Cook bacon in a large nonstick skillet over medium heat until crisp. Remove bacon from pan and crumble. Set aside, and reserve 1 teaspoon drippings in pan.
Place escarole top-down in pan, and press down gently. Cook over medium-high heat for 3 minutes or until wilted. Flip, and cook 1 minute. Remove to cutting board; coarsely chop escarole, discarding core, and transfer to a large bowl.
Heat olive oil in a pan over medium heat; add minced shallots, and cook 3 minutes or until golden brown. Add balsamic vinegar, orange juice, dried figs, and sugar to pan; stir to dissolve sugar and thicken. Pour dressing and figs over escarole, tossing gently to coat. Season with salt and pepper. Mound on top of chicken; top with cheese and bacon.
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