1. Soak four 6-inch bamboo skewers in water for 30 minutes and preheat grill to medium.
2. Cut escarole lengthwise, through core, into 4 wedges. Season with salt and pepper. Wrap each wedge tightly with 2 slices of bacon; secure with skewers and brush with 1/4 cup olive oil. Place bundles skewered side down and covered with a disposable aluminum pan on grill. Cook, turning occasionally until bacon is crisp, about 12 minutes.
3. Lightly brush bread with additional olive oil, season with salt and black pepper to taste and char on grill, about 1 minute per side. Remove and rub bread with cut side of tomato halves until toasts are saturated with tomato's juices.
4. Top each crostini with an escarole bundle and serve with a lemon wedge.
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