Preheat the oven to 450° F.
Cut the potatoes crosswise into 1/4 inch thick slices. Place the potatoes in cold water to prevent discoloration. When all have been cut, drain well and pat dry.
Place the potatoes in a mixing bowl. Drizzle with about 2 tablespoons of the olive oil. Add the oregano and season with just a pinch of salt and pepper. Toss to coat. Set aside.
Place a heavy medium roasting pan in the preheated oven for about 5 minutes, or until very hot. Remove the pan from the oven and, using 2 tablespoons of olive oil, lightly coat the bottom of the pan.
Place the potatoes in the hot pan, stirring to ensure that they don't stick to the bottom of the pan. Return the pan to the oven. Roast the potatoes for about 20 minutes, or until golden brown but still firm to the touch.
Remove the pan from the oven. Stir in the garlic. Return the pan to the oven for 1 minute.
Remove the pan from the oven and stir in the tomatoes and olives. Return to the oven and cook for 5 minutes, stir, and continue to cook for an additional 5 minutes, or until the potatoes are very tender.
Remove from the oven. Drizzle with the remaining olive oil and season with salt and pepper to taste. Fold in rosemary and serve.
NOTE: "I USE A COMINATION OF KALAMATA, CRACKED GREEN, AND THASSOS OLIVES. TO REMOVE THE PITS, I LIGTLY SMASH THE OLIVE SO THE PIT CAN BE PUSHED OUT
WITHOUT MANGLING THE OLIVE." JIM BOTSACOS.
Reprinted with permission from © James T. Botsacos Jr., The New Greek Cuisine, published by Broadway Books click to read book review
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