1 1/4poundssmall tomatoes-chopped, plus 14 cup finely diced
1/2cupkalamata olives- chopped
3Tablespoonsfresh oregano- chopped
kosher salt and pepper
4ouncesfeta cheese- coarsely crumbled
1/4cuppeppadew peppers- chopped (optional)
In a 12-inch nonstick skillet over medium-high, heat 1 Tablespoon of the olive oil until shimmering. Add half the shrimp in an even layer and cook without disturbing until deep golden brown on the bottoms, 1 to 2 minutes. Stir and cook until the shrimp are pink and opaque on all sides, another 20 or 30 seconds. Transfer to a medium bowl. Repeat with 1 Tablespoon of the remaining oil and the remaining shrimp. Set aside.
Add the remaining 1 Tablespoon oil to the pan and heat over medium-high until shimmering. Add the garlic, fennel and red pepper flakes and cook, stirring constantly until the garlic is light golden brown, about 20 seconds. Add the wine and cook, stirring, until the liquid is almost evaporated, 30 to 60 seconds. Add the chopped tomatoes, olives and 1 1/2 teaspoons of salt. Cook, stirring until the tomatoes have broken down in a sauce, 6 to 7 minutes.
Remove the pan from heat. Stir in 2 tablespoons of the oregano, then taste and season with salt and pepper. Return the shrimp to the skillet, along with the accumulated juices. Cover the pan and let stand until the shrimp are heated through, about 1 minute.
Transfer to a serving dish. Sprinkle with feta, finely diced tomatoes, the Peppadews (if using) and the remaining oregano.
Don't use pre-crumbled feta. The cheese plays a rpominent role in this dish, so good-quality feta sold in blocks is important. Greek, bulgarian, French and Israeli feta all work well.