In a large skillet over medium heat, toss spinach with 1 tsp. olive oil and pinch of salt for about 1 minute to wilt. Transfer to strainer and allow water to drip out. Squeeze out any excess.
In a small bowl combine cream cheese, chives and garlic powder.
Season chicken with remaining salt and freshly ground pepper. Place cutlets on a flat surface. Divide the cream cheese mixture evenly between the chicken pieces, spreading it on one side of each cutlet, almost to the edges.
Top the cream cheese mixture with 1 slice of ham and equal portions of spinach down the center of the breast. Fold cutlet in half lengthwise, and roll up. Secure with toothpicks.
Heat 1 Tbs. olive oil in skillet over medium-high. Cook chicken rolls approximately 10 to 12 minutes, turning until golden brown and cooked through. Set aside chicken loosely covered with foil for about 5 minutes.
Slice chicken into pinwheels and serve.