Parmesan, and pine nuts in a food processor and purée until smooth. Season with salt and pepper and mix well.
To make the pudding: Heat grill to medium. Tear bread into 1-inch chunks and place in a large shallow baking pan. In a large skillet, cook garlic in hot olive oil over medium heat for 30 seconds. Add tomatoes, basil, and pepper. Cook, uncovered, over medium heat for 2 minutes, stirring occasionally. Add soy milk and bring to a boil. Remove from heat. Pour mix over bread cubes and toss gently to mix. Top with Parmesan cheese. Bake in the grill, with lid closed, for 15 minutes or until heated through. Top with Parmesan cheese and sprigs of fresh basil.
To make the beef: Make 1-inch slits along the edge of the steak, working the tip of the knife to form a pocket. Season with salt and pepper. Stuff Pesto into pockets in meat. Brush steaks with olive oil. Arrange medium coals around a drip pan in a grill with a hood. Test for medium-low heat above the pan.
Place meat on grill rack over drip pan but not over coals. Insert a meat thermometer and lower the grill hood. Grill for 4-5 minutes or until the meat thermometer registers the desired temperature (160˚F for medium, 170˚F for well done). Add more coals as necessary. Let meat stand, covered, for 10 minutes (its temperature will rise slightly).
To serve: Serve the pesto-stuffed beef with the tomato bread pudding.
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