Sheet-Pan Chicken Saltimbocca with Roasted Potatoes and Crispy Kale
['8 boneless, skinless chicken breast cutlets (about 2 pounds total)', '1 1/4 teaspoons freshly ground black pepper, divided', '12 small fresh sage leaves, divided', '8 thin slices prosciutto (about 6 ounces)', '1 pound baby new potatoes, sliced in half lengthwise, quartered if large', '1 garlic clove, finely chopped', '3 tablespoons olive oil, divided', '3/4 teaspoon kosher salt, divided', '3 oil-packed anchovy fillets, drained, finely chopped', '1 tablespoon red wine vinegar', '2 teaspoons honey', '1 bunch curly kale (about 8 ounces), ribs and stems removed, coarsely chopped', '2 (18x13") rimmed baking sheets']
Position racks in upper and lower thirds of oven and preheat to 425°F. Arrange chicken cutlets in a single layer on rimmed baking sheet and season with 1/2 tsp. pepper. Place 1 sage leaf on top of each cutlet, then wrap each in 1 slice of prosciutto, starting from the top and wrapping in a single layer, making sure cutlet stays flat.
Finely chop remaining 4 sage leaves and toss with potatoes, garlic, 1 Tbsp. oil, 1/2 tsp. salt, and 1/2 tsp. pepper on second rimmed baking sheet.
Cook chicken in upper third of oven and potatoes in lower third until prosciutto is crisp and an instant-read thermometer inserted into the thickest part of chicken registers 165°F, 12-14 minutes.
Meanwhile, whisk anchovies, vinegar, honey, and remaining 2 Tbsp. oil, 1/4 tsp. salt, and 1/4 tsp. pepper in a large bowl; add kale and toss to coat.
Remove both baking sheets from oven; let chicken rest. Spread kale evenly over potatoes and return to upper third of oven. Roast until potatoes are tender and kale is browned at edges, about 5 minutes more.
Divide chicken among 4 plates. Serve potatoes and kale alongside.
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