1/2 cup balsamic vinegar
2 tablespoons Dijon mustard
2 tablespoons olive oil, divided
1 tablespoon honey
1 tablespoon coarsely chopped fresh sage leaves
2 cloves garlic, minced
2 pounds bone-in, skin-on chicken thighs (4 to 6)
Freshly ground black pepper
8 fresh figs, halved or quartered if large
Arrange a rack in the middle of the oven and heat to 350°F.
To make the glaze, whisk the vinegar, mustard, 1 tablespoon of olive oil, honey, sage, and garlic together in a small bowl; set aside.
Pat the chicken thighs dry with paper towels and season on both sides with salt and pepper.
Heat the remaining 1 tablespoon of olive oil in a large cast iron or oven-safe skillet over medium-high heat until the oil is shimmering but not smoking. Add the chicken skin-side down and cook until the fat is rendered and the skin is crisp and golden-brown, adjusting the heat if the skin begins to burn, 6 to 8 minutes.
Flip the chicken thighs and scatter the figs around them. Carefully pour the glaze evenly over the chicken and figs. Transfer the skillet to the oven and cook, spooning some of the glaze in the skillet back over the chicken halfway through, until chicken reaches an internal temperature of 165°F, 10 to 12 minutes total. Serve the chicken with the sauce.