How to Make It
In a small bowl, combine the vinegar with the maple syrup. While whisking constantly, slowly drizzle in 1/4 cup of the oil until incorporated. Season the dressing with salt and pepper.
Heat a large cast-iron skillet. In a large bowl, toss the fig halves with the oregano, thyme and 3 tablespoons of the dressing. Add to the skillet and cook over moderately high heat, turning once and basting with dressing, until the figs are golden and lightly caramelized, 2 to 3 minutes per side. Discard the oregano and thyme. Transfer the figs to a plate.
Rub the halved leek with 2 teaspoons of the oil and season with salt and pepper. Add to the skillet and cook over moderate heat, turning occasionally, until nicely charred and tender, 8 to 10 minutes. Transfer the leek to a cutting board. Let cool, then thinly slice crosswise. Transfer to the large bowl. Repeat with the remaining 2 teaspoons of oil and the radicchio; season with salt and pepper and add to the bowl.
Add the halloumi slices to the skillet and cook over moderate heat, turning once, until golden and crisp, 2 to 3 minutes per side. Add the cheese to the bowl with the leek and radicchio. Add the arugula and the remaining dressing and toss to coat. Mound the salad on plates and arrange the figs around it. Garnish with sesame seeds and serve.
Fresh figs have a very short season. Can't find them? Sub in 8 ounces of red grapes and roast them at 425 for 15 minutes.