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Cook bacon pieces in a large nonstick skillet over medium-low, stirring often, until brown and crisp, 8–10 minutes. Using a slotted spoon, transfer bacon to a small bowl.
Pour off all but 2 Tbsp. fat from skillet; save for another use. Add maple syrup to skillet, swirling to combine, and heat over medium-high. Arrange figs in skillet in a single layer, cut side down. Cook, swirling liquid occasionally, until figs are slightly softened and caramelized, about 5 minutes.
Arrange figs cut side up on a platter and press pieces of bacon onto the surface of each fig.
Set the skillet over medium heat, add vinegar, and stir into juices. Bring to a simmer and cook, stirring constantly, until syrupy, about 1 minute. Drizzle syrup over figs, then sprinkle with red pepper.