Place the tenderloin lengthwise on a cutting board. With your knife parallel to the board, cut along the middle without slicing all the way through. Open the meat like a book.
Place the tenderloin between two sheets of plastic wrap and pound to roughly ½-inch thick using the flat side of a meat mallet.
Season evenly with Greek oregano, kosher salt, and coarse black pepper. Lay provolone slices over the meat. Spread Mediterranean olive bruschetta or tapenade on top, then layer roasted red bell pepper strips.
Roll the tenderloin tightly lengthwise into a pinwheel. Wrap in plastic wrap and refrigerate at least 1 hour to help it hold its shape.
Preheat oven to 425°F and place a 12-inch cast iron skillet inside to heat.
Remove tenderloin from plastic wrap. Cut six 12-inch pieces of butcher’s twine. Evenly space the twine along the roll, about 1–1½ inches apart, and tie to secure. Trim any excess twine. Slice between each tie to create 6 individual pinwheels.
Carefully remove the hot skillet from the oven. Arrange pinwheels in the skillet and drizzle with olive oil. Roast 25–30 minutes, or until a meat thermometer reads 130–135°F for medium-rare.
Remove from oven and let rest 5 minutes. Carefully remove twine before serving. Plate with a green salad and your favorite sides for a Mediterranean-inspired, visually stunning meal.