Heat the oven to 325F. Cut the tomatoes into 1-inch chunks, and place on a baking sheet with parchment or cooking spray. Sprinkle with the salt and pepper. Roast for 1.5 - 2 hours until tomatoes are dried, wilted, and slightly dark at the edges.
When tomatoes are roasted or nearly roasted, prepare the rest of the ingredients. Add the kale to a large bowl with a sprinkle of salt and massage for 30 seconds or so to tenderize. Add the olive oil to a small pan and mince the garlic. Over medium-low heat, add the garlic to the oil and stir until just fragrant, then turn the heat off and let the oil cool.
To the kale, add the orzo and garlic oil. Stir and taste; add salt to your preference. Very gently stir in the tomatoes and most of the parmesan. Top with the rest of the parmesan and serve.
Best served warm or at room temperature, but also can be served hot or cold.