Preheat broiler with rack set 3 in. from heat. Combine salt, 3/4 tsp. pepper, 2 tbsp. rosemary, and the oil. Oil a rimmed baking sheet. Rub chicken all over with rosemary mixture and put on baking sheet.
Brown bacon in a 12-in. frying pan over medium-high heat, stirring often, 5 to 8 minutes. Transfer to paper towels with a slotted spoon. Pour fat into a heatproof container, then spoon 2 tbsp. fat back into pan.
Broil chicken until just cooked through, turning once, about 8 minutes total. Remove from heat and cover with foil to keep warm.
Meanwhile, cook shallots in bacon pan over medium heat, stirring often, until softened and lightly browned, 5 to 8 minutes. Add raisins and wine to pan; bring to a boil and cook, stirring occasionally, until about 3 tbsp. liquid is left, 1 to 2 minutes. Stir in remaining 1/4 tsp. pepper and 1/2 tsp. rosemary.
Remove from heat and add arugula and bacon. Toss very gently to coat (pan will be very full; use a bowl if you like). Season to taste with salt and pepper. Transfer salad to a platter and arrange chicken paillards on top.