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Watercress Salad with Port-Braised Figs and Pickled Onions

['1 tablespoon olive oil', '1 medium-size red onion, thinly sliced (about 2 cups)', '1 tablespoon Champagne vinegar or white wine vinegar', '1 teaspoon sugar', '2 tablespoons red wine vinegar', '1/4 teaspoon salt', '1/8 teaspoon freshly ground black pepper', '1/8 teaspoon sugar', '1/4 cup grapeseed oil or vegetable oil', '2 tablespoons extra-virgin olive oil', '1 750-ml bottle ruby Port', '1 pound dried black Mission figs, stems removed, figs halved', '3 bunches watercress, thick stems removed (about 8 cups)', '6 heads of Belgian endive', 'trimmed', 'cut crosswise into 1/4-inch-thick slices']

Heat oil in large nonstick skillet over medium heat. Add onion and stir 1 minute to coat with oil. Add vinegar and sugar and stir until onion begins to soften slightly, about 3 minutes. Transfer onion to baking sheet or platter; spread in single layer. Sprinkle with salt. Cover and chill at least 8 hours or overnight (onion will turn pink). DO AHEAD: Can be made 2 days ahead. Keep chilled.
Whisk red wine vinegar, 1/4 teaspoon salt, 1/8 teaspoon freshly ground black pepper, and sugar in small bowl. Gradually whisk in both oils. DO AHEAD: Vinaigrette can be made 1 day ahead. Cover and refrigerate. Bring to room temperature and rewhisk before using.
Combine Port and figs in large saucepan. Bring to boil. Reduce heat to medium-low and simmer until figs are plump and tender, about 30 minutes. Using slotted spoon, transfer figs to small bowl. Increase heat to medium-high and boil Port syrup until thickened and reduced to 6 tablespoons, about 8 minutes. Transfer syrup to another small bowl. DO AHEAD: Can be made 2 days ahead. Cover figs and Port syrup separately and chill.
Combine endive, and pickled onion Toss salad with vinaigrette Port syrup over each salad among plates. Sprinkle salads and serve.

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